- 3-PHENYLSULPHONYL-QUINOLINE DERIVATIVES AS AGENTS FOR TREATING PATHOGENIC BLOOD VESSELS DISORDERS
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The disclosure provides compounds, and compositions, including pharmaceutical compositions, kits that include the compounds, and methods of using (or administering) and making the compounds. The disclosure further provides compounds or compositions thereof for use in a method of modulating PLXDC1 (TEM7) and/or PLXDC2 or killing pathogenic blood vessles. The disclosure further provides compounds or compositions thereof for use in a method of treating a disease, disorder, or condition that is mediated, at least in part, by PEDF receptors or by angiogenesis.
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Paragraph 0326
(2021/04/23)
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- Sulfonimidesversusketosulfonamides as epoxidized imidazolium counterions: Towards a new generation of ionic liquid monomers
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The design of novel ionic liquid monomers with attractive properties represents a real challenge in the field of poly(ionic liquid)s (PILs). Here, we describe a comparative study of the synthesis of original PIL precursors from various sulfonimides or ketosulfonamides as unprecedented counteranions of imidazolium ILs. These salts were submitted to the Prilezhaev reaction and a first insight into the intrinsic properties of these new epoxy monomers was unveiled, in particular the thermal stability of these advanced epoxy salts by comparison with traditional counterions.
- Chardin,Durand,Jarsalé,Rouden,Livi,Baudoux
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supporting information
p. 2953 - 2957
(2021/02/26)
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- N-ARYL SULFONAMIDE DERIVATIVES AS VACCINE ADJUVANT
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Bis-aryl sulfonamide compounds and methods of using those compounds, e.g., in a method of enhancing or prolonging an immune response, are provided. For example, the compounds may be employed with a vaccine and optionally at least one other adjuvant and/or one or more TLR ligands, at least one MAP kinase inhibitor, or any combination thereof.
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Page/Page column 101-102
(2021/02/26)
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- Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst
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Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.
- Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias
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supporting information
p. 20543 - 20550
(2021/08/12)
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- Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
- Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
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- Synthesis, biological evaluation, and enzyme assay of some 5-N-substituted-2-N-(arylsulphonyl)-L(+)glutamines as potential anticancer agents
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Thirty 5-N-substituted-2-N-(arylsulphonyl)-L(+)glutamines were synthesized and evaluated biologically for their anticancer activities. The best active compound of this series showed 92.92% inhibition of tumor weight against Ehrlich Ascites Carcinoma cells. The most active compound was proved to be a competitive inhibitor of glutaminase in the enzyme assay. The best active compound may be a starting point to generate 'lead' for further exploration.
- Jha, Tarun,Samanta, Soma,Halder, Amit Kumar,Adhikari, Nilanjan,Abdul Amin,Sanyal, Arpita,Mukherjee, Tanmoy
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p. 1259 - 1264
(2020/12/04)
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- Design, synthesis, molecular docking and in vitro evaluation of N-(4-methoxyphenylsulfonyl)pyrrolidine-2-carboxylic acid analogues as antiangiogenic and anticancer agents on multiple myeloma
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A series of N-(4-methoxyphenylsulfonyl)pyrrolidine-2-carboxylic acid analogs were designed as bioisosteres of a major metabolite of thalidomide, i.e., N-(o-carboxybenzoyl)-D,L-glutamic acid. Compounds 2b, 2d, 2f, 2i and 2k exhibited anticancer activity on multiple myeloma (RPMI 8226) by MTS assay and were tested for primary antiangiogenic activity on HUVEC cell line by MTT assay. Compound 2f was excluded from further study as it was found to be cytotoxic to normal epithelial cells. 2b, 2d, 2i and 2k were found to have primary antiangiogenic activity along with low cytotoxicity on normal vero cells in MTT assay indicating selective cytotoxicity towards highly angiogenic multiple myeloma. Antiproliferative assay of compounds 2b, 2d, 2i and 2k on HUVECs was carried out using the dye exclusion method with trypan blue. Molecular docking study of compound 2b calculated the binding energy -89.78 kcal/mol and displayed five hydrogen bonds with critical amino acid residues. The compounds are potential candidate drugs for advanced investigations.
