Green and efficient three-component synthesis of novel isoniazid pyrazoles, molecular docking, antioxidant and antitubercular evaluation

Abstract

A series of novel isoniazid pyrazole derivatives were synthesized by an efficient, multicomponent reaction of various substituted aromatic aldehydes, isoniazid, and malononitrile in aqueous ethanol. The catalyst-free, green, three-component reaction took place well with good to excellent yields of the desired derivatives. The synthesized novel derivatives were screened for antimicrobial, antioxidant, and anti-TB properties along with the molecular docking study. Some of the synthesized compounds exhibit moderate antibacterial and comparable antifungal properties, while all of them display strong antioxidant activity. The compound 4l demonstrates the most significant activity against M. tuberculosis with MIC = 0.125 µg/mL. The various analytical techniques including FT-IR, 1H NMR, 13C NMR, and HRMS were utilized to confirm the structures of the newly synthesized compounds.