- N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound
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The invention belongs to the technical field of medicines, relates to a compound with antitumor activity and a specific chemical structure, and in particular relates to an N-((6, 7-dimethoxyquinoline-4-yl) oxy) methyl)-N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound and a preparation method and an application thereof. The structural general formula of the compound is shown in the specification, wherein an R group is mono-substituted or double-substituted phenyl, fluorophenyl, chlorphenyl, bromophenyl, benzyl, benzyloxy, benzene nitro or trifluoromethyl substituted at 2-position, 3-position or 4-position. Pharmacological studies show that the compound provided by the invention has a relatively remarkable proliferation inhibition effect on HER-2 positive breast cancer cells SK-Br-3, the effect is obviously superior to that of HER-2 negative breast cancer cells MCF-7, the compound can be used for preparing antitumor drugs, and a new way is opened up for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.
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-
Paragraph 0051; 0057; 0069-0071
(2021/06/09)
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- Synthesis and Biological Evaluation of Oxadiazole Clubbed Thiadiazole Derivatives as Antimicrobial Agents
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A series of 1,3,4-oxadiazole clubbed 1,3,4-thiadiazole derivatives were synthesized and assessed in vitro for their activity as antimicrobial agents. The target compounds 2-(5-(substituted aryl)-1, 3, 4-oxadiazol-2-ylthio)-N-(5-(substituted aryl)-1, 3, 4-thiadiazol-2-yl) acetamides (5a-5s) were synthesized using a basic condensation reaction between 5-(substituted aryl)-1,3,4-oxadiazole-2-thiol and 2-chloro-N-(5-(substituted aryl)-1,3,4-thiadiazol-2-yl)acetamide in presence of K2CO3 as a scavenging agent and acetone as reaction solvent. The titled compounds synthesized here, exhibited excellent to moderate antimicrobial activity against a broad panel of antibacterial strains of Gram-positive and Gram-negative bacteria and fungi.
- Begari, Eeshwaraiah,Dave, Alpa Y.,Joshi, Deepkumar S.,Parmar, Kokila A.
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p. 273 - 280
(2021/08/03)
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- Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones
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The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.
- Wei, Zeyang,Zhang, Qi,Tang, Meng,Zhang, Siyu,Zhang, Qian
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supporting information
p. 4436 - 4440
(2021/05/26)
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- Synthesis, docking, and biological evaluation of thiazolidinone derivatives against hepatitis C virus genotype 4a
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Hepatitis C virus (HCV) genotype 4a (GT4a) is prevalent in Egypt. It did not gain the necessary scientific focus despite its high resistance. Since the crystal structure NS5B (RNA-dependent RNA polymerase) of HCV GT4a has not been resolved until now, homology modeling was conducted to build and validate the 3D model of the enzyme. Ligand binding sites including the allosteric thumb II pocket were detected and used in lead optimization. Sixty new 4-thiazolidinone derivatives have been virtually designed and docked into thumb II site of HCV NS5B GT4a using rigid docking approach. Eighteen compounds (7a–r) that show good docking scores were synthesized and tested in vitro against NS5B GT4a. Compounds 7b and 7n showed the best inhibitory activity (IC50 = 0.338 and 0.342 μM, respectively). Compounds 7a, 7b, 7c, 7d, 7k, 7n, 7q, and 7r that have IC50 values less than 2 μM were assessed for cellular anti-HCV GT4a activity using human hepatoma cell line (Huh 7.5). The percentages of viral growth inhibition are between 79.67 and 94.77%. Compound 7b is the most active in the in vitro and cellular assays and could be considered a potential new lead for future anti-HCV studies. [Figure not available: see fulltext.]
- Al-Behery, Ahmed S.,Elberembally, Kamel M.,Eldawy, Mohammed A.
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p. 1151 - 1165
(2021/04/05)
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- Synthesis of indole-tethered [1,3,4]thiadiazolo and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids as anti-pancreatic cancer agents
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New indole-tethered [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (8a-j) and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids (9a-e) were synthesized using [4+2] cycloaddition reactions of functionalized 1,3-diazabuta-1,3-dienes with indole-ketenes. All molecul
- Gummidi, Lalitha,Kerru, Nagaraju,Awolade, Paul,Raza, Asif,Sharma, Arun K.,Singh, Parvesh
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- Novel fatty acid-thiadiazole derivatives as potential antimycobacterial agents
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The discovery of antibiotics around the middle twentieth century led to a decrease in the interest in antimycobacterial fatty acids. In order to re-establish the importance of naturally abundant fatty acid, a series of fatty acid-thiadiazole derivatives were designed and synthesized based on molecular hybridization approach. In vitro antimycobacterial potential was established by a screening of synthesized compounds against Mycobacterium tuberculosis H37Rv strain. Among them, compounds 5a, 5d, 5h, and 5j were the most active, with compound 5j exhibiting minimum inhibitory concentration of 2.34?μg/ml against M.tb H37Rv. Additionally, the compounds were docked to determine the probable binding interactions and understand the mechanism of action of most active molecules on enoyl-acyl carrier protein reductases (InhA), which is involved in the mycobacterium fatty acid biosynthetic pathway.