- Sarker,Ghosh,Mishra,Saha,Sen
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p. 3079 - 3086
(2021/01/06)
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- Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts
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We report herein a general and practical copper-catalyzed fluorosulfonylation reaction of a wide range of abundant arenediazonium salts to smoothly prepare various arenesulfonyl fluorides using the 1,4-diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct as a convenient sulfonyl source in combination with KHF2 as an ideal fluorine source and without the need for additional oxidants. Interestingly, the electronic character of the arene ring in the starting arenediazonium salts has a significant impact on the reaction mechanistic pathway.
- Liu, Yongan,Yu, Donghai,Guo, Yong,Xiao, Ji-Chang,Chen, Qing-Yun,Liu, Chao
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supporting information
p. 2281 - 2286
(2020/03/13)
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- Proline-Based Allosteric Inhibitors of Zika and Dengue Virus NS2B/NS3 Proteases
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The NS2B/NS3 serine proteases of the Zika and Dengue flaviviruses are attractive targets for the development of antiviral drugs. We report the synthesis and evaluation of a new, proline-based compound class that displays allosteric inhibition of both proteases. The structural features relevant for protease binding and inhibition were determined to establish them as new lead compounds for flaviviral inhibitors. Based on our structure-activity relationship studies, the molecules were further optimized, leading to inhibitors with submicromolar IC50 values and improved lipophilic ligand efficiency. The allosteric binding site in the proteases was probed using mutagenesis and covalent modification of the obtained cysteine mutants with maleimides, followed by computational elucidation of the possible binding modes. In infected cells, antiviral activity against Dengue virus serotype 2 using prodrugs of the inhibitors was observed. In summary, a novel inhibitor scaffold targeting an allosteric site shared between flaviviral NS2B/NS3 proteases is presented whose efficacy is demonstrated in vitro and in cellulo.
- Millies, Benedikt,Von Hammerstein, Franziska,Gellert, Andrea,Hammerschmidt, Stefan,Barthels, Fabian,G?ppel, Ulrike,Immerheiser, Melissa,Elgner, Fabian,Jung, Nathalie,Basic, Michael,Kersten, Christian,Kiefer, Werner,Bodem, Jochen,Hildt, Eberhard,Windbergs, Maike,Hellmich, Ute A.,Schirmeister, Tanja
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p. 11359 - 11382
(2019/12/24)
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- Structure-Activity Relationship Studies to Identify Affinity Probes in Bis-aryl Sulfonamides That Prolong Immune Stimuli
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Agents that safely induce, enhance, or sustain multiple innate immune signaling pathways could be developed as potent vaccine adjuvants or coadjuvants. Using high-throughput screens with cell-based nuclear factor κB (NF-κB) and interferon stimulating response element (ISRE) reporter assays, we identified a bis-aryl sulfonamide bearing compound 1 that demonstrated sustained NF-κB and ISRE activation after a primary stimulus with lipopolysaccharide or interferon-α, respectively. Here, we present systematic structure-activity relationship (SAR) studies on the two phenyl rings and amide nitrogen of the sulfonamide group of compound 1 focused toward identification of affinity probes. The murine vaccination studies showed that compounds 1 and 33 when used as coadjuvants with monophosphoryl lipid A (MPLA) showed significant enhancement in antigen ovalbumin-specific immunoglobulin responses compared to MPLA alone. SAR studies pointed to the sites on the scaffold that can tolerate the introduction of aryl azide, biotin, and fluorescent rhodamine substituents to obtain several affinity and photoaffinity probes which will be utilized in concert for future target identification and mechanism of action studies.
