- Low-Resolution Microwave Studies of Substituted Ethyl- and Isopropylbenzenes
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A single conformation exists in ethylbenzenes with the ethyl C-C bond lying in a plane orthogonal to the benzene ring.This conclusion results from the observation that asymmetrically substituted ethylbenzenes each display only a single band series in low-resolution microwave (LRMW) spectra whereas any other conformation of the ethylphenyl fragment would result in two spectroscopically distinguishable species.LRMW spectra of isopropylbenzene derivatives display three spectroscopically distinguishable band series, two of which correspond to the conformation with the methine C-H bond eclipsed with the benzene ring and syn or anti with respect to an unsymmetrical phenyl substituent.The third series is much more intense, has a B + C value which is the average of the syn and anti forms, and is consistent with the superposition of spectra of torsionally excited species.
- True, Nancy S.,Farag, Maya, S.,Bohn, Robert K.,MacGregor, Malcolm A.,Radhakrishnan, J.
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Read Online
- Synthesis, photo-sensitive and electrochemical properties of rod-like aromatic aldehyde with azo bridge
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Eight new rod-like liquid crystal molecules composed by a long rigid core of three six-member rings (cyclohexane ring or benzene ring), azo, ester and terminal aldehyde groups have been prepared. These rod-like liquid crystalline molecules were designed to construct new structures to further study photo-isomerization in their mesophases. All the compounds have been characterized based on their basic spectral data, differential scanning calorimeter (DSC) and hot stage polarizing optical microscope (HS-POM). The result showed that all the molecules, even those with the shortest terminal methyl group, have liquid crystalline properties. Their mesophases are nematic within the temperature ranges from 85 to 145°C. They exhibit photo-sensitivities not only in methanol solutions but also in a mesophase when exposed to UV light. The highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) and the differences between the frontier molecular orbitals (Eg) of these compounds were determined by cyclic voltammetry. The effect of even-odd carbon number of the terminal straight alkyl chain on the UV spectral data and the Eg were observed. The difference between the Eg of these compounds are in excellent agreement with the difference of their maximum absorption wavelength in UV spectra.
- Zheng, Minyan,Wei, Yongsheng,Geng, Wei
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Read Online
- Liquid crystal of ethyl and propyl aromatic aldehyde with azo core and photosensitivity in mesophase
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Eight new stable rod-like aromatic aldehyde liquid crystalline molecules with azo bridge have been prepared, in which single or double six-membered carbon ring carboxylic acid mesogenic cores with shorter alkyl chain of ethyl, n-propyl were condensed with hydroxyl azo benzaldehyde. These compounds have been characterized by their spectral data, DSC and HS-POM. These molecules were expected to exhibit liquid crystal phase so that the influence of UV-light on their textures of mesophase could be detected. The results showed that all these target compounds have the temperature range of mesophase between 101 and 145°C. After irradiating under UV-light, they exihibited photo-sensitivity not only in methanol but also in mesophase.
- Wei, Yong-Sheng,Zheng, Min-Yan,Geng, Wei,Wang, Shan,Shang, Yong-Hui
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Read Online
- Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling
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Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.
- Neate, Peter G.N.,Zhang, Bufan,Conforti, Jessica,Brennessel, William W.,Neidig, Michael L.
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supporting information
p. 5958 - 5963
(2021/08/18)
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- Ni-Catalyzed Direct Carboxylation of Aryl C?H Bonds in Benzamides with CO2
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The direct carboxylation of inert aryl C?H bond catalyzed by abundant and cheap nickel is still facing challenge. Herein, we report the Ni-catalyzed direct carboxylation of aryl C?H bonds in benzamides under 1 atm of CO2 to afford various methyl carboxylates or phthalimides, dealing with different post-processing. The reaction displays excellent functional group tolerance and affords moderate to high carboxylation yields under mild conditions. Detail mechanistic studies suggest that a Ni(0)?Ni(II)?Ni(I) catalytic cycle may be involved in this reaction. (Figure presented.).
- Li, Bin,Pei, Chunzhe,Wang, Baiquan,Zong, Jiarui
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supporting information
(2021/12/08)
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- Synthesis and molecular docking studies of some novel antimicrobial benzamides
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Common use of classical antibiotics has caused to the growing emergence of many resistant strains of pathogenic bacteria. Therefore, we aimed to synthesize a number of N-(2-hydroxy-(4 or 5)-nitrophenyl)benzamide derivatives as a new class of antimicrobial compounds. Moreover, our second goal is to predict the interaction between active structures and enzymes (DNA –gyrase and FtsA) in the binding mode. In this study, thirteen N-(2-hydroxy-(4 or 5-nitrophenyl)-substituted-benzamides were synthesized and determined for their antimicrobial activity using the microdilution method. According to this work, none of the compounds showed any activity against Candida albicans and its clinical isolate. Some of the benzamides (4N1, 5N1, 5N2) displayed very significant activity against Staphylococcus aureus and MSSA with 4 μg/ml MIC value, even they were found to be more potent than ceftazidime. 4N1 was also found to be more effective than gentamicin against Enterococcus faecalis clinical isolate. Molecular docking studies revealed that 4N1, 5N1, and 5N2 showed a good interactions with DNA-gyrase. Moreover, 5N1 has interacted with FtsA enzyme in the binding mode, as well. Only compound 5N4 displayed very good activity against Escherichia coli ATCC 25922. These findings showed us that 4N1, 5N1, 5N2, and 5N4 could be lead compounds to discover new antibacterial candidates against multidrug-resistant strains.
