Abstract

BIGINELLI REACTION: COMPARATIVE STUDY OF FRUIT JUICES, OPTIMIZATION STRATEGIES, IN-SILICO ANALYSIS AND PHARMACOLOGICAL ACTIVITY

M. Hudgi, S. Santh, A. Awasthi, B. Mantripragada, D. Pingili*

Department of Pharmaceutical Chemistry, Sri Venkateshwara College of Pharmacy, Madhapur, Hyderabad 500081, Telangana, India.

ABSTRACT

This research article explores the influence of fruit juices on the efficiency of the biginelli reaction, a versatile multicomponent synthesis for diverse dihydropyrimidinones. A comparative analysis of fruit juices as green reaction media assessed their impact on reaction rates, yields, and selectivity. Biginelli reactions were carried out in fruit juices using equimolar mixture of thiourea /urea, ethyl acetoacetate and aromatic aldehyde under microwave irradiation. The reaction progressed within minutes, monitored by TLC, and confirmed through Proton NMR spectroscopy. Synthesized derivatives were evaluated for binding affinity towards protein (PDB ID: 1HD2) by molecular docking. Compounds 1a and 2a exhibited high yields, 81% and 71% respectively. Molecular docking revealed good binding affinity for compounds 2a, 1a, and 3a. Compound 2a demonstrated remarkable antioxidant activity with IC50 values; 4.18(μg/ml) and 2.54(μg/ml) for DPPH and Nitric oxide radical scavenging assays. Compound 2a could be considered as useful scaffold for further development to potent dihydropyrimidinone derivatives for enhanced antioxidant activity.

Keywords: Biginelli reaction; Dihydropyrimidinones; Anti-oxidant activity; Molecular docking; Proton NMR; Ethyl acetoacetate.