New thiazolyl-coumarin hybrids: Design, synthesis, characterization, X-ray crystal structure, antibacterial and antiviral evaluation

Abstract

A series of thiazole containing coumarin derivatives (2a-o) were efficiently synthesized as pharmacophore hybrids through Hantzsch cyclisation of 3-(2-bromoacetyl)-2H-chrome-2-ones with different N-substituted thiourea/N,N-di-substituted thiourea. All the synthesized compounds were evaluated for their potential as antibacterial, anti-tubercular and antiviral agents and some of the compounds displayed considerable potency against these strains. The presence of 2-bromophenylamino (2h) and 3,4-dichlorophenylamino (2g) group at thiazole moiety resulted the highest antibacterial (MIC 73 μM) and antitubercular (MIC 60 μM) activities, respectively. Antiviral screening displayed that methylamino derivative (2a) strongly inhibited the replication of H1N1 influenza A virus (IC50 value 4.84). Results of molecular docking studies also suggest that thiazolyl-coumarins could be an important scaffold for the design and development of novel antiviral agents.