- Mali, Jaishree K.,Sutar, Yogesh B.,Pahelkar, Akshata R.,Verma, Preeti M.,Telvekar, Vikas N.
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p. 174 - 181
(2019/11/03)
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- Synthesis of (1,3,4-thiadiazol-2-yl)-acrylamide derivatives as potential antitumor agents against acute leukemia cells
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A lead compound with the (1,3,4-thiadiazol-2-yl)-acrylamide scaffold was discovered to have significant cytotoxicity on several tumor cell lines in an in-house cell-based screening. A total of 60 derivative compounds were then synthesized and tested in a CCK-8 cell viability assay. Some of them exhibited improved cytotoxic activities. The most potent compounds had IC50 values of 1–5 μM on two acute leukemia tumor cell lines, i.e. RS4;11 and HL-60. Flow cytometry analysis of several active compounds and detection of caspase activation indicated that they induced caspase-dependent apoptosis. It was also encouraging to observe that these compounds did not have obvious cytotoxicity on normal cells, i.e. IC50 > 50 μM on HEK-293T cells. Although the molecular targets of this class of compound are yet to be revealed, our current results suggest that this class of compound represents a new possibility for developing drug candidates against acute leukemia.
- An, Ran,Guo, Chun,Li, Qing,Li, Yan,Wang, Renxiao,Xu, Yaochun,Zhou, Mi
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supporting information
(2020/03/25)
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- Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies
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A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole am
- Jakovljevi?, Katarina,Joksovi?, Milan D.,Botta, Bruno,Jovanovi?, Ljiljana S.,Avdovi?, Edina,Markovi?, Zoran,Mihailovi?, Vladimir,Andri?, Marijana,Trifunovi?, Sne?ana,Markovi?, Violeta
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p. 585 - 598
(2019/07/05)
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- Intrabacterial Metabolism Obscures the Successful Prediction of an InhA Inhibitor of Mycobacterium tuberculosis
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Tuberculosis, caused by Mycobacterium tuberculosis (M. tuberculosis), kills 1.6 million people annually. To bridge the gap between structure- A nd cell-based drug discovery strategies, we are pioneering a computer-aided discovery paradigm that merges stru
- Wang, Xin,Perryman, Alexander L.,Li, Shao-Gang,Paget, Steve D.,Stratton, Thomas P.,Lemenze, Alex,Olson, Arthur J.,Ekins, Sean,Kumar, Pradeep,Freundlich, Joel S.
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p. 2148 - 2163
(2019/11/19)
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- Design, synthesis and pharmacological evaluation of carboxamide and carbothioamide derivatives of 1,3,4-thiadiazole as the inhibitors of acetylcholinesterase and oxipiperazine)ative stress for the management of cognitive debility
-
Acetylcholinesterase has been a promising target for the development of putative therapeutics against cognitive decline. The deleterious effect of oxidative stress on the learning and memory paradigms of an individual has also been well documented. In vie
- Kulshreshtha, Akanksha,Piplani, Poonam
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p. 1800 - 1821
(2018/06/18)
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- Synthesis of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold as insecticidal/acaricidal agents
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In continuation of our program aimed at the development of natural product-based pesticidal agents, a series of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold were prepared, and their insecticidal and acaricidal activities were evaluated against Mythimna separata and Tetranychus cinnabarinus. Some compounds exhibited potent insecticidal and acaricidal activities. It suggested that R1 as a nitro group and R2 as a fluorine atom, were important for the insecticidal activity; R1 as the electron-donating groups and R2 as the methyl group, were necessary for the acaricidal activity.
- Lv, Min,Liu, Guangci,Jia, Minghong,Xu, Hui
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-
- Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents
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A series of 5-substituted-1,3,4-thiadiazole-based fluoroquinolone derivatives were designed as potential antibacterial and anticancer agents using a molecular hybridization approach. The target compounds 16–25 were synthesized by reacting the correspondin
- Demirci, Asl?,Karayel, Kaan G?k?e,Tatar, Esra,Okullu, Sinem ?KTEM,Unübol, Nihan,Ta?li, Pakize Neslihan,Kocag?z, Zühtü Tan?l,Sahin, Fikrettin,Kü?ükgüzel, Ilkay
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p. 839 - 858
(2018/06/07)
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- PhI-Catalyzed Intramolecular Oxidative Coupling Toward Synthesis of 2-Amino-1,3,4-Thiadizoles
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A highly efficient method for the synthesis of thiadiazole derivatives via intramolecular oxidative coupling of thiosemicarbazide, using the in situ generated hypervalent iodine(III) reagents is developed. The protocol can be carried out smoothly and provides a variety of thiadiazole derivatives in moderate to excellent yields. Graphical Abstract: A highly efficient method for the synthesis of thiadiazole derivatives via PhI-catalyzed intramolecular oxidative coupling of thiosemicarbazide has been developed.