- Acar, Cemre,Yal??n, Gozde,Ertan-Bolelli, Tu?ba,Kaynak Onurda?, Fatma,?kten, Suzan,?ener, Funda,Y?ld?z, ?lkay
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- Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters
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We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.
- Lee, Minhan,Jung, Hoimin,Kim, Dongwook,Park, Jung-Woo,Chang, Sukbok
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supporting information
p. 11999 - 12004
(2020/08/06)
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- Base-promoted Lewis acid catalyzed synthesis of quinazoline derivatives
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A one-pot protocol has been developed for the synthesis of quinazolinones from amide-oxazolines with TsCl via a cyclic 1,3-azaoxonium intermediate and 6π electron cyclization in the presence of a Lewis acid and base. The process is operationally simple and has a broad substrate scope. This method provides a unique strategy for the construction of quinazolinones.
- Cui, Xin-Feng,Hu, Fang-Peng,Huang, Guo-Sheng,Lu, Guo-Qiang
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supporting information
p. 4376 - 4380
(2020/10/20)
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- Vinylogous Elimination/C-H Functionalization/Allylation Cascade Reaction of Allenoate Adducts: Synthesis of Ring-Fused Dihydropyridinones
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A palladium-catalyzed cascade reaction of β′-allenoate adducts with aryl/heteroaryl carboxamides through a vinylogous elimination/C-H functionalization/intramolecular allylation reaction sequence has been developed with high Z stereoselectivity. Various ring-fused dihydropyridinones bearing an α,β-unsaturated ester substituent are obtained. It is the first example of application of the allenoate adducts to C-H functionalization annulations as practical precursors of hard-to-get functionalized electron-deficient 1,3-butadienes. Using air as the terminal oxidant also shows a great advantage in environmental friendliness.
- Sun, Manman,Chen, Weida,Wu, Haijian,Xia, Xiangyu,Yang, Jianguo,Wang, Lei,Shen, Guodong,Wang, Zhiming
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supporting information
p. 8313 - 8319
(2020/11/03)
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- Acylated 1 H-1,2,4-Triazol-5-Amines Targeting Human Coagulation Factor XIIa and Thrombin: Conventional and Microscale Synthesis, Anticoagulant Properties, and Mechanism of Action
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We herein report the conventional and microscale parallel synthesis of selective inhibitors of human blood coagulation factor XIIa and thrombin exhibiting a 1,2,4-Triazol-5-Amine scaffold. Structural variations of this scaffold allowed identifying derivative 21i, a potent 29 nM inhibitor of FXIIa, with improved selectivity over other tested serine proteases and also finding compound 21m with 27 nM inhibitory activity toward thrombin. For the first time, acylated 1,2,4-Triazol-5-Amines were proved to have anticoagulant properties and the ability to affect thrombin-And cancer-cell-induced platelet aggregation. Performed mass spectrometric analysis and molecular modeling allowed us to discover previously unknown interactions between the synthesized inhibitors and the active site of FXIIa, which uncovered the mechanistic details of FXIIa inhibition. Synthesized compounds represent a promising starting point for the development of novel antithrombotic drugs or chemical tools for studying the role of FXIIa and thrombin in physiological and pathological processes.
- Korff, Marvin,Imberg, Lukas,Will, Jonas M.,Bückrei?, Nico,Kalinina, Svetlana A.,Wenzel, Benjamin M.,Kastner, Gregor A.,Daniliuc, Constantin G.,Barth, Maximilian,Ovsepyan, Ruzanna A.,Butov, Kirill R.,Humpf, Hans-Ulrich,Lehr, Matthias,Panteleev, Mikhail A.,Poso, Antti,Karst, Uwe,Steinmetzer, Torsten,Bendas, Gerd,Kalinin, Dmitrii V.