- Chan, Michael,Lao, Fitzgerald S.,Chu, Paul J.,Shpigelman, Jonathan,Yao, Shiyin,Nan, Jason,Sato-Kaneko, Fumi,Li, Vicky,Hayashi, Tomoko,Corr, Maripat,Carson, Dennis A.,Cottam, Howard B.,Shukla, Nikunj M.
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supporting information
p. 9521 - 9540
(2019/11/11)
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- High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides
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In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.
- Sohrabnezhad, Samira,Bahrami, Kiumars,Hakimpoor, Farahman
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p. 256 - 264
(2019/02/06)
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- Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4
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Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.
- Gómez-Palomino, Alejandro,Cornella, Josep
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supporting information
p. 18235 - 18239
(2019/11/13)
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- Synthesis and insecticidal activity in vitro and vivo of novel benzenesulfonyl derivatives based on potent target subunit H of V-ATPase
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Two lead compounds with benzenesulfonamide were found through virtual screening based on the 3D structure of the subunit H of V-ATPase in previous study. 74 benzenesulfonyl derivatives were synthesized and their insecticidal activities were evaluated. The derivatives with propargyl substituents exhibit excellent insecticidal activities against Mythimna separata Walker. The LD50 values of compounds A5.7 (28.0 μg·g?1) and B5.7 (36.4 μg·g?1) were significantly less than that of Celangulin V (344.0 μg·g?1). Furthermore, Isothermal Titration Calorimetry (ITC) data indicate there is a strong binding affinity between A5.7 and V-ATPase Subunit H. These results demonstrate that it is a practical way to develop pesticides targeting at H subunit of V-ATPase.
- Yang, Chaofu,Li, Xiaoting,Wei, Jielu,Zhu, Feng,Gang, Fangli,Wei, Shaopeng,Zhao, Yunlong,Zhang, Jiwen,Wu, Wenjun
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p. 3164 - 3167
(2018/09/11)
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- Possible anticancer agents: synthesis, pharmacological activity, and molecular modeling studies on some 5-N -Substituted-2-N-(substituted benzenesulphonyl)-L(+)Glutamines
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On the basis of our earlier work, fortyone 5-N-substituted-2N-(substituted benzenesulphonyl)-L(+)glutamines were synthesized and screened for cancer cell inhibitory activity. The best active compounds showed 91% tumor cell inhibition, whereas other three compounds showed more than 80% inhibition. Two-dimensional quantitative structure–activity relationship modeling and three-dimensional quantitative structure–activity relationship k-nearest neighbor molecular field analysis studies were done to get an insight into structural requirements toward further improved anticancer activity. Considering the fact that these compounds are competitive inhibitors of glutaminase, a molecular docking study followed by molecular dynamic simulation analysis were performed. The work may help to develop new anticancer agents.
- Jha, Tarun,Basu, Soumya,Halder, Amit Kumar,Adhikari, Nilanjan,Samanta, Soma
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p. 1437 - 1458
(2017/06/05)
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- Novel sulfonamide compound, preparation method, and use of novel sulfonamide compound as protein tyrosine phosphatase 1B inhibitor
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The invention relates to a novel sulfonamide compound in a structure of a general formula I as shown in the specification, or pharmaceutically acceptable salt and a preparation method of the novel sulfonamide compound, and further relates to a drug composition containing the compound as shown as the general formula I or the pharmaceutically acceptable salt of the compound, and a use of the compound or the pharmaceutically acceptable salt for preparing a drug for preventing and/or treating symptoms or diseases such as hyperglycemia and diabetes mellitus type 2 since the compound as shown as the general formula I or the pharmaceutically acceptable salt of the compound has activity of inhibiting a protein tyrosine phosphatase 1B (PTP 1B).
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Paragraph 0019
(2017/12/29)
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- Aromatic Chlorosulfonylation by Photoredox Catalysis
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Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.
- Májek, Michal,Neumeier, Michael,Jacobi von Wangelin, Axel
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p. 151 - 155
(2017/01/17)
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- Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH
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A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.