- Han, Yingzhi,Sun, Yadong,Abdukader, Ablimit,Liu, Bifu,Wang, Duozhi
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p. 3486 - 3491
(2018/09/27)
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- Metal-free synthesis of 2-aminothiadiazoles via TBHP-Mediated oxidative C-S bond formation
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An efficient one-pot synthesis of 2-amino-1,3,4-thiadiazoles from easily available aldehydes and thiosemicarbazide using TBHP as an oxidant has been described. Notably, these reactions were carried out at room temperature using ethanol as solvent. This is the first example for one-pot synthesis of 2-amino-1,3,4-thiadiazole derivatives from aldehydes. This new synthetic methodology provides a simple procedure utilizing a safer oxidizing system that affords the target products in mild reaction condition with satisfactory yields and wide substrate scope.
- Hatvate, Navnath T.,Ghodse, Shrikant M.,Telvekar, Vikas N.
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supporting information
p. 285 - 290
(2018/02/09)
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- Cyclization–oxidation of Benzylidenehydrazinecarbothioamides by FeCl3.6H2O or ZnCl2.6H2O Catalysts and Synthesis of New 1,3,4-Thiadiazolo-[3,2- α]Pyrimidines
-
We report new method for preparation of 2-amino-5-aryl-1,3,4-thiadiazoles by reaction of arylaldehyde with thiosemicarbazide and in the next step via cyclization of 2-aryl hydrazinecarbothioamide in the presence of ZnCl2.6H2O or FeCl3.6H2O. Also, in this research, new substituted 1,3,4-thiadiazolo-[3,2-α]pyrimidines were synthesized by the reaction of 2-amino-5-aryl-1,3,4-thiadiazoles derivatives with DMAD or DEAD in the presence of K2CO3 under reflux conditions. The FT-IR, 1H-NMR, 13C-NMR, elemental analysis and single- crystal X-ray analysis confirm the structures of the products.
- Darehkordi, Ali,Zarezadeh Abarqouei, Behnam,Rahmani, Fariba
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p. 1872 - 1879
(2017/05/29)
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- Synthesis and evaluation of the trypanocidal activity of a series of 1,3,4-thiadiazoles derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones
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In this study, we synthesized a series of 1,3,4-thiadiazole derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones (2a–k). We also determined the cytotoxicity in LLCMK2 cells and the activity against epimastigote and trypomastigote forms
- Martins, Solange C.,Desoti, Vania C.,Lazarin-Bidóia, Danielle,Vandresen, Fábio,da Silva, Cleuza C.,Ueda-Nakamura, Tania,Silva, Sueli de O.,Nakamura, Celso V.
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p. 1193 - 1203
(2016/07/06)
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- Synthesis and biological evaluation of new imidazo[2,1-b][1,3,4]thiadiazole-benzimidazole derivatives
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In this report, we describe the synthesis and biological evaluation of a new series of 2-(imidazo[2,1-b][1,3,4]thiadiazol-5-yl)-1H-benzimidazole derivatives (5a-ac). The molecules were analyzed by 1H NMR, 13C NMR, mass spectral and elemental data. The structure of one of the pre-final compounds, 6-(4-methoxyphenyl)-2-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde (4d) and that of a target compound, 2-[2-methyl-6-(4-methyl phenyl) imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-1H-benzimidazole (5aa) were confirmed by single crystal XRD studies. All the target compounds were screened for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Rv strain. Seven (5c, 5d, 5l, 5p, 5r, 5z and 5aa) out of twenty nine compounds showed potent anti-tubercular activity with a MIC of 3.125 μg/mL. A p-substituted phenyl group (p-tolyl or p-chlorophenyl) in the imidazo[2,1-b][1,3,4]thiadiazole ring and/or a chloro group in the benzimidazole ring enhance anti-tuberculosis activity whereas a nitro group in the benzimidazole ring reduces the activity. In the antibacterial screening, compounds 5i, 5w and 5ac showed promising activity against the tested bacterial strains. Further, antifungal and antioxidant activities of these molecules were also investigated. In the cytotoxicity study, the active antitubercular compounds exhibited very low toxicity against a normal cell line.