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p. 13159 - 13186
(2020/11/13)
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- Identification of Anti-Mycobacterial Biofilm Agents Based on the 2-Aminoimidazole Scaffold
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Tuberculosis (TB) remains a significant global health problem for which new therapeutic options are sorely needed. The ability of the causative agent, Mycobacterium tuberculosis, to reside within host macrophages and form biofilm-like communities contributes to the persistent and drug-tolerant nature of the disease. Compounds that can prevent or reverse the biofilm-like phenotype have the potential to serve alongside TB antibiotics to overcome this tolerance, and decrease treatment duration. Using Mycobacterium smegmatis as a surrogate organism, we report the identification of two new 2-aminoimidazole compounds that inhibit and disperse mycobacterial biofilms, work synergistically with isoniazid and rifampicin to eradicate preformed M. smegmatis biofilms in vitro, are nontoxic toward Galleria mellonella, and exhibit stability in mouse plasma.
- Nguyen, T. Vu,Minrovic, Bradley M.,Melander, Roberta J.,Melander, Christian
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p. 927 - 937
(2019/03/26)
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- Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent
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The palladium-catalyzed electrochemical C-H bromination of benzamide derivatives under divided cells is developed, in which NH4Br serves as a brominating reagent and electrolyte. The protocol avoids the use of chemical oxidants and provides an alternative method for the synthesis of aryl bromides.
- Yang, Qi-Liang,Wang, Xiang-Yang,Wang, Tong-Lin,Yang, Xiang,Liu, Dong,Tong, Xiaofeng,Wu, Xin-Yan,Mei, Tian-Sheng
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supporting information
p. 2645 - 2649
(2019/04/17)
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- Synthesis and bioactivities of diamide derivatives containing a phenazine-1-carboxamide scaffold
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Taking natural product phenazine-1-carboxamide (PCN) as a lead compound, a series of novel phenazine-1-carboxylic acid diamide derivatives were designed and synthesised. Their structures were confirmed by 1H-NMR and HRMS. The bioassays showed that some of the target compounds exhibited promising in vitro fungicidal activities, and exhibited excellent and selective herbicidal activities. Particularly, compounds c, h, o and s displayed root length inhibition activities against barnyard grass with the rate of more than 80%. Compound c exhibited the best activity among all the target compounds against barnyard grass stalk length with the IC50 value of 0.158?mmol/L, and compound o exhibited the best and wide spectrum inhibition against barnyard grass root length and rape in both root length and stalk length herbicidal activities with its IC50 values of 0.067, 0.048 and 0.059?mmol/L respectively. The analysis of preliminary Structure-Activity Relationships provides the theoretical basis for further design of phenazine-1-carboxylic acid.
- Zhu, Xiang,Zhang, Min,Yu, Linhua,Xu, Zhihong,Yang, Dan,Du, Xiaoying,Wu, Qinglai,Li, Junkai
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supporting information
p. 2453 - 2460
(2018/03/29)
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- Asymmetric Palladium-Catalyzed C-H Functionalization Cascade for Synthesis of Chiral 3,4-Dihydroisoquinolones
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A palladium-catalyzed C-H functionalization/intramolecular asymmetric allylation cascade of N-sulfonyl benzamides with 1,3-dienes has been developed. In the presence of a chiral pyridine-oxazoline ligand, this protocol enables the synthesis of chiral 3,4-dihydroisoquinolones in yields of up to 83% with enantioselectivities of up to 96%, using environmentally friendly air as the terminal oxidant.
- Sun, Manman,Wu, Haijian,Xia, Xiangyu,Chen, Weida,Wang, Zhiming,Yang, Jianguo
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p. 12835 - 12847
(2019/11/02)
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- Copper-Mediated Cyanation of Aryl C—H Bond with Removable Bidenate Auxiliary Using Acetonitrile as the Cyano Source
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Copper-mediated cyanation of aryl C—H bond with removable bidenate auxiliary as a directing group has been developed, in which green and cheap acetonitrile is used as the “CN” source. By switching the reaction conditions, the C—H cyanated products and N-Ar-phthalimides can be provided in acceptable yields with high chemoselectivity, respectively. The use of quaternary ammonium salt is essential for cyanation reaction.
- Yu, Zhengwei,Zhang, Saisai,Shen, Zengming
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supporting information
p. 1139 - 1142
(2018/10/15)
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- Lanthanoid complexes supported by retro-Claisen condensation products of β-triketonates
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β-Triketonates have been recently used as chelating ligands for lanthanoid ions, presenting unique structures varying from polynuclear assemblies to polymers. In an effort to overcome low solubility of the complexes of tribenzoylmethane, four β-triketones with higher lipophilicity were synthesised. Complexation reactions were performed for each of these molecules using different alkaline bases in alcoholic media. X-ray diffraction studies suggested that the ligands were undergoing decomposition under the reaction conditions. This is proposed to be caused by in situ retro-Claisen condensation reactions, consistent with two examples that have been reported previously. The lability of the lanthanoid cations in the presence of a varying set of potential ligands gave rise to structures where one, two, or three of the molecules involved in the retro-Claisen condensation reaction were linked to the lanthanoid centres. These results, along with measurements of ligand decomposition in the presence of base alone, suggest the solvent used will modulate the impact of the retro-Claisen condensation in these complexes.