- Silva-Cuevas, Carolina,Perez-Arrieta, Carlos,Polindara-García, Luis A.,Lujan-Montelongo, J. Armando
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supporting information
p. 2244 - 2247
(2017/05/16)
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- Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides
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A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.
- Yang, Zhanhui,Xu, Wei,Wu, Qiuyue,Xu, Jiaxi
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p. 3051 - 3057
(2016/04/26)
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- Design of novel CSA analogues as potential safeners and fungicides
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Study of safeners has been seldom reported in literature. In this work, a series of novel acylsulfamoylbenzamide analogues was designed and synthesized with newly developed safener cyprosulfamide (CSA) as the leading compound. The activity assay against the herbicide thiencarbazone-methyl (TCM) on maize revealed that fifteen compounds showed better protective effect than CSA on the fresh weight of aerial parts, twelve compounds exhibited better activity on the dry weight of aerial parts. Remarkably, two compounds (6Ih, 7II) had protective effect on the four aspects of TCM treated maize. Further antifungal assay showed their excellent activity against Physollospora piricola. The structure-activity relationships of CSA analogues as safeners and fungicides were discussed and it might be valuable for further molecular modification of new CSA analogues.
- Zheng, Yang,Liu, Bin,Gou, Zhaopin,Li, Yao,Zhang, Xiao,Wang, Yanqing,Yu, Shujing,Li, Yonghong,Sun, Dequn
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supporting information
p. 791 - 794
(2015/02/19)
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- An efficient method for the preparation of sulfonyl chlorides: Reaction of disulfides or thiols with sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals
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The reaction of disulfides or thiols with sodium hypochlorite pentahydrate in acetic acid efficiently provided the corresponding sulfonyl chlorides in high yields.
- Okada, Tomohide,Matsumuro, Hiroaki,Iwai, Toshiaki,Kitagawa, Saori,Yamazaki, Kento,Akiyama, Tomomi,Asawa, Tomotake,Sugiyama, Yukihiro,Kimura, Yoshikazu,Kirihara, Masayuki
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p. 185 - 187
(2015/02/19)
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- METHOD FOR PRODUCING SULFONYL CHLORIDE COMPOUNDS
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PROBLEM TO BE SOLVED: To provide a production method which enables safe and simple production of sulfonyl chloride compounds in high yields, which are useful as intermediates for medicines, agrochemicals, functional materials, and the like. SOLUTION: Provided is a method for producing sulfonyl chloride compounds comprising oxidation of thiols or disulfides in the presence of an oxidizing agent to produce sulfonyl chloride compounds. As the oxidizing agent is used sodium hypochlorite, and the reaction is performed with the pH of the reaction system adjusted to a neutral or acidic value of pH 7 or less. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0031; 0033
(2018/11/22)
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- Novel, potent, selective and cellular active ABC type PTP1B inhibitors containing (methanesulfonyl-phenyl-amino)-acetic acid methyl ester phosphotyrosine mimetic
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Protein tyrosine phosphatase 1B (PTP1B) which plays an important role in the negative regulation of insulin and leptin pathway has emerged as a novel promising therapeutic target for the treatment of type 2 diabetes mellitus and obesity. Upon careful study, a series of novel scaffold and simple synthesis method inhibitors were discovered based on the analysis of X-ray crystal structures of PTP1B/inhibitor complexes and docking simulations. Among them, compound P7 exhibited high inhibitory activity (IC50 = 222 nM) with moderate selectivity (8-fold) over T-cell PTPase (TCPTP) through interacting with the A, B and C binding sites of PTP1B enzyme. Further studies on cellular activities revealed that compound P7 could enhance insulin-mediated IRβ phosphorylation and insulin-stimulated glucose uptake.
