Investigation of triazole-linked indole and oxindole glycoconjugates as potential anticancer agents: novel Akt/PKB signaling pathway inhibitors

Abstract

Novel triazole-linked indole and oxindole glycoconjugates as inhibitors of the Akt/PKB signaling pathway.

Synthesis of (E)‐3‐Alkylideneindolin‐2‐ones by an Iron‐Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines

“…[1b,1f,16] Compound 6 could be prepared by a three-step procedure involving the oxidative condensation of oxindole (1a) with 4-bromobenzylamine (2j) to give (E)-3-(4bromobenzylidene)indolin-2-one (4j) in 93 % yield under the optimized reaction conditions, followed by Buchwald-Hartwig amination, and N-formylation reaction as shown in Scheme 4a. In addition, (E)-3-(benzo[d] [1,3]dioxol-5-ylmethylene)indolin-2one (4h) and (E)-3-(3,4,5-trimethoxybenzylidene)-5-methoxyindolin-2-one (9) are identified as potent anticonvulsant agent and antitumor agent, respectively. [1c,17] Compound 9 could be synthesized by oxidative reaction of 5-methoxyoxindole 7with 3,4,5-trimethoxybenzylamine (8) under the standard conditions (Scheme 4b).…”

“…[10] m.p. 203-204°C); 1 6, 160.9, 141.3, 137.8, 131.5, 129.4, 127.1, 125.6, 122.7, 121.9, 121.7, 114.1, 110.1, 55.4 3,141.8,140.8,139.3,136.3,133.3,132.8,130.3,129.2,128.1,126.9,126.8,126.4,125.1,121.2,119.9,109.5;HRMS (ESI) 3-(3,4,5-Trimethoxybenzylidene)indolin-2-one (4g). Yellow solid; yield: 85 %; m.p.…”

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

“…Nagarsenkar et al . have reported the synthesis of two different sets of triazole linked indole and oxindole glycoconjugates by this procedure that 1,2,3,4,6‐penta‐O‐acetyl‐Dglucopyranose was reacted with HBr in acetic acid at room temperature and then NaN 3 in DMF as a solvent was added to the reaction mixture at room temperature.…”

Novel sulfonamide benzoquinazolinones as dual EGFR/HER2 inhibitors, apoptosis inducers and radiosensitizers

“…Molecular hybridization is a simple and effective tool to combine covalently two drug pharmacophores into a single molecule 13 . Lately, it has been observed that benzo[g]quinazoline and sulphonamides demonstrated profound growth inhibitory activity against different cancer cells and TK enzymes 14 , 15 .…”