Antifungal and anthelmintic activity of novel benzofuran derivatives containing thiazolo benzimidazole nucleus: an in vitro evaluation

Abstract

A novel series of thiazolo[3,2-a]benzimidazole derivatives containing benzofuran nucleus (5a-l) have been synthesized. The key intermediate, substituted benzimidazolsulfanyl benzofuran ethanone (3a-d) was prepared by refluxing the mixture of substituted 2-acetyl benzofuran and substituted 2-mercaptobenzimidazole in acetic acid. The cyclisation of compounds (3a-d) using polyphosphoric acid furnished the corresponding 6-substituted benzofuran thiazolo[3,2-a]benzimidazoles (4a-d). Further, the cyclized compounds (4a-d) were subjected for Mannich reaction to give corresponding Mannich bases (5a-l). All newly synthesized compounds were screened for antifungal and anthelmintic activity. Amongst the tested compounds, 4b and 4d exhibited potential antifungal activity. From the anthelmintic activity data, it was found that the compounds 3a, 3b and 5i were found to be more effective against the tested earthworm Pheretima posthuma. In correlation to anthelmintic activity, the selected compounds were subjected for molecular docking studies and the compounds 3a and 5i have emerged as active anthelmintic agents with maximum binding affinity (−3.7 and −5.4 kcal/mol).

Synthesis and pharmacological screening of new isatin-3-[N2-(benzimidazol-1- acetyl)]hydrazone

“…It is reported that benzimidazole derivatives were active against Staphylococcus aureus, Escherichia coli, and Candida albicans [1]. Anthelmintic activities of few synthesized benzimidazole derivatives were also reported [2]. Further, in-vitro antiprotozoal activity of synthesized N-azopridinium salts and several betaines were reported adding to the existing pool of biological effects.…”

Design and synthesis of diethyl(substituted 2‐benzylbenzofuran‐3‐yl)phosphonates as antioxidant and antimicrobial agents

“…[22] Benzofurans are also a part of the molecular structure of a large number of natural products. [23] In recent time, benzofuran derivatives have valuable biological and pharmacological activities including enzyme inhibition, [24] antitubercular, antibacterial, [25] anticonvulsant, [26] anti-Alzheimer, [27] antimicrobial, anti-inflammatory, antioxidant, [28] antiprotozoal, [29] antihyperlipidemic, [30] anticancer, [31] anti-HIV, [32] antihypertensive, [33] analgesic, [34] antiparasitic, [35] antiplasmodial, [36] and antidiabetic. [37] Nanocrystalline metal oxides find excellent applications in the field of synthetic organic chemistry owing to their high catalytic activity, reusable nature, and benign character in the perspective of green chemistry.…”

“…Benzofurans are also a part of the molecular structure of a large number of natural products . In recent time, benzofuran derivatives have valuable biological and pharmacological activities including enzyme inhibition, antitubercular, antibacterial, anticonvulsant, anti‐Alzheimer, antimicrobial, anti‐inflammatory, antioxidant, antiprotozoal, antihyperlipidemic, anticancer, anti‐HIV, antihypertensive, analgesic, antiparasitic, antiplasmodial, and antidiabetic …”

Preparation and Biological Activities of New Heterocyclic Azo Ligand and Some of Its Chelate Complexes

“…The imidazole ring is found in very significant endogenous biomolecules, such as biotin, the autacoid histamine and the essential amino acid histidine [5]. Additionally, the imidazole derivatives are highly important in medicinal chemistry research; a lot of imidazole-containing compounds show biological activities such as antifungal, antibacterial, anti-inflammatory and anthelmintic [6], antitubercular [7], antiblood pressures, antiallergic, antiasthma [8] and anticancer [9]. Antipyrine is well known for its pharmaceutical as well as medical applications including antibacterial, antifungal [10], antituberculosis, anticancer [11], antitumor and antioxidant [12].…”