- Ramprasad, Jurupula,Nayak, Nagabhushana,Dalimba, Udayakumar,Yogeeswari, Perumal,Sriram, Dharmarajan,Peethambar,Achur, Rajeshwara,Kumar, H. S. Santosh
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-
- Synthesis and biological activity of acylthiourea derivatives contain 1,2,3-thiadiazole and 1,3,4-thiadiazole
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In order to investigate the biological activity of novel thiourea compounds, some novel 1,2,3-thiadiazole derivatives containing 1,3,4-thiadiazole were synthesized under phase transfer catalyzed condition(PEG-600)by multi-step reactions. The chemical structures of all compounds were established by 1H NMR, FTIR, MS, and elemental analysis, and some of these compounds were investigated for fungicidal activity and plant growth regulatory activity. The bioassay results indicated that some of these compound exhibited moderate activities.
- Yang, Ming-Yan,Zhao, Wen,Sun, Zhao-Hui,Tan, Cheng-Xia,Weng, Jian-Quan,Liu, Xing-Hai
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p. 314 - 318
(2015/04/14)
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- Novel imidazo[2,1-b]-1,3,4-thiadiazoles as promising antifungal agents against clinical isolate of Cryptococcus neoformans
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We herein report the synthesis and in vitro antimicrobial evaluation of twenty five novel hybrid derivatives of imidazo [2,1-b]-1,3,4-thiadiazole containing chalcones (5a-o) and Schiff bases (6a-j) against three fungal strains (Candida albicans, Cryptococ
- Karpoormath, Rajshekhar,Palkar, Mahesh B.,Patel, Harun M.,Rane, Rajesh A.,Shaikh, Mahamadhanif S.,Kajee, Afsana,Mlisana, Koleka P.
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p. 514 - 525
(2015/04/14)
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- Molecular sieves promoted, ultrasound-mediated synthesis, biological evaluation and docking study of 3-(5-substituted-1,3,4-thiadiazol-2-ylimino)indolin-2-ones as a potential anticonvulsant agents
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In this work, the combined use of ultrasonic energy and molecular sieves was investigated for synthesis of 3-(5-substituted-1,3,4-thiadiazol-2-ylimino)indolin-2-one derivatives 5(a-j). The equimolar quantities of 5-substituted-1,3,4-thiadiazol-2-amine and
- Nikalje, Anna Pratima G.,Shaikh, Sameer I.,Kalam Khan, Firoz A.,Shaikh, Shoaib,Sangshetti, Jaiprakash N.
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p. 4058 - 4069
(2015/11/02)
-
- Synthesis and anti-inflammatory activity of some new thiadiazole linked pyrazole benzene sulphonamides as cyclooxygenase inhibitors
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A new series of thiadiazole linked pyrazole benzenesulfonamide derivatives were synthesized by the condensation of aldehydic pyrazole with aryl substituted thiadiazole amine followed by Schiff base reaction. The synthesized compounds (6a-o) were characterized by IR, NMR, and Mass spectral data, further evaluated their in-vivo anti-inflammatory, analgesic and invitro COX-II inhibition assay. The compounds 6b and 6m showed most significant in-vivo antiinflammatory with 72.33 &71.17% inhibition along analgesic activity having 67.89% and 71.37 % respectively. Their selectivity against COX-II enzyme with selectivity index 67.81 and 66.38 was established for 6b and 6m, which is compared with Celecoxib. During the gastric ulceration study, selected compounds couldn't observed any ulcerogenic effect on gastric mucosa. The in-silico pharmacokinetic profile and molecular docking study exposed very good binding affinity towards the Cyclooxygenase (COX-II) enzyme (PDB Id: 3PGH), therefore the compounds 6b and 6m are used as promising lead candidates for the support of drug development.
- Alam, Md. Jahangir,Alam, Ozair,Ali, Md. Rahmat,Naim, Mohd. Javed,Khan, Suroor Ahmad
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p. 1873 - 1885
(2016/02/27)
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- Novel 4-thiazolidinones as non-nucleoside inhibitors of hepatitis C virus NS5B RNA-dependent RNA polymerase
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In continuation of our efforts to develop new derivatives as hepatitis C virus (HCV) NS5B inhibitors, we synthesized novel 5-arylidene-4-thiazolidinones. The novel compounds 29-42, together with their synthetic precursors 22-28, were tested for HCV NS5B inhibitory activity; 12 of these compounds displayed IC50 values between 25.3 and 54.1 μM. Compound 33, an arylidene derivative, was found to be the most active compound in this series with an IC50 value of 25.3 μM. Molecular docking studies were performed on the thumb pocket-II of NS5B to postulate the binding mode for these compounds.
- akir, Gizem,Kücükgüzel, Ilkay,Guhamazumder, Rupa,Tatar, Esra,Manvar, Dinesh,Basu, Amartya,Patel, Bhargav A.,Zia, Javairia,Talele, Tanaji T.,Kaushik-Basu, Neerja
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-
- Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif
-
A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA.