- Liu, Peihong,Du, Yongli,Song, Lianhua,Shen, Jingkang,Li, Qunyi
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p. 7079 - 7088
(2015/11/11)
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- Oxidation of disulfides with electrophilic halogenating reagents: Concise methods for preparation of thiosulfonates and sulfonyl halides
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The reaction of aromatic or benzylic disulfides with 2.5 equiv of Selectfluor in acetonitrile/water (10:1) at room temperature efficiently produced the corresponding thiosulfonates. Conversely, the reaction of disulfides with 6.5 equiv of Selectfluor or thiosulfonates with 4.5 equiv of Selectfluor in refluxing acetonitrile/water (10:1) provided sulfonyl fluorides in high yields. Accufluor and FP-T300 are also effective in preparing sulfonyl fluorides from disulfides under the similar reaction conditions. Sulfonyl chlorides or sulfonyl bromides were effectively obtained from the reaction of disulfides with 6 equiv of either N-chlorosuccinimide or N-bromosuccinimide in acetonitrile/water (10:1) at room temperature. Some other electrophilic chlorinating or brominating reagents are also able to be used instead of N-chlorosuccinimide or N-bromosuccinimide for the syntheses of sulfonyl halides from disulfides. These reactions of disulfides with electrophilic halogenating reagents are convenient methods to prepare thiosulfonates and sulfonyl halides.
- Kirihara, Masayuki,Naito, Sayuri,Nishimura, Yuki,Ishizuka, Yuki,Iwai, Toshiaki,Takeuchi, Haruka,Ogata, Tomomi,Hanai, Honoka,Kinoshita, Yukari,Kishida, Mari,Yamazaki, Kento,Noguchi, Takuya,Yamashoji, Shiro
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p. 2464 - 2471
(2014/04/03)
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- Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water
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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.
- Madabhushi, Sridhar,Jillella, Raveendra,Sriramoju, Vinodkumar,Singh, Rajpal
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p. 3125 - 3131
(2014/06/10)
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- Synthesis of 5-(ethylsulfonyl)-2-methoxyaniline: An important pharmacological fragment of VEGFR2 and other inhibitors
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Background: 5-(Ethylsulfonyl)-2-methoxyaniline (5) is part of the structure in 131 compounds possessing different biological activities. In most cases, they have antitumor properties (112 compounds). Other compounds are described as cardiovascular agents, ion-channel blockers, nervous-system blockers, anti-inflammatory agents, or antidiabetic, antiosteoporotic and hypolipemic species. Compound 5 is a precursor of different protein-kinase inhibitors or enzyme modulators (EGFR, PDGFR, ckit, CDK 2 and 4, MMPs 2, 3, 9 and 13, etc.). The structure of 5 represents a fragment for several powerful inhibitors of VEGFR2, a key angiogenic receptor. Antiangiogenic inhibitors slow down or stop new blood-vessel formation from pre-existing vasculature. Some antiangiogenic drugs inhibiting the VEGFR2 receptor are successfully used in clinics for the treatment of several types of tumours in synergy with chemotherapy (e.g., Nexavar from Bayer, Sutent from Pfizer and Votrient from GlaxoSmithKline, approved by the FDA in 2005, 2006 and 2009, respectively). The structure of 5 is an important pharmacophoric fragment of potent VEGFR2 inhibitors (e.g., AAZ from PDB complex 1Y6A, enzymatic IC50 = 22 nM). Up to now, 25 VEGFR2 inhibitors possessing a fragment of 5 can be found in the literature. Despite the high significance of 5-(ethylsulfonyl)-2-methoxyaniline (5) its preparation has not yet been described. Results: Here we have developed a convenient synthesis of important polyheterosubstituted aniline 5 starting from commercially available 4-methoxybenzene-1-sulfonyl chloride (1) in four steps and 59% overall yield. The target 5-(ethylsulfonyl)-2-methoxyaniline (5) and its synthetic intermediates 2-4 together with a new compound 5-(ethylsulfonyl)-2-methoxy-1,3-dinitrobenzene (4a) have been precisely physicochemically characterised.
