Synthesis and antitumor activity of new 1,2,4‐triazine and [1,2,4]triazolo[4,3‐b][1,2,4]triazine derivatives and their thioglycoside and acyclic C‐nucleoside analogs

Abstract

New 1,2,4‐triazine and their derived 1,2,4‐triazolo[3,4‐b][1,2,4]triazine derivatives were synthesized starting from 5,6‐diphenyl‐1,2,4‐triazine‐3‐thiol. Furthermore, the corresponding 1,2,4‐triazolo[3,4‐b][1,2,4]‐triazine thioglycosides and acyclic C‐nucleoside analogs were synthesized. The newly synthesized compounds were evaluated for their antitumor activity and some of them showed high inhibition activities. J. Heterocyclic Chem., 2011.

Synthesis and Antimicrobial Activity of New 2,5‐Disubstituted 1,3,4‐Oxadiazoles and 1,2,4‐Triazoles and Their Sugar Derivatives

“…However, it has been reported [42][43][44][45][46][47][48] that when the reaction was carried out at high temperature in boiling acetic anhydride, cyclization usually takes place in addition to per-O-acetylation to afford acyclic C-nucleoside analogs. We reported previously [38,42] the synthesis of 1,2,4-triazolo [1,3,4]oxadiazole and N-acetyl-1,3,4-oxadiazoline acyclic nucleoside analogs by the reaction of hydrazonyl sugars with boiling acetic anhydride. Thus, when the hydrazones 12 and 13 were heated in acetic anhydride at 100 ℃ they gave the 1,3,4-oxadiazoline acyclic nucleoside analogs 16 and 17, respectively.…”

“…[31][32][33][34][35] Oxadiazole and triazole ring systems have been reported to be synthesized either by cyclization of acyclic diacylhydrazines or ring conversion. [36] In view of the above facts and as continuation of interest in identification of new valuable candidates in designing new, potent and less toxic antimicrobial agents, [35,[37][38][39][40][41] we here report the synthesis and antimicrobial activity of new 2,5-disubstituted 1,3,4-oxadiazoles and 1,2,4triazoles as well as their derived acyclic C-nucleoside analogs incorporating both ring systems.…”

A Convenient Regioselective Synthesis of Novel 1,4‐Phenylenemethylene‐6,6′‐bis‐([1,2,4‐triazolo]‐[4,3‐b][1,2,4]‐triazin‐7(1H)‐ones)

“…While starting compound 4 revealed moderate cytotoxic activity against tested cell lines with IC 50 5.80, 7.90, and 8.80 μg/ml for HepG2, MCF 7, and HCT 116 cell lines. It was clear that the triazolotriazine group is more cytotoxic than triazine group .…”

Design, Synthesis, and Anticancer Activity of New Oxadiazolyl‐Linked and Thiazolyl‐Linked Benzimidazole Arylidines, Thioglycoside, and Acyclic Analogs

“…Figure displays examples of anticancer 1,3,4‐oxadiazole, thiazole, imidazole, and glycosyl hybrids . In view of these findings and our interest in the search for new heterocyclic glycosides with anticancer bioactivities, we report the synthesis and anticancer activity of new oxadizolyl‐based and imidazolyl‐based thiazolehybrids and their glycoside and acyclic nucleoside analogs.…”