- Guan, Peng,Wang, Lei,Hou, Xuben,Wan, Yichao,Xu, Wenfang,Tang, Weiping,Fang, Hao
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p. 5766 - 5775
(2015/02/02)
-
- Synthesis of N-(5-aryl-1,3,4-thiadiazol-2-yl)-2-(3-oxo-1,2-benzothiazol- 2(3H)-yl)acetamide derivatives promoted by carbodiimide condensation
-
Novel N-(5-aryl-1,3,4-thiadiazol-2-yl)-2-(3-oxo-1,2-benzothiazol-2(3H)-yl) acetamide derivatives were prepared by 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride and N-hydroxybenzotrizole condensation catalysis in a convenient and fast method
- Yu, Peng,Hu, Jun,Wan, Rong,Li, Xi,Zheng, Shanlong,Xu, Yanhua
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p. 347 - 350
(2014/07/08)
-
- One-pot synthesis of 5H-1,3,4-thiadiazolo[3,2-a] pyrimidin-5-one derivatives
-
A novel and efficient one-pot method has been developed for the synthesis of 2-substituted-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5- one derivative by the combination of [3 + 3] cycloaddition, reduction, deamination reactions. The fused heterocyclic compoun
- Dong, Hong-Ru,Gao, Zhong-Lian,Li, Rong-Shan,Hu, Yi-Ming,Dong, Heng-Shan,Xie, Zhi-Xiang
-
p. 55827 - 55831
(2015/01/16)
-
- Synthesis and pharmacological activity of certain thiadiazolo [2',3':2,3] imidazo [4,5-B] quinoxalines
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Derivatives of thiadiazolo [2',3':2,3] imidazo [4,5-b] quinoxalines were synthesized by the reaction of 5-substituted-1,3,4-thiadiazol-2-amine with 2,3-dichloro-6,7- dinitroquinoxalines. The synthesized compounds were characterized by using spectral data. They were then screened for analgesic, anti-inflammatory and ulcerogenic activity.
- Visagaperumal,Jayakumar,Anbalagan
-
p. 311 - 314
(2019/01/21)
-
- Synthesis, bioevaluation and docking study of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents
-
Since the first histone deacetylase (HDAC) inhibitor (Zolinza, widely known as suberoylanilide hydroxamic acid; SAHA) was approved by the Food and Drug Administration for the treatment of T-cell lymphoma in 2006, the search for newer HDAC inhibitors has attracted a great deal of interest of medicinal chemists worldwide. As a continuity of our ongoing research in this area, we designed and synthesized a series of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as analogues of SAHA and evaluated their biological activities. A number of compounds in this series, for example, N1-hydroxy-N8-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5b), N1-hydroxy-N8-(5-(3-chlorophenyl-1,3,4-thiadiazol-2-yl)octandiamide (5c) and N1-hydroxy-N8-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5d), were found to possess potent anticancer cytotoxicity and HDAC inhibition effects. Compounds 5b-d were generally two- to five-fold more potent in terms of cytotoxicity compared to SAHA against five cancer cell lines tested. Docking studies revealed that these hydroxamic acid displayed higher affinities than SAHA toward HDAC8.
- Nam, Nguyen-Hai,Huong, Tran Lan,Dung, Do Thi Mai,Dung, Phan Thi Phuong,Oanh, Dao Thi Kim,Park, Sang Ho,Kim, Kyungrok,Han, Byung Woo,Yun, Jieun,Kang, Jong Soon,Kim, Youngsoo,Han, Sang-Bae
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p. 611 - 618
(2015/02/18)
-
- Discovery and biophysical characterization of 2-amino-oxadiazoles as novel antagonists of PqsR, an important regulator of Pseudomonas aeruginosa virulence
-
The human pathogen Pseudomonas aeruginosa employs alkyl quinolones for cell-to-cell communication. The Pseudomonas quinolone signal (PQS) regulates various virulence factors via interaction with the transcriptional regulator PqsR. Therefore, we consider t
- Zender, Michael,Klein, Tobias,Henn, Claudia,Kirsch, Benjamin,Maurer, Christine K.,Kail, Dagmar,Ritter, Christiane,Dolezal, Olan,Steinbach, Anke,Hartmann, Rolf W.
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p. 6761 - 6774
(2013/10/01)
-
- Mild and convenient one-pot synthesis of 2-amino-1,3,4-thiadiazoles using trimethylsilyl isothiocyanate (TMSNCS)
-
A novel and efficient one-pot method has been developed for the synthesis of 2-amino-1,3,4-thiadiazoles using various carboxylic acid hydrazides with trimethylsilyl isothiocyanate (TMSNCS). In situ preparation of various thiosemicarbazides by the reaction
- Guda, Dinneswara Reddy,Cho, Hyeon Mo,Lee, Myong Euy
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p. 6813 - 6816
(2013/05/22)
-
- New thiazolidinedione-5-acetic acid amide derivatives: Synthesis, characterization and investigation of antimicrobial and cytotoxic properties
-
The present work describes the synthesis, antimicrobial and cytotoxic activity of 2,4-thiazolidinedione- 5-acetic acid amides 3a-n. The structures of the compounds were confirmed by IR, 1H, 13C NMR and elemental analysis. All compounds were tested for antimicrobial activity by twofold serial dilution technique. The preliminary results revealed that the compound 3d exhibits promising antibacterial and antifungal activity. The cytotoxic (MTT) activity of 2,4-thiazolidinedione-5-acetic acid amides were tested in four tumour cell lines. We found that compound 3j inhibited proliferation of HeLa, HT29, A549 and MCF-7 cell lines with IC50 values of 33, 35, 30 and 36 μM, respectively. Springer Science+Business Media, LLC 2011.
