Utility of pyrrole‐2‐thioacetohydrazide in synthesis of new heterocyclic compounds with promising antimicrobial activities and molecular docking studies

Abstract

AbstractOne‐pot synthetic method for [(3‐cyano‐5‐phenyl‐1H‐pyrrol‐2‐yl)sulfanyl]acetic acids 3a,b with excellent yield have been accomplished via a tetrabutylammonium bromide (TBAB) catalyzed reaction of mercaptoacetic acid with 2‐(2‐oxo‐2‐arylethyl) malononitrile under phase transfer catalysis conditions (PTC). The coupling of methyl [(3‐cyano‐5‐phenyl‐1H‐pyrrol‐2‐yl)sulfanyl] acetate 4a,b with hydrazine gave the corresponding 2‐[(3‐cyano‐5‐aryl‐1H‐pyrrol‐2yl)thio] acetohydrazides 5a,b, which reacted with glucose, acetylacetone, carbon disulfide, phenyl isothiocyanate, chloroacetyl chloride or benzaldehyde, to afford the compounds 6a,b–11a,b, respectively ranged from satisfactory to excellent yields. In vitro antibacterial and antifungal activities were assessed with good results. Furthermore, molecular docking experiments were done for the most active compounds against the E. coli MurB enzyme in order to determine the mechanism of their antibacterial activity and showed good binding interactions.