- Abad Galán, Laura,Sobolev, Alexandre N.,Zysman-Colman, Eli,Ogden, Mark I.,Massi, Massimiliano
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p. 17469 - 17478
(2019/01/03)
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- Discovery of N-(3-(5-((3-acrylamido-4-(morpholine-4-carbonyl)phenyl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-(tert-butyl)benzamide (CHMFL-BTK-01) as a highly selective irreversible Bruton's tyrosine kinase (BTK) inhibitor
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Currently there are several irreversible BTK inhibitors targeting Cys481 residue under preclinical or clinical development. However, most of these inhibitors also targeted other kinases such as BMX, JAK3, and EGFR that bear the highly similar active cysteine residues. Through a structure-based drug design approach, we discovered a highly potent (IC50: 7?nM) irreversible BTK inhibitor compound 9 (CHMFL-BTK-01), which displayed a high selectivity profile in KINOMEscan (S score (35)?=?0.00) among 468 kinases/mutants at the concentration of 1?μM. Compound 9 completely abolished BMX, JAK3 and EGFR's activity. Both X-ray crystal structure and cysteine-serine mutation mediated rescue experiment confirmed 9's irreversible binding mode. 9 also potently inhibited BTK Y223 auto-phosphorylation (EC50: 30?nM), arrested cell cycle in G0/G1 phase and induced apoptosis in U2932 and Pfeiffer cells. We believe these features would make 9 a good pharmacological tool to study the BTK related pathology.
- Liang, Qianmao,Chen, Yongfei,Yu, Kailin,Chen, Cheng,Zhang, Shouxiang,Wang, Aoli,Wang, Wei,Wu, Hong,Liu, Xiaochuan,Wang, Beilei,Wang, Li,Hu, Zhenquan,Wang, Wenchao,Ren, Tao,Zhang, Shanchun,Liu, Qingsong,Yun, Cai-Hong,Liu, Jing
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p. 107 - 125
(2017/03/21)
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- Synthesis, structure, and mesomorphism of novel liquid crystalline acrylate monomers and polymers
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A series of novel liquid crystalline monomers (M1-M8) and side chain polymers base polyacrylate backbone were synthesized. The chemical structures were characterized by FT-IR and 1H-NMR spectra. The mesomorphism and thermal behavior was investigated by polarizing optical microscopy, differential scanning calorimetry, and thermogravimetric analysis. The relationships of structure and mesomorphism are discussed in detail. The eight monomers and their corresponding polymers all show enantiotropic nematic phase. With increasing the spacer length or flexibility of the terminal group, the melting temperature (Tm) and isotropic temperature (Ti) of the corresponding monomers and polymers all decreased. However, with increasing the rigidity of the mesogenic core, Tm and Ti of the corresponding monomers and polymers all increased. TGA showed that all the polymers obtained in this study had excellent thermal stability.
- Xu, Xiao-Xu,Chao, Chun-Ying,Yao, Xi-Jing
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- Synthesis, structure and biological activities of novel triazole compounds containing Ester Group
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Novel triazole compounds containing ester group were synthesized. Their structure were confirmed by means of IR, 1H NMR and elemental analysis. The single crystal structure of compound (1H-1,2,4-triazol-1-yl)methyl 3-(2,4-dichlorophenyl)propanoate (compound 3c) was determined via X-ray diffraction. It crystallizes in a monoclinic system with space group P2(1)/c, a = 1.0814(2) nm, b = 0.64514(13) nm, c = 1.8698(4) nm, β = 101.05(3)°, Z = 4, V = 1.2802(5) nm3, Dc = 1.557 Mg/m3, μ = 0.508 mm-1, F(000) = 616 and final R1 = 0.0700. Intermolecular hydrogen-bond and φ-φ stacking interactions exit in the lattice, facilitating the stabilization of crystal structure. The results of the biological test show that these compounds have some fungicidal activity.
- Yang, Shuang-Hua,Zhai, Zhi-Wei,Zhang, Shao-Wen
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p. 883 - 886
(2014/06/09)
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- Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors
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Human African trypanosomiasis (HAT) is one of the most neglected diseases in the tropic regions, which is fatal if not treated in time. There is an urgent need for new therapeutics, especially those in new chemical classes. Leucyl-tRNA synthetase (LeuRS) has been paid much attention as a recently clinically validated antimicrobial target. Our group has previously reported T. brucei LeuRS (TbLeuRS) inhibitors, including benzoxaboroles targeting the editing site and pyrrolinones targeting the synthetic site. Here we report the discovery of N-(4-sulfamoylphenyl)thioureas as a new class of TbLeuRS inhibitors. The R1 and R2 groups, reminiscent of the leucyl and adenyl regions of aa-AMP and aa-AMS, were optimized to result in a significant 13-fold increase of inhibitory activity (compound 19, IC 50 = 13.7 μM). Aided by ligand-protein docking, the 1,3-substitution at the central phenyl ring was predicted and proved to give significantly improved activity (59, IC50 = 1.1 μM). This work provided a new scaffold for the exploration of novel inhibitors against TbLeuRS, which may become potential therapeutics for the treatment of HAT.
