- Synthesis of 5-alkyl-2-amino-1,3,4-thiadiazoles and α,ω-bis(2- amino-1,3,4-thiadiazol-5-yl)alkanes in ionic liquids
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Reaction of thiosemicarbazide with carboxylic acids, including N-substituted amino acids, in ionic liquids with H2SO4 as a catalyst affords 5-R-2-amino-1,3,4-thiadiazoles. On using alkanedicarboxylic acids, α,ω-bis(2-amino-1,3,4,-thiadiazol-5-yl)alkanes were obtained.
- Epishina, Margarita A.,Kulikov, Alexander S.,Ignat'Ev, Nikolai V.,Schulte, Michael,Makhova, Nina N.
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- Synthesis of novel five-membered nitrogen-containing heterocyclic compounds from derivatives of arylsulfonyl- and arylthioacetic and -propionic acids
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A series of novel substituted 1,3,4-oxa(thia)diazoles and triazoline-3-thiones has been synthesized from thiosemicarbazides and nitriles of arylthio-, arylsulfonylacetic and -propionic acids. A mechanism is proposed for the preparation of 2-amino-5-substi
- Golovlyova,Moskvichev,Alov,Kobylinsky,Ermolaeva
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Read Online
- 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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- 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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- Gamma-glutamyl transpeptidase inhibitors and methods of use
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Compositions that are effective in inhibiting gamma-glutamyl transpeptidase are disclosed. Methods of producing and using these compositions are also disclosed.
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Page/Page column 4; 27
(2017/01/31)
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- Synthesis and antiinflammatory activity of some imidazo[2,1-b][1,3,4]thiadiazole derivatives
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A number of imidazo[2,1-b][1,3,4]thiadiazole derivatives having alkyl and aryl moieties attached to positions 2 and 6 of imidazo[2,1-b][1,3,4]thiadiazole nucleus, respectively, were prepared and characterized by IR, NMR and mass spectroscopy. Antiinflamma
- Karki, Subhas S.,Rana, Vivek,Sivan, Ramjith U.,Kumar, Sujeet,Renuka, Vinayakumar,Ramareddy, Sureshbabu A.,Subbarao, Prasanna G.,Si, Sudam C.
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p. 931 - 936
(2015/10/12)
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- Synthesis and antiproliferative assay of norcantharidin derivatives in cancer cells
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Diels-Alder reaction between furan and maleic anhydride resulted in 5,6-dehydro norcantharidin, then norcantharidin was obtained by reduction. The substituted-carboxylic acid was condensed with N-aminothiourea in presence of phosphorus oxychloride, yielding 2-amino-1,3,4-thiadiazole derivatives. Novel norcantharidin derivatives were synthesized with acylation, then intramolecular condensation using norcantharidin (or 5,6-dehydro norcantharidin) and 2-amino-1,3,4-thiadiazole derivatives. All the target compounds were confirmed by IR, 1HNMR, ESI-MS and were reported for the first time. Norcantharidin derivatives antiproliferative assay was tested by MTT method against A549 and PC-3 cell lines. The results showed that all the norcantharidin derivatives displayed moderate inhibitory activities.
- Tu, Guo Gang,Zhan, Jian Feng,Lv, Qiao Li,Wang, Jia Qi,Kuang, Bin Hai,Li, Shao Hua
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p. 376 - 381
(2014/05/20)
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- One-pot synthesis of 5H-1,3,4-thiadiazolo[3,2-a] pyrimidin-5-one derivatives
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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
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p. 55827 - 55831
(2015/01/16)
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- Design, synthesis and preliminary bioactivity studies of 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors
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Histone deacetylase (HDAC) inhibitors have emerged as a new class of anticancer agents, targeting the biological processes including cell cycle, apoptosis and differentiation. In the present study, a series of 1,3,4-thiadiazole based hydroxamic acids were developed as potent HDAC inhibitors. Some of them showed good inhibitory activity in HDAC enzyme assay and potent growth inhibition in some tumor cell lines. Among them, compound 6i (IC50 = 0.089 μM), exhibited better inhibitory effect compared with SAHA (IC50 = 0.15 μM).
- Guan, Peng,Sun, Feng'E,Hou, Xuben,Wang, Feng,Yi, Fan,Xu, Wenfang,Fang, Hao
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experimental part
p. 3865 - 3872
(2012/08/27)
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- Microwave-assisted synthesis and antimicrobial activity of some imidazo[2,1-b][1,3,4]thiadiazole derivatives
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A simple and efficient method was developed for the synthesis of 2,6-disubstituted-imidazo[2,1-b][1,3,4] thiadiazoles under microwave (MW) activation using 2-amino-5-substituted-1,3,4-thiadiazoles and appropriate bromo ketones as materials. All reactions
- Dhepe, Sharad,Kumar, Sujeet,Vinayakumar,Ramareddy, Sureshbabu A.,Karki, Subhas S.
