- Synthesis of New Substituted 1,2,4-Triazoles and 1,3,4-Thiadiazoles and Their Effects on DNA Methylation Level
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Continuing the search for biologically active compounds among functionally substituted azoles, new 1,2,4-triazole-3-thiols and 1,3,4-thiadiazoles derivatives bearing pharmacologically active carboxamide, hydroxyl or carboxyalkyl moieties, as well as N-acy
- Hovsepyan,Hakobyan,Muradyan,Nersesyan,Agaronyan,Danielyan,Minasyan
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p. 673 - 679
(2019/06/27)
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- Alkylation of 1,2,4-triazole-3-thiols with haloalkanoic acid esters
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Alkylation of 4,5-disubstituted 4H-1,2,4-triazole-3-thiols with methyl chloroformate and ethyl chloroacetate chemoselectively afforded the corresponding S-alkyl derivatives, whereas the alkylation of 5-benzyl-4-phenyl-4H-1,2,4-triazole-3-thiol with methyl 3-bromopropanoate gave an inseparable mixture of S- and N-alkylation products. Hydrazinolysis of S-(5-benzyl-4-phenyl-4H-1,2,4-triazol-3-yl) methyl carbonothioate involved anomalous cleavage with formation of the initial 4,5-disubstituted 1,2,4-triazole and methyl hydrazinecarboxylate.
- Samvelyan,Ghochikyan,Grigoryan,Tamazyan,Aivazyan
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p. 935 - 940
(2017/08/02)
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- Alkylsulfanyl-1,2,4-triazoles, a New Class of allosteric valosine containing protein inhibitors. Synthesis and structure-activity relationships
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Valosine containing protein (VCP), also known as p97, is a member of AAA ATPase family that is involved in several biological processes and plays a central role in the ubiquitin-mediated degradation of misfolded proteins. VCP is an ubiquitously expressed, highly abundant protein and has been found overexpressed in many tumor types, sometimes associated with poor prognosis. In this respect, VCP has recently received a great deal of attention as a potential new target for cancer therapy. In this paper, the discovery and structure-activity relationships of alkylsulfanyl-1,2,4-triazoles, a new class of potent, allosteric VCP inhibitors, are described. Medicinal chemistry manipulation of compound 1, identified via HTS, led to the discovery of potent and selective inhibitors with submicromolar activity in cells and clear mechanism of action at consistent doses. This represents a first step toward a new class of potential anticancer agents.
- Polucci, Paolo,Magnaghi, Paola,Angiolini, Mauro,Asa, Daniela,Avanzi, Nilla,Badari, Alessandra,Bertrand, Jay,Casale, Elena,Cauteruccio, Silvia,Cirla, Alessandra,Cozzi, Liviana,Galvani, Arturo,Jackson, Peter K.,Liu, Yichin,Magnuson, Steven,Malgesini, Beatrice,Nuvoloni, Stefano,Orrenius, Christian,Sirtori, Federico Riccardi,Riceputi, Laura,Rizzi, Simona,Trucchi, Beatrice,O'Brien, Tom,Isacchi, Antonella,Donati, Daniele,D'Alessio, Roberto
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p. 437 - 450
(2013/04/10)
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- Synthesis and antibacterial activity of some new derivatives of thiosemicarbazide and 1,2,4-triazole
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In a reaction of hydrazides of cyclohexylacetic acid 1 and phenylacetic acid 2 with isothiocyanates, respective thiosemicarbazide derivatives 3-18 were obtained. Further cyclization with 2% NaOH led to the formation of 5-(cyclohexylmethyl/benzyl)-4-substituted-2,4-dihydro-3H-1,2, 4-triazole-3-thiones 19-34. Structures of all new products were confirmed by analytical and spectroscopic methods. All compounds were screened for their in vitro activity against some species of bacteria and fungi. [Supplementary materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures and tables.]
- Wujec, Monika,Pachuta-Stec, Anna,Stefanska, Joanna,Kusmierz, Edyta,Siwek, Agata
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p. 1661 - 1669
(2013/10/21)
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- Experimental and theoretical study on 3-benzyl-4-phenyl-1,2,4-triazole-5- thione
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The 3-benzyl-4-phenyl-1,2,4-triazole-5-thione was synthesized and examined by elementary analysis, IR and electronic spectra. Density functional theory calculations of the structure, natural bond orbitais and thermodynamic functions of the title compound were performed at B3LYP/6-311G** level of theory. Vibrational frequencies were predicted, assigned and compared with the experimental data, and they are supported by the experimental data. Electronic absorption spectra were calculated by the time-dependent density functional theory (TD-DFT), which indicates that the two absorption bands are mainly derived from the contribution of bands π→π*. The calculation of the second order optical nonlinearity was carried out, giving value of molecular hyperpolarizabiliry equal to 4.025-10-30 esu. These calculated results were also compared with results obtained for a similar molecule, 4-phenyl-3-[(1,2,4-triazol-l-yl)methyl]-triazole-5-thione, reported earlier by this group.
- Zhao,Li,Xu,Zhang
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p. 1495 - 1503
(2008/09/18)
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- THIOTRIAZOLYL DERIVATIVES
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The invention relates to KvI.5 ion channel antagonists. Novel thiotriazolyl derivative compounds represented by Formula I, and synthesis and uses thereof for treating diseases mediated directly or indirectly by KvI.5 ion channels, are disclosed. Such cond
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Page/Page column 52
(2008/06/13)
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- 5-Sulphanyl-4h-1,2,4-triazole derivatives and their use as medicine
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The invention concerns novel 5-sulphanyl-4H-1,2,4-triazole derivatives of formula (1), wherein: R1, R2 and R3 represent variable groups and the methods for preparing them by liquid-phase parallel synthesis processes. Said product exhibit good affinity for certain sub-types of somatostatin receptors; they are particularly useful for treating pathological conditions or diseases wherein one (or more) somatostatin receptors is (are) involved. The invention also concerns pharmaceutical compositions containing said products and their use for preparing a medicine.
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Page/Page column 17
(2008/06/13)
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- Synthesis of some new 4,5-substituted-4H-1,2,4-triazole-3-thiol derivatives
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In this study appropriate hydrazide compounds, furan-2-carboxylic acid hydrazide (1) and phenylacetic acid hydrazide (2) were converted into 1,4-substituted thiosemicarbazides 4a-e and 5a-e and 4-amino-5-(furan-2-yl or benzyl)-4H-1,2,4-triazole-3-thiols 7
- Cansiz,Koparir,Demirdag
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p. 204 - 212
(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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