- Alegaon, Shankar G.,Alagawadi, Kallanagouda R.
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experimental part
p. 816 - 824
(2012/10/07)
-
- Synthesis, insecticidal evaluation of novel 1,3,4-thiadiazole chrysanthemamide derivatives formed by an EDCI/HOBt condensation
-
A series of novel pesticides with two components derived from a 1,3,4-thiadiazole and chrysanthemic acid were synthesised via an EDCI/HOBt condensation. These 1,3,4-thiadiazole chrysanthemamides were identified by IR, 1H NMR and elemental analyses. Their insecticidal activity was also evaluated.
- Yu, Peng,Hu, Jun,Zhou, Tao-Yu,Wang, Peng,Xu, Yan-Hua
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experimental part
p. 703 - 706
(2012/03/10)
-
- Thiadiazole derivatives as potential anticonvulsant agents
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A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR,1HNMR,13C NMR and mass spectral data confir
- Mullick, Pooja,Khan, Suroor A.,Verma, Surajpal,Alam, Ozair
-
experimental part
p. 1011 - 1016
(2012/01/03)
-
- Synthesis of some new triazole incorporated imidazo [2,1-b]-1,3,4- thiadiazoles
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A series of 6-[5-methyl-1 -(p-tolyl)-lH-1,2,3-triazol-4-yl]-2-substituted imidazo [2,1-b]-1,3,4-thiadiazoles 7 were synthesized by the reaction of 2-amino-5-substituted-1,3,4-thiadiazoles 6 with 2-bromo-1-[5-methyl-1-(p-tolyl)- 1H-1,2,3-triazol-4-yl] ethanone 4. Their structures were confirmed by 1H NMR, MS and IR spectra.
- Wang, Yan-Fei,Shen, Guo-Liang,Li, Rong-Shan,Dong, Heng-Shan
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p. 403 - 404
(2013/09/24)
-
- Efficient synthesis of antifungal active 9-substituted-3-aryl-5H,13aH- quinolino[3,2-f][1,2,4]triazolo[4,3-b][1,2,4]triazepines in ionic liquids
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The title compounds, 9-substituted-3-aryl-5H,13aH-quinolino[3,2-f][1,2,4] triazolo[4,3-b][1,2,4]triazepines 8, are synthesized from 5-aryl-3,4-diamino-1, 2,4-triazoles 5 and 2-chloro-3-formylquinolines 7 in ionic liquid as solvent under microwave heating as well as using oil-bath heating at 80 °C. The products are obtained in the good to moderate yields and in high purity. These compounds have been screened for antifungal activity. The screening data indicate that the compounds 8a, 8b, 8c and 8d show excellent activity against Aspergillus niger 1000 μg concentration and Pencillium notatum species at 500 μg as well as 1000 μg concentrations whereas, these compounds show good to moderate activity against Aspergillus flavus and Rhizopus species at both the concentrations. Moreover, ionic liquid is found to be recyclable for at least three consecutive runs what makes the process cost-effective and economic that lead to the area of Green Chemistry as recyclability is one of the most important feature of Green Chemistry.
- Gupta, Monika
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scheme or table
p. 4919 - 4923
(2011/09/16)
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- 2,5-Disubstituted-1,3,4-oxadiazoles/thiadiazole as surface recognition moiety: Design and synthesis of novel hydroxamic acid based histone deacetylase inhibitors
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The enzymatic inhibition of histone deacetylase activity has come out as a novel and effectual means for the treatment of cancer. Two novel series of 2-[5-(4-substitutedphenyl)-[1,3,4]-oxadiazol/thiadiazol-2-ylamino] -pyrimidine-5-carboxylic acid (tetrahydro-pyran-2-yloxy)-amides were designed and synthesized as novel hydroxamic acid based histone deacetylase inhibitors. The antiproliferative activities of the compounds were investigated in vitro using histone deacetylase inhibitory assay and MTT assay. The synthesized compounds were also tested for antitumor activity against Ehrlich ascites carcinoma cells in Swiss albino mice. The efforts were also made to establish structure-activity relationships among synthesized compounds. The results of the present studying indicates 2,5-disubstituted 1,3,4-oxadiazole/thiadiazole as promising surface recognition moiety for development of newer hydroxamic acid based histone deacetylase inhibitor.