- Zhang, Fenglong,Du, Jin,Wang, Qing,Hu, Qinghua,Zhang, Jiong,Ding, Dazhong,Zhao, Yaxue,Yang, Fei,Wang, Enduo,Zhou, Huchen
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p. 5310 - 5324
(2013/08/23)
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- Synthesis of novel 2-[4-(4-substitutedbenzamido/phenylacetamido) phenyl]benzothiazoles as antimicrobial agents
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A new series of 2-[4-(4-substitutedbenzamido/ phenylacetamido)phenyl] benzothiazole derivatives (6a-k) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Escherichia coli with their drug-resistant isolates and a yeast Candida albicans. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at minimum inhibitory concentration (MIC) values between 100 and 6.25 lg/ml. Compounds 6d and 6k exhibited significant antibacterial activity showing 6.25 lg/ml MIC values against drugresistant S. aureus and P. aeruginosa isolates, respectively. Springer Science+Business Media, LLC 2011.
- Bolelli, Kayhan,Yalcin, Ismail,Ertan-Bolelli, Tugba,?zgen, Selda,Kaynak-Onurdag, Fatma,Yildiz, Ilkay,Aki, Esin
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p. 3818 - 3825
(2013/02/23)
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- SMALL MOLECULE CHOLINE KINASE INHIBITORS, SCREENING ASSAYS, AND METHODS FOR SAFE AND EFFECTIVE TREATMENT OF NEOPLASTIC DISORDERS
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Small molecule choline kinase inhibitors, pharmaceutical compositions thereof, and screening methods for identifying and evaluating choline kinase inhibitors are provided. Safe and effective methods for treating subjects suffering from a disorder or disease characterized by neoplastic cell proliferation employing the choline kinase inhibitors are also provided
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Page/Page column 17; 18; 19
(2011/09/20)
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- (1 S)-1,5-anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio- d -glucitol (TS-071) is a potent, selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for type 2 diabetes treatment
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Derivatives of a novel scaffold, C-phenyl 1-thio-d-glucitol, were prepared and evaluated for sodium-dependent glucose cotransporter (SGLT) 2 and SGLT1 inhibition activities. Optimization of substituents on the aromatic rings afforded five compounds with potent and selective SGLT2 inhibition activities. The compounds were evaluated for in vitro human metabolic stability, human serum protein binding (SPB), and Caco-2 permeability. Of them, (1S)-1,5-anhydro-1-[5- (4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-d-glucitol (3p) exhibited potent SGLT2 inhibition activity (IC50 = 2.26 nM), with 1650-fold selectivity over SGLT1. Compound 3p showed good metabolic stability toward cryo-preserved human hepatic clearance, lower SPB, and moderate Caco-2 permeability. Since 3p should have acceptable human pharmacokinetics (PK) properties, it could be a clinical candidate for treating type 2 diabetes. We observed that compound 3p exhibits a blood glucose lowering effect, excellent urinary glucose excretion properties, and promising PK profiles in animals. Phase II clinical trials of 3p (TS-071) are currently ongoing.
- Kakinuma, Hiroyuki,Oi, Takahiro,Hashimoto-Tsuchiya, Yuko,Arai, Masayuki,Kawakita, Yasunori,Fukasawa, Yoshiki,Iida, Izumi,Hagima, Naoko,Takeuchi, Hiroyuki,Chino, Yukihiro,Asami, Jun,Okumura-Kitajima, Lisa,Io, Fusayo,Yamamoto, Daisuke,Miyata, Noriyuki,Takahashi, Teisuke,Uchida, Saeko,Yamamoto, Koji
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experimental part
p. 3247 - 3261
(2010/10/02)
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- FT-IR, FT-Raman, SERS spectra and computational calculations of 4-ethyl-N-(2'-hydroxy-5'-nitrophenyl) benzamide
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Fourier transform infrared (FT-IR) and FT-Raman spectra of 4-ethyl-N-(2'hydroxy-5'-nitrophenyl) benzamide were recorded and analyzed. A surface-enhanced Raman scattering (SERS) spectrum was recorded in silver colloid. The vibrational wavenumbers and corresponding vibrational assignments were examined theoretically using the Gaussian03 set of quantum chemistry codes. The red shift of the NH stretching wavenumber in the infrared spectrum from the computational wavenumber indicates the weakening of the NH bond resulting in proton transfer to the neighboring oxygen atom. The simultaneous IR and Raman activation of the C O stretching mode gives the charge transfer interaction through a π-conjugated path. The presence of methyl modes in the SERS spectrum indicates the nearness of the methyl group to the metal surface, which affects the orientation and metal molecule interaction. The first hyperpolarizability and predicted infrared intensities are reported. The calculated first hyperpolarizability is comparable with the reported values of similar derivatives and is an attractive subject for future studies of nonlinear optics. Optimized geometrical parameters of the title compound are in agreement with reported structures.
