Synthesis of some novel heterocyclic compounds derived from diflunisal hydrazide as potential anti-infective and anti-inflammatory agents

Anti-cancer and anti-hepatitis C virus NS5B polymerase activity of etodolac 1,2,4-triazoles

“…Moreover, in the 1 H-NMR spectra of etodolac triazoles, additional signals due to the NH group were appeared in the region of 13.38-13.82 ppm, whereas S-H proton at 1.0-3.7 ppm was not detected which also confirmed the formation of their thionic form 25 . Triazole NH resonances were observed to be shifted to downfield because of strong intermolecular hydrogen bonding as previously reported 26,27 .…”

1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans

“…In spite of the development of new drugs, such as new azole or echinocandin derivatives, there has been a dramatic increase in both anti-Candida resistance and the frequency of invasive Candida infections (Pfaller, 2012). Among enormous classes of heterocyclic compounds, the synthesis of new derivatives of 1,2,4-triazole-3-thiones and 2-amino-1,3,4-thiadiazoles has been attracting considerable attention because of their broad biological activity, including antibacterial and antifungal (Güzeldemirci, Küçükbasmaci, 2010;Plec et al, 2011;Camoutsis et al, 2010;Küçükgüzel et al, 2007;Kadi et al, 2007), anti-tubercular (Küçükgüzel et al, 2001;Küçükgüzel et al, 2008), antiviral (Abdel-Aal et al, 2003;Küçükgüzel et al, 2008), antioxidant (Ayhan-Kilcigil et al, 2004;Khan et al, 2010), antitumoral Rzeski, Matysiak, Kandefer-Szerszen, 2007;Mavrova et al, 2009), anti-inflammatory (Amir, Shikha, 2004;Kadi et al, 2007;Küçükgüzel et al, 2007;Kumar et al, 2008), and anticonvulsant activity (Kane et al, 1994;Sharma et al, 2011;Dogan et al, 2002). Clinically-used antifungal azole drugs containing either an imidazole (e.g., econazole, miconazole, clotrimazole, and ketoconazole) or a 1,2,4-triazole moiety (e.g., fluconazole and itraconazole) have a high therapeutic index and significant safety profile (Wang et al, 2009).…”

Iodocyclization of S-allyl derivatives of 3-mercapto-4-methyl-1,2,4-triazole

“…Derivatives of 3-mercapto-1,2,4-triazoles (1,2,4-triazol-3-thiones) possess a broad spectrum of physiological activity: analgetic, vasodilator, antitumor, bactericidal, and hypotensive effects [1][2][3][4].…”

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Keywords: 3-allylthio-4-methyl-1,2,4-triazole, [1,3]thiazolo [3,2-b][1,2,4]triazolium iodide, [1,2,4]triazolo[5,1-b][1,3]thiazinium iodide, 3-(3-methyl-2-butenyl)thio-4-methyl-1,2,4-triazole, 3-mercapto-4-methyl-1,2,4-triazole, 3-(2-methyl-2-propenyl)thio-4-methyl-1,2,4-triazole, iodocyclization.Derivatives of 3-mercapto-1,2,4-triazoles (1,2,4-triazol-3-thiones) possess a broad spectrum of physiological activity: analgetic, vasodilator, antitumor, bactericidal, and hypotensive effects [1][2][3][4].The reaction of 5-phenyl-, methyl-, and tert-butyl-3-allylthio-1,2,4-triazoles with iodine gave a mixture of products of iodocyclization at the N(2) and N(4) atoms [5,6]. In this work we have synthesized 3-allylthio-(2a), 3-(2-methyl-2-propenyl)thio-(2b), and 3-(3-methyl-2-butenyl)thio-1,2,4-triazole (2c) respectively by the reaction of 3-mercapto-4-methyl-1,2,4-triazole (1) in 2-propanol in the presence of alkali or sodium isopropoxide with 3-bromopropene, 3-chloro-2-methylpropene, and 1-bromo-3-methyl-2-butene, and we have studied their reaction with iodine.

It has been established that compound 2a reacted with excess iodine in ether to form a mixture of two products of iodocyclization -6-iodomethyl-3-methyl-5,6-dihydro[1,3]thiazolo[3,2-b][1,2,4]triazolium (3a) and 6-iodo-3-methyl-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]thiazinium (4a) polyiodides (a mixture of triiodides and pentaiodides) in a ratio of 0.17:1.00 (according to 1 H NMR spectral data).

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