Cu (Ι) catalyzed A³ cascade coupling via C‐H functionalization followed by cyclization: Synthesis, in silico, in vitro, and toxicity studies of imidazo[2,1‐b]thiazoles

Abstract

An influential method for the synthesis of imidazo[2,1-b]thiazoles via copper (I) catalysis was advanced through a multicomponent coupling of pharmacological scaffolds involving 2-aminothiazolyl-coumarin, benzaldehyde, and phenyl acetylene, a concealed variation. The protocol allows the establishment of highly efficient and user-friendly catalytic system for the A 3 cascade coupling; also, an environmentally benign, economical, and readily obtainable CuSO 4 / sodium ascorbate is portrayed. A sequence of 15 novel imidazo[2,1-b]thiazoles (7j-x) were synthesized and evaluated for their in vitro antimicrobial activity, in silico studies, and oral toxicity studies. The in vitro antifungal and antibacterial screening of synthesized compounds manifested favorable activity and disclosed that all these previously unknown compounds showed significant activity. Amid them, compound 7u portrayed the most effective inhibitory activity.

Microwave-assisted copper(i) catalyzed A3 cascade coupling of imidazo[1,2-a]pyridines via C–H bond functionalization as selective COX-2 inhibitors and antioxidants, and in silico studies

“…12 Nitrogen-comprising heterocycles have gained innumerable considerations owing to their occurrence in several natural products and synthetic compounds with interesting biological properties. [13][14][15] In particular, imidazo [1,2-a]azine and quinoline cores have drawn significant attention in medicinal chemistry due to their broad spectrum of pharmacological activities such as antibacterial, antifungal, antineoplastic, anti-inflammatory, 16 antidiabetic, antitumor, anxiolytic (Alpidem), hypnotic (Zolpidem), immunomodulatory (Kifunensine), antiulcer (Zolmidine), sedative (Necopidem and Saripidem) and anti-HIV (GSK812397) activities as shown in Fig. 1.…”