- Rajak, Harish,Agarawal, Avantika,Parmar, Poonam,Thakur, Bhupendra Singh,Veerasamy, Ravichandran,Sharma, Prabodh Chander,Kharya, Murli Dhar
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supporting information; scheme or table
p. 5735 - 5738
(2011/10/09)
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- Synthesis, characterization and antimicrobial activity of new thiadiazole derivatives
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A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, 1H NMR, 13C NMR and mass spectral data confirmed the
- Mullick, Pooja,Khan, Suroor A.,Verma, Surajpal,Alam, Ozair
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experimental part
p. 2345 - 2350
(2010/11/16)
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- One-pot synthesis of antifungal active 9-substituted-3-aryl-5H,13aH- quinolino [3,2-/][1,2,4]triazolo [4,3-b] [1,2,4]triazepines
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The title compounds, 9-substituted-3-aryl-5H,13aH-quinolino[3,2-f][1,2,4] triazolo[4,3-b][1,2,4]triazepines 8, are synthesized from 5-aryl-3,4-diamino-1, 2,4-triazoles 5 and 2-chloro-3-formylquinolines 7 using catalytic amount of p-TsOH and N,N-dimethylformamide as an energy transfer medium using microwave heating as well as solvent using oil-bath heating at 80°C affords novel 9-substituted-3-aryl-5H,13aH-quinolino[3,2-f][1,2,4]triazolo[4,3-b][1,2,4] triazepines. The products are obtained in good to moderate yields and are in a state of high purity.
- Gupta, Monika,Paul, Satya,Gupta, Rajive
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scheme or table
p. 475 - 481
(2010/10/03)
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- Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamides
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A series of cyclopropanecarboxamide were prepared and tested for antifungal activity in vivo. The preliminary bioassays indicated that some compounds are comparable to the commercial fungicides. To further explore the comprehensive structure-activity relationship on the basis of fungicidal activity data, comparative molecular field analysis (CoMFA) was performed, and a statistically reliable model with good predictive power (r2 = 0.8, q2 = 0.516) was achieved. Based on the CoMFA, compound 7p was designed and synthesized, which was found to display a good antifungal activity (79.38%) as 7g and 7h.
- Liu, Xing-Hai,Shi, Yan-Xia,Ma, Yi,Zhang, Chuan-Yu,Dong, Wei-Li,Pan, Li,Wang, Bao-Lei,Li, Bao-Ju,Li, Zheng-Ming
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scheme or table
p. 2782 - 2786
(2009/10/19)
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- Phase transfer catalysts promoting the one-pot synthesis under ultrasonic irradiation and biological activity of n-(5-substituted-1,3,4-thiadiazole-2-yl)- N'-(5-methylisoxazoyl)-thiourea derivatives
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Reaction of 2-amino-5-substitute-1,3,4-thiadiazoles with 5-methylisoxazoyl chloride and ammonium thiocyanate under the condition of solid-liquid phase-transfer catalysis using polyethylene glycol-600 (PEG-600) as the catalyst under ultrasonic irradiation yielded N-(5-substituted-1,3,4-thiadiazole-2-yl)- N'-(5-methylisoxazoyl)-thiourea derivatives 3a-1 in good-to-excellent yield. The chemical structure of all compounds was established by 1H NMR, FTIR, MS, and elemental analysis studies. Some of the compounds were investigated for fungicidal activity. The bioassay results indicated that some of these compounds exhibit moderate fungicidal activities.
- Xiaodong, Yang
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p. 387 - 392
(2008/09/19)
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- Synthesis and antifungal activity of novel 3,6-diaryl-5H-[1,2,4]triazolo[4, 3-b][1,2,4]triazepines
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(Chemical Equation Presented) 5-Aryl-3,4-diamino-1,2,4-triazoles 5 on treatment with β-chlorocinnamaldehydes 7 in the presence of catalytic amount of p-TsOH and N,N-dimethylformamide as an energy transfer medium under microwave irradiation and as solvent with oil-bath heating at 80°C affords novel 3,6-diaryl-5H-[1,2,4]triazolo[4,3-b]-1,2,4]triazepines 8. The structures of the synthesized compounds were established on the basis of 1H NMR, IR, mass spectral data and elemental analysis.