- Panicker, C. Yohannan,Varghese, Hema Tresa,Ushakumari,Ertan, Tugba,Yildiz, Ilkay,Granadeiro, Carlos M.,Nogueira, Helena I. S.,Shyma Mary
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experimental part
p. 381 - 390
(2011/12/02)
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- GLUCOPYRANOSYL-SUBSTITUTED BENZYL-BENZONITRILE DERIVATIVES, MEDICAMENTS CONTAINING SUCH COMPOUNDS, THEIR USE AND PROCESS FOR THEIR MANUFACTURE
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Glucopyranosyl-substituted benzyl-benzonitrile derivatives of general formula (I) as defined according to claim 1, including the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
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Page/Page column 40-41
(2008/12/05)
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- BENZYLIC GLYCOSIDE DERIVATIVES AND METHODS OF USE
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Provided are compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The invention also provides pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions which are affected by SGLT inhibition.
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Page/Page column 28
(2008/12/07)
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- Synthesis and biological evaluation of new N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamides and phenylacetamides as antimicrobial agents
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A new series of N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamide and phenylacetamide derivatives (1a-1n, 2a-2n) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, and their drug-resistant isolate. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 500 and 1.95 μg/ml. Benzamide derivative 1d exhibited the greatest activity with MIC values of 1.95, 3.9, and 7.8 μg/ml against drug-resistant B. subtilis, B. subtilis, and S. aureus, respectively.
- Ertan, Tugba,Yildiz, Ilkay,Ozkan, Semiha,Temiz-Arpaci, Ozlem,Kaynak, Fatma,Yalcin, Ismail,Aki-Sener, Esin,Abbasoglu, Ufuk
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p. 2032 - 2044
(2007/10/03)
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- Preparation of new substituted bis(benzoyl) peroxides under aqueous conditions in the presence of stearyltrimethylammonium chloride
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A series of new substituted bis(benzoyl) peroxides has been synthesised from their corresponding acid chlorides in high yield. The reactions were carried out in aqueous sodium peroxide solution and butanone in the presence of 0.5% stearyltrimethylammonium chloride (STAC) at a temperature below 15°C. STAC improved the purity, and the fast addition improved the yield of the peroxides. Mass spectral analysis of substituted bis(benzoyl) peroxides using EI has been carried out for accurate mass determinations. Springer-Verlag 2003.
- Moorhoff, Cornelis M.,Braybrook, Carl
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p. 397 - 405
(2007/10/03)
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- Synthesis and antimicrobial activity of new 2-[p-substituted-benzyl]-5- [substituted-carbonyl-amino]benzoxazoles
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A series of 23 new 2-[p-substituted-benzyl]-5-[p-substituted-phenyl/benzyl- carbonylamino]benzoxazole derivatives has been synthesized by reacting 5-amino-2-[p-substituted-benzyl]benzoxazoles with the appropriate carboxylic acid chlorides. The structures of the synthesized compounds were confirmed by IR and 1H-NMR spectral data. Antimicrobial activities of the compounds were investigated using the twofold serial dilution technique against two gram-positive and two gram-negative bacteria and three Candida species in comparison with standard drugs. Microbiological results indicated that the newly synthesized 2-[p-substituted-benzyl]-5-[p-substituted-phenyl/benzyl- carbonylamino]benzoxazole derivatives (3-25) possessed a broad spectrum of activity, showing MIC values of 6.25-200 μg/mL against the gram-positive and gram-negative microorganisms tested. Moreover, they showed significant antifungal activity with MIC values of 3.12-100 μg/mL against the Candida species tested. Especially, with a MIC value of 3.12 μg/mL, 2-benzyl-5-[p-bromobenzyl-carbonylamino]benzoxazole 9 displayed the same activity against C. glabrata as the standard drug myconazol.
