Synthesis of Potent Anticancer Substituted 5-Benzimidazol-2-amino Thiazoles Controlled by Bifunctional Hydrogen Bonding under Microwave Irradiations

Abstract

Benzimidazol-amino thiazoles are synthesized under microwave irradiations using benzimidazole phenyl thiourea and 2-bromoacetophenone. Bifunctional hydrogen bonding plays an important role in chemical conversion. The reaction was carried out by C-C bond formation, followed by C-N bond cleavage and simultaneous migration of the benzimidazole ring. This reaction is novel and efficient for the synthesis of benzimidazol-amino thiazoles in which microwaves were used as driving forces. Synthesis of the product was controlled by double hydrogen bonding which is practically confirmed by the synthesis of routine imino-thiazole as an alternative product in the simple acidic condition. The simple acidic condition is neither responsible nor sufficient for optimum conversion of the benzimidazole migrated product. The synthesized products benzimidazole amino thiazoles <b>D4</b> (IC₅₀ = 4.207 μM) and <b>D8</b> (IC₅₀ = 2.398 μM) show interesting anticancer activities for human lung cancer with reference to doxorubicin (IC₅₀ = 1.750 μM).