- Murar, Miroslav,Addova, Gabriela,Bohac, Andrej
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p. 173 - 179
(2013/03/29)
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- Design, synthesis, and biological evaluation of 1,2,4-triazole bearing 5-substituted biphenyl-2-sulfonamide derivatives as potential antihypertensive candidates
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A series of novel 1,2,4-triazole bearing 5-substituted biphenyl-2- sulfonamide derivatives were designed and synthesized to develop new angiotensin II subtype 2 (AT2) receptor agonists as novel antihypertensive candidates. It was found that 14f (IC50 = 0.4 nM) and 15e (IC 50 = 5.0 nM) displayed potent AT2 receptor affinity and selectivity in binding assays. Biological evaluation in vivo suggested that 14f is obviously superior to that of reference drug losartan in RHRs, and meanwhile, 14f has no significant impact on heart rate. The interesting activities of these compounds may make them promising candidates as antihypertensive agents.
- Liu, Jie,Liu, Qin,Yang, Xue,Xu, Shengtao,Zhang, Hengyuan,Bai, Renren,Yao, Hequan,Jiang, Jieyun,Shen, Mingqin,Wu, Xiaoming,Xu, Jinyi
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p. 7742 - 7751
(2014/01/06)
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- Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids
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A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.
- Debergh, J. Robb,Niljianskul, Nootaree,Buchwald, Stephen L.
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supporting information
p. 10638 - 10641
(2013/08/23)
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- One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T
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A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine-T (=N-chlorotosylamide=N-chloro-4- methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.
- Maleki, Behrooz,Hemmati, Saba,Tayebee, Reza,Salemi, Sirous,Farokhzad, Yasaman,Baghayeri, Mehdi,Zonoz, Farrokhzad Mohammadi,Akbarzadeh, Elahe,Moradi, Rohollah,Entezari, Azam,Abdi, Mohammad Reza,Ashrafi, Samaneh Sedigh,Taimazi, Fereshteh,Hashemi, Majid
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p. 2147 - 2151
(2013/12/04)
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- Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles
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H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and di-sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. Georg Thieme Verlag Stuttgart · New York.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
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experimental part
p. 316 - 322
(2012/03/26)
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- Convenient one-pot synthesis of sulfonamides from thiols and disulfides using 1,3-dichloro-5,5-dimethylhydantoin (DCH)
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A convenient synthesis of sulfonamides from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with 1,3-dichloro-5,5-dimethylhydantoin (DCH) under Nbenzyl-trimethylammonium chloride and water. The sulfonyl chlorides are then further allowed to react with excess amine in the same reaction vessel.
- Veisi, Hojat
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experimental part
p. 383 - 386
(2012/04/23)
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- Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) as efficient reagents for the direct oxidative conversion of thiols and disulfides to sulfonyl chlorides
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Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) were found to be mild and efficient reagents for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good-to-excellent yields through the oxidative chlorination. The overall process is simple and practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides. Copyright
- Veisi, Hojat,Sedrpoushan, Alireza,Hemmati, Saba,Kordestani, Davood
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experimental part
p. 769 - 775
(2012/06/30)
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- Synthesis of sulfonyl chlorides and thiosulfonates from H2O 2-TiCl4
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A new method is described for the oxidative chlorination of thiols to sulfonyl chlorides using titanium tetrachloride in combination with the oxidant hydrogen peroxide. Direct conversion of thiols into their corresponding thiosulfonates is also reported. Good to excellent yields, short reaction times, high efficiencies, cost-effectiveness, and, facile isolation of the desired products make the present methodology a practical alternative.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Khaledian, Donya
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experimental part
p. 354 - 358
(2012/01/19)
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- TAPC-promoted synthesis of sulfonyl chlorides from sulfonic acids
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A novel and efficient method is described for the preparation of sulfonyl chlorides from sulfonic acids using TAPC as chlorinating agent. Mild reaction conditions, shorter reaction times, high efficiencies, cost-effectiveness, and facile isolation of the desired products make the present methodology a practical alternative and will provide a valuable synthetic tool for various pharmaceutical applications. Georg Thieme Verlag Stuttgart · New York.