- Yildiz-Orena, Ilkay,Tekiner-Gulbas, Betul,Yalcin, Ismail,Temiz-Arpaci, Ozlem,Aki-Sener, Esin,Altanlar, Nurten
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p. 402 - 410
(2007/10/03)
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- Infrared and Nuclear Magnetic Resonance Properties of Benzoyl Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
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Benzophenones, 2-benzoylthiophenes, 2-benzoylpyrroles, and 2-benzoylfurans, which have substituents at m- and p-positions of the benzoyl ring were prepared and their ir and nmr spectra were obtained in 0.1 M chloroform-d solution. The chemical shift values of each series were plotted against the Hammett substituent parameters to give good correlation, with the exception of the ortho-Hs and -Cs. The slopes as well as the differences in chemical shift gave sets of meaningful values for the indices of aromaticy.
- Jeon, Kyu Ok,Jun, Jung Ho,Yu, Ji Sook,Lee, Chang Kiu
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p. 763 - 771
(2007/10/03)
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- O-glucosylated benzamide SGLT2 inhibitors and method
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SGLT2 inhibiting compounds are provided having the formula wherein n is 0, 1 or 2; A is or heteroaryl which may contain 1 to 4 heteroatoms in the ring which may be selected from N, O, S, SO, and/or SO2, bearing substituents R3 and R4; and R1 to R4 are as defined herein. A method is also provided for treating diabetes and related diseases employing an SGLT2 inhibiting amount of the above compound alone or in combination with one, two or more other antidiabetic agents and/or one, two or more hypolipidemic agents.
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- Synthesis and microbiological activity of some novel 5-benzamido- and 5- phenylacetamido- substituted 2-phenylbenzoxazole derivatives
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The synthesis and microbiological activity of a new series of 5- benzamido- and 5-phenylacetamidosubstituted-2-phenylbenzoxazole derivatives (1-26) were described. The in vitro microbiological activity of the compounds was determined against Gram-positive, Gram-negative bacteria and the yeast Candida albicans in comparison with standard drugs. Microbiological results indicated that the synthesized compounds possessed a broad spectrum of activity against the tested microorganisms. The compounds 1, 21, 25 showed higher activity than tetracycline and streptomycin against Pseudomonas aeruginosa. (C) 2000 Elsevier Science S.A.
- Sener, Esin Aki,Temiz Arpaci, Oezlem,Yalcin, Ismail,Altanlar, Nurten
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p. 397 - 405
(2007/10/03)
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- Synthesis of Derivatives of 4-Ethylbenzoic and 4-Ethylcyclohexanecarboxylic Acids
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A procedure has been developed for preparation of derivatives of 4-ethylbenzoic and 4-ethycyclohexanecarboxylic acids via liquid-phase catalytic oxidation and hydrogenation. From 4-ethylbenzoyl chloride the corresponding esters and N-arylamides have been synthesized, and from 4-ethylcyclohexanecarbonyl chloride, the corresponding N-arylamides.
- Betnev,Obukhova,Budanov,Danilova,Obukhov
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- Molting hormonal and larvicidal activities of aliphatic acyl analogs of dibenzoylhydrazine insecticides
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Dibenzoylhydrazines are the nonsteroidal ecdysone agonists. Using comparative molecular field analysis, we previously found that the alkyl side chain of 20-hydroxyecdysone (20E) is three-dimensionally superposable with one of their two aryl moieties. To identify the aryl moiety that is better superposable on the alkyl chain, we synthesized compounds in which one of the two aryl groups of tebufenozide (N-t-butyl-N-3,5-dimethylbenzoyl-N'-4- ethylbenzoylhydrazine) is replaced by alkyl groups such as C4H9, C5H11, and C6H13. The molting hormonal activity of these compounds was measured using cultured integuments prepared from rice stem borers, Chilo suppressalis Walker, in terms of stimulation of incorporation of N:acetyl- [14C]glucosamine. N-t-Butyl-N-3,5-dimethylbenzoyl-N'-acylhydrazines with a hexanoyl or heptanoyl group were about 20-fold higher than that of 20E, whereas N-acyl-N-t-butyl-N'-4-ethylbenzoylhydrazines with a hexanoyl or heptanoyl group were much weaker than 20E. Their larvicidal activity was also measured against rice stem borers. The former series of compounds were much more active than the other series as well as 20E. Thus, the benzoyl moiety of dibenzoylhydrazines, which is bound to the secondary nitrogen atom (-NH-), is replaceable by aliphatic acyl groups without, greatly, affecting the biological activities.