- Gupta, Monika
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p. 1023 - 1027
(2008/03/29)
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- Synthesis of thiadiazolo-s-triazines for their antiviral activity based on QSAR studies
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2-Amino-5-aralkyl-1,3,4-thiadiazole 1 on treatment with benzaldehyde yields 5-aralkyl-2-benzylideno-imino-1,3,4-thiadiazole 2 which on reaction with ammonium thiocyanate cyclises to give 2-phenyl-7-aralkyl-1,3,4-thiadiazolo-[3,2-a]-s-triazine-5-[6H,7H]-thione 3. Reaction of 3 with p-toluene sulphonyl chloride in anhydrous chloroform gives 2-phenyl-3-(p-toluenesulphonyl)-7-aralkyl-1,3,4-thiadiazolo-[3, 2-al-s-triazine-5-[6H,7H]-thiones 4g-I. Benzoyl chloride also reacts with 3 in anhydrous pyridine giving 2-phenyl-3-(benzoyl)-7-aralkyl-1,3,4-thiadiazolo-[3,2-a]-s-triazine-5-[6H,7H] -thiones 4a-f in quantitative yields. The antiviral activities of 4 based on QSAR studies have been reported using physicochemical method.
- Pandey,Tusi,Tandon,Joshi,Bajpai
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p. 2583 - 2588
(2007/10/03)
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- Studies on biologically active heterocycles: Part X - Synthesis of 2-amino-4-[5-(2-chlorophenyl)-1,3,4-oxa/thiadiazol}-2-yl]6-aryl/substituted aryl-7-oxo-6,7-dihydrothiazolo[4,5-d]pyrimidine-5(H)-thiones as probable bioactive compounds
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A series of new 2-amino-4-[5-{(2-chlorophenyl)-1,3,4-oxadiazolo}-2-yl]-6-aryl/ substituted-aryl-7-oxo-6,7-dihydrothia zolo[4,5-d]pyrimidine-5(H)-thiones 8a-h and 2-amino-4-[5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl]-6-aryl/ substituted-aryl-7-oxo-6,7-dihydrothiazolo[4,5-d]pyrimidine-5(H)-thiones 9a-h have been synthesized from 3-[5-(2-chlorophenyl)-1,3,4-oxa/thiadiazol-2-yl]-l-aryl/ substituted-arylthiobarbituric acid 6, 7 which in turn are prepared from N-aryl/substituted-aryl, N-5-[(2-chlorophenyl)-1,3,4-oxa/thiadiazol-2-yl]thioureas 4, 5 on treatment with malonic acid, acetyl chloride and thiourea respectively in the presence of chlorine. All the newly synthesized compounds have been characterized by their elemental analysis, physical and spectroscopic data. These substituted oxa/thiadiazolthiones are screened for their fungitoxic and antibacterial properties.
- Hazarika,Kataky
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p. 255 - 257
(2007/10/03)
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- Studies on the synthesis and bioactivity of some thiadiazole derivatives
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Several 2-aryl-3-(4-aryl-1,3,4-thiadiazolyl)-4-thiazolidinones 3 and several other fused heterocycles 5 have been prepared. Most of the compounds 3 have been screened for their fungicidal activity against two fungi Aspergillus clavatus and Aspergillus fum
- Padhy, Arun Kumar,Nag,Panda
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p. 998 - 1001
(2007/10/03)
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- Antihypertensive Thiadiazoles. 1. Synthesis of Some 2-Aryl-5-hydrazino-1,3,4-thiadiazoles with Vasodilator Activity
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Some 2-Aryl-5-hydrazino-1,3,4-thiadiazoles have been synthesized and screened for antihypertensive activity.In general, compounds with a 2-substituted phenyl ring had higher activity than their 3- or 4-substituted counterparts or those containing heteroar
- Turner, Stephen,Myers, Malcolm,Gadie, Brian,Nelson, Anthony J.,Pape, Robin,et al.
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p. 902 - 906
(2007/10/02)
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- 1,4-Cycloaddition of Isothiocyanates to Azomethines and Fungitoxicity of Resulting 1,3,4-Thiadiazolo-s-triazine-5(6H,7H)-thiones
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Several 2,6,7-trisubstituted 1,3,4-thiadiazolo-s-triazine-5(6H,7H)-thiones have been prepared by 1,4-cycloaddition of aryl isothiocynates to 5-aryl(aryloxymethyl-2-benzylidene-amino-1,3,4-thiadiazoles (3a-e).The fungicidal activity of compounds has
- Singh, H.,Yadav, L. D. S.,Sharma, K. S.
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p. 480 - 481
(2007/10/02)
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- Synthesis and Antifungal Activity of Some 1,3,4-Thiadiazolo-s-triazine-7-thiones and N-Acyl-N'-(5-aralkyl/aryl-1,3,4-thiadiazol-2-yl)thioureas
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1-Acylthiosemicarbazides (1) on cyclodehydration with conc.H2SO4 give the corresponding 2-amino-5-aralkyl/aryl-1,3,4-thiadiazoles (2) which on treatment with acyl chlorides and NH4SCN in acetone followed by cyclisation of the resultant N-acyl-N'-(5-aralky
- Singh, S.,Yadav, L. D. S.,Singh, H.
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p. 518 - 520
(2007/10/02)
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