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p. 1550 - 1556
(2012/11/07)
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- Divergent effects of compounds on the hydrolysis and transpeptidation reactions of γ-glutamyl transpeptidase
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A novel class of inhibitors of the enzyme γ-glutamyl transpeptidase (GGT) were evaluated. The analog OU749 was shown previously to be an uncompetitive inhibitor of the GGT transpeptidation reaction. The data in this study show that it is an equally potent uncompetitive inhibitor of the hydrolysis reaction, the primary reaction catalyzed by GGT in vivo. A series of structural analogs of OU749 were evaluated. For many of the analogs, the potency of the inhibition differed between the hydrolysis and transpeptidation reactions, providing insight into the malleability of the active site of the enzyme. Analogs with electron withdrawing groups on the benzosulfonamide ring, accelerated the hydrolysis reaction, but inhibited the transpeptidation reaction by competing with a dipeptide acceptor. Several of the OU749 analogs inhibited the transpeptidation reaction by slow onset kinetics, similar to acivicin. Further development of inhibitors of the GGT hydrolysis reaction is necessary to provide new therapeutic compounds.
- Wickham, Stephanie,Regan, Nicholas,West, Matthew B.,Kumar, Vidya Prasanna,Thai, Justin,Li, Pui Kai,Cook, Paul F.,Hanigan, Marie H.
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experimental part
p. 476 - 489
(2012/09/22)
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- 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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p. 4919 - 4923
(2011/09/16)
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- 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)
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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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- THIADIAZOLE DERIVATIVES, INHIBITORS OF STEAROYL-COA DESATURASE
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The present invention relates to substituted thiadiazole compounds of the formula (I) and pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for modulating SCD activity.
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Page/Page column 57
(2008/12/07)
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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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- Novel selective inhibitors of neutral endopeptidase for the treatment of female sexual arousal disorder. Synthesis and activity of functionalized glutaramides
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Female sexual arousal disorder (FSAD) is a highly prevalent sexual disorder affecting up to 40% of women. We describe herein our efforts to identify a selective neutral endopeptidase (NEP) inhibitor as a potential treatment for FSAD. The rationale for this approach, together with a description of the medicinal chemistry strategy, lead compounds, and SAR investigations are detailed. In particular, the strategy of starting with the clinically precedented selective NEP inhibitor, Candoxatrilat, and targeting low molecular weight and relatively polar mono-carboxylic acids is described. This led ultimately to the prototype development candidate R-13, for which detailed pharmacology and pharmacokinetic parameters are presented.
- Pryde, David C.,Maw, Graham N.,Planken, Simon,Platts, Michelle Y.,Sanderson, Vivienne,Corless, Martin,Stobie, Alan,Barber, Christopher G.,Russell, Rachel,Foster, Laura,Barker, Laura,Wayman, Christopher,Van Der Graaf, Piet,Stacey, Peter,Morren, Debbie,Kohl, Christopher,Beaumont, Kevin,Coggon, Sara,Tute, Michael
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p. 4409 - 4424
(2007/10/03)
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- Derives de la dihydro-2,4 triazole-1,2,4 thione-3 et de l'amino-2 thiadiazole-1,3,4 a partir de nouvelles thiosemicarbazones d'esters
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A new general synthesis of 4,5-disubstituted 2,4-dihydro-1,2,3-triazole-3-thiones is proposed.These heterocycles are obtained by the action of primary amines, aralhydrazines or aroylhydrazines on the thiosemicarbazones of esters.These last compounds are prepared by action of chlorhydrates of iminoesters on thiosemicarbazide in dimethylformamide.These thiosemicarbazones react also with strong acids, acid anhydrides and chlorides; by thermolysis and they give 2-amino-1,3,4-thiadiazole derivatives.Also, two derivatives of 1,2,4-triazolo-1,3,4-thiadiazole have been prepared.
- Malbec, Frederique,Milcent, Rene,Barbier, Geo
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p. 1689 - 1698
(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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- A Convenient and General Synthesis of 2-Amino-1,3,4-thiadiazoles. Dehydration of Acylthiosemicarbazides with Methanesulfonic Acid
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2-Amino-5-alkyl and 2-amino-5-aryl-1,3,4-thiadiazoles were prepared by the dehydration of 2-acylthiosemicarbazides with molar equivalents of methanesulfonic acid in refluxing toluene.The synthesis appears to be general.
- Kress, Thomas J.,Costantino, Silvio M.
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p. 607 - 608
(2007/10/02)
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