- Bahrami, Kiumars
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experimental part
p. 2671 - 2674
(2011/12/04)
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- A general and mild two-step procedure for the synthesis of aryl and heteroaryl sulfonamides from the corresponding iodides
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A mild two-step preparation of aryl and heteroaryl sulfonyl chlorides and sulfonamides from their corresponding iodides is developed. Acid labile functionalities are shown to be stable under both the copper-catalysed coupling and the subsequent oxidative chlorination.
- Ho, Danny K.H.,Chan, Lily,Hooper, Alice,Brennan, Paul E.
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experimental part
p. 820 - 823
(2011/03/18)
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- Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide as efficient reagents to direct oxidative conversion of thiols and disulfide to sulfonyl chlorides
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Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) (PCBS) and N,N,N',N'-Tetrachlorobenzene-1,3- disulfonamide (TCBDA) were found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through the oxidative chlorination. The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive, and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.
- Veisi, Hojat,Ghorbani-Vaghei, Ramin,Mahmoodi, Jafar
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experimental part
p. 3692 - 3695
(2012/01/11)
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- Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide
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A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel. Georg Thieme Verlag Stuttgart - New York.
- Veisi, Hojat,Ghorbani-Vaghei, Ramin,Hemmati, Saba,Mahmoodi, Jafar
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experimental part
p. 2315 - 2320
(2011/10/13)
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- A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides
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2,4-Dichloro-5,5-dimethylhydantoin (DCDMH) was found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through oxidative chlorination. The method is suitable for many types of sulfur substrates (thiols, disulfides, and benzylic sulfides). The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.
- Pu, Yu-Ming,Christesen, Alan,Ku, Yi-Yin
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supporting information; experimental part
p. 418 - 421
(2010/03/04)
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- Preparation of arylsulfonyl chlorides by chlorosulfonylation of in situ generated diazonium salts using a continuous flow reactor
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A new flow procedure for the preparation of arylsulfonyl chlorides from aniline starting materials is described. The reaction conditions are mild, requiring no added acid and are amenable to continuous flow processing, in a safe, easily scalable and less labour intensive way than the corresponding batch method.
- Malet-Sanz, Laia,Madrzak, Julia,Ley, Steven V.,Baxendale, Ian R.
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experimental part
p. 5324 - 5332
(2011/01/12)
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- A novel, practical synthesis of sulfonyl chlorides from thiol and disulfide derivatives
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Hydrogen peroxide, in the presence of zirconium tetrachloride, is a very efficient reagent for the direct oxidative conversion of thiol and disulfide derivatives into the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Excellent yields, very short reaction times, mild reaction conditions, and the avoidance of harsh reagents are the main advantages of this method.
- Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Soheilizad, Mehdi
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experimental part
p. 2773 - 2776
(2010/02/28)
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- Direct conversion of thiols to sulfonyl chlorides and sulfonamides
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(Chemical Equation Presented) H2O2 in combination with SOCl2 proved to be a highly reactive reagent for the direct oxidative conversion of thiol derivatives to the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Upon reaction with amines, the corresponding sulfonamides were obtained in excellent yields and in very short reaction times.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Soheilizad, Mehdi
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supporting information; experimental part
p. 9287 - 9291
(2010/03/04)
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- Chlorotrimethylsilane-nitrate salts as oxidants: Direct oxidative conversion of thiols and disulfides to sulfonyl chlorides
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(Chemical Equation Presented) A mixture of nitrate salt and chlorotrimethylsilane is found to be a mild and efficient reagent for the direct oxidative conversion of thiols (1) and disulfides (2) to the corresponding sulfonyl chlorides (3) in excellent yields through oxidative chlorination. Sulfides and sulfoxides were also found to undergo oxidation to sulfones under similar reaction conditions. In most cases these reactions are highly selective, simple, and clean, affording products in high yield and purity.
- Prakash, G. K. Surya,Mathew, Thomas,Panja, Chiradeep,Olah, George A.