- Shimizu, Bun-Ichi,Nakagawa, Yoshiaki,Hattori, Kazunari,Nishimura, Keiichiro,Kurihara, Norio,Ueno, Tamio
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p. 638 - 642
(2007/10/03)
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- Synthesis and biological evaluation of a series of substituted benzo[a]phenanthridines as agonists at D1 and D2 dopamine receptors
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Dihydrexidine [4; (±)-trans- 10, 11-dihydroxy-5,6,6a,7,8,12b- hexahydrobenzo[a]phenanthridine (DHX)], the first high-affinity full D1 agonist, also is known to have significant D2 activity. The present work reports the synthesis and pharmacological activity of a series of analogs substituted in the pendent phenyl ring (i.e., 2-, 3-, or 4-position). (±)- trans-2-Methyl-10,11-dihydroxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine (5) was a high-affinity D1 agonist, having approximately 4-fold greater D1 vs D2 selectivity than DHX itself. All of the analogs containing a methyl or ethyl (but not a phenyl) substituent at the 2-, 8-, or 4-position had a pharmacological profile similar to that of the lead compound DHX (4). Each analog was found to be a high-affinity full agonist with moderate selectivity for the D1 receptor. It is apparent from these results that the D1 receptor can tolerate small substituents at the 2-, 3-, and 4-positions of the pendent phenyl ring. On the basis of earlier studies showing that N-alkylation increases D2 selectivity, the 3-methyl N-n-propyl and 4-methyl N-n-propyl compounds 11 and 18 were synthesized. While these analogs exhibited much higher affinity for the D2 receptor, surprisingly 4-methyl-N-propyl-DHX (13) exhibited high affinity for both the D1 and D2 receptors. It was subsequently established that this compound is a selective D3 ligand (110- fold selectivity for the D3 over D2 receptor). The results from these studies demonstrate that several of the hexahydrobenzo[a]phenanthridine derivatives are agonists with high intrinsic activity that may serve as powerful tools to explore the structural features that determine affinity and selectivity (relative to the D2 receptor) of drugs for D1 receptors.
- Knoerzer,Watts,Nichols,Mailman
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p. 3062 - 3070
(2007/10/03)
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- Restudy of the Old Poly-2,5-di(benzoyloxy)styrene as a New Liquid Crystal Polymer
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The 40 year old polymer, poly-2,5-di(benzoyloxy)styrene, has been restudied from the view point of the "mesogen-jacketed liquid crystal polymer".This old polymer was synthesized in 1952 as a precursor of an electron exchange polymer and is now found to be thermotropically liquid crystalline, from which the characteristic banded texture of rigid and semi-rigid liquid crystal polymers may be obtained.The monomer of this polymer, 2,5-di(benzoyloxy)styrene, was then also not realized as liquid crystalline, is now found to be liquid crystalline forming too.This finding offers probably the first example of liquid crystal rigid rod-like molecules with lateral but without terminal substitutions.The synthesis and primary characterization of a series of the closely related polymers poly-2,5-bisstyrenes are also reported. - Keywords: mesogen jacketed liquid crystal polymers, rigid side chain liquid crystal polymers, liquid crystal monomers, liquid crystal polymers, 2,5-bisstyrene, 2,5-bisstyrene, 2,5-bisstyrene, 2,5-di(benzoyloxy)styrene, poly-2,5-di(benzoyloxy)styrene
- Zhou, Qi-Feng,Wan, Xinhua,Zhu, Xin-Long,Zhang, Fei,Feng, Xinde
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p. 107 - 118
(2007/10/02)
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- Synthesis, gastrointestinal prokinetic activity and structure-activity relationships of novel N-[[2-(dialkylamino)ethoxy]benzyl]benzamide derivatives
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Novel N-[[2-(dialkylamino)ethoxy]benzyl]benzamide derivatives (II-1-51), derived from the structural modification of metoclopramide (1), were synthesized and examined for their pharmacological activities. Among them, N-[4-[2-(dimethylamino)ethoxy]benzyl]-3,4-dimethoxybenzamide (II-34) which exhibited well balanced gastrointestinal prokinetic and antiemetic activities was selected as a new type of gastrointestinal prokinetic agent.
- Sakaguchi,Nishino,Ogawa,Iwanaga,Yasuda,Kato,Ito
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p. 202 - 211
(2007/10/02)
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- A comparison of electron spin resonance α- and β-hyperfine coupling constants in para-substituted α-phenethyl radicals
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The linear relationship between the electron spin resonance hyperfine coupling constants (hfc) of the α- and β-hydrogens of para-substituted α-phenethyl radicals provides experimental evidence that the magnitude of both the α- and β-hfc is determined largely by the extent of spin delocalization in these benzylic systems.The ?α. scale, developed using substituted radicals, is shown to apply to phenethyl radicals as well.
- Arnold, Donald R.,Nicholas, A. Martin De P.,Young, Kent M.
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p. 769 - 772
(2007/10/02)
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- Therapeutically useful benzylidene derivatives
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Benzylidene derivatives of the formula: STR1 wherein n is 3, R represents an amino or hydroxy radical, or a group --OM in which M is an alkali metal, X1 and X2 are both Cl, and X3 is hydrogen are new compounds possessing useful pharmacological properties; they are, more particularly, useful in the treatment of various diseases of the central nervous system.
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