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p. 5847 - 5850
(2008/02/09)
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- Sulfonyl chloride formation from thiol derivatives by N-chlorosuccinimide mediated oxidation
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Oxidation of several thiol derivatives by a combination of N-chlorosuccinimide and dilute hydrochloric acid proceeded smoothly, affording the corresponding sulfonyl chlorides in good yield. Georg Thieme Verlag Stuttgart.
- Nishiguchi, Atsuko,Maeda, Kazuhiro,Miki, Shokyo
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p. 4131 - 4134
(2008/03/13)
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- Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists
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The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.
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- Reaction of arendiazonium salts and SO2with α-nitroolefins
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In reaction of β-nitrostyrene and 2-(2-nitrovinyl)furan with arenediazonium chlorides and SO2 in the presence of copper(II) chloride products were obtained resulting from addition of arylsulfonyl group and a hydrogen atom across the C=C bond: 2-nitro-1-phenylethylsulfonylarenes and 2-(1-arylsulfonyl-2-nitroethyl)furans respectively. An anion-radical mechanism of the reaction was suggested.
- Bilaya,Obushak,Buchinskii,Ganushchak
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p. 191 - 194
(2007/10/03)
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- Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides
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A series of arene and heteroarene sulfonamides were prepared in one vessel from aryl and heteroaryl bromides via conversion into the corresponding Grignard reagents using either magnesium or isopropylmagnesium chloride and subsequent reaction with sulfur dioxide, sulfuryl chloride, and an amine.
- Pandya, Rina,Murashima, Takashi,Tedeschi, Livio,Barrett, Anthony G. M.
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p. 8274 - 8276
(2007/10/03)
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- Cyclic amine compounds as CCR5 antagonists
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A compound of formula (I) (wherein R1is a hydrogen atom, a hydrocarbon group which may be substituted, a non-aromatic heterocyclic group which may be substituted, R2is a hydrocarbon group which may be substituted, a non-aromatic heterocyclic group which may be substituted, or R1and R2may combine to each other together with A to form a heterocyclic group which may be substituted; A is N or N+—R5.Y?(R5is a hydrocarbon group; Y?is a counter anion); R3is a cyclic hydrocarbon group which may be substituted or a heterocyclic group which may be substituted; n is 0 or 1; R4is a hydrogen atom, a hydrocarbon group which may be substituted, a heterocyclic group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, or an amino group which may be substituted, E is a divalent aliphatic hydrocarbon group which may be substituted by group(s) other than oxo; G1is a bond, CO or SO2; G2is CO, SO2, NHCO, CONH or OCO; J is methine or a nitrogen atom; and each of Q and R is a bond or a divalent C1-3aliphatic hydrocarbon which may be substituted; provided that J is methine when G2is OCO, that one of Q and R is not a bond when the other is a bond and that each of Q and R is not substituted by oxo group(s) when G1is a bond) or a salt thereof has a potent CCR5 antagonistic activity and can be advantageously used for the treatment or prevention of infectious disease of various HIV in human (e.g. AIDS).
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- Benzene sulfonamides as PDE-V inhibitors for the use against erectile dysfunction
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The compounds of formula (I) wherein X, R0, R1, R2, n and m have the meanings given in the specification, are useful as active ingredients in pharmaceutical compositions. The invention relates to the use of said compounds as a medicament and for the manufacture of a medicament for the treatment of erectile dysfunction.
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Page 10-11;14
(2010/01/31)
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- Bispiperidines as antithrombotic agents
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Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents
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- Remarkably Mild and Simple Preparations of Sulfinates, Sulfonyl Chlorides and Sulfonamides from Thioanisoles
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New and high yielding procedures to convert thioanisoles into versatile sulfonyl chloride derivatives were developed by strategically taking advantage of the Pummerer reaction.
- De Vleeschauwer, Marc,Gauthier, Jacques Yves
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p. 375 - 377
(2007/10/03)
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