Eco-sustainable synthesis and biological evaluation of 2-phenyl 1,3-benzodioxole derivatives as anticancer, DNA binding and antibacterial agents

Abstract

The current research and development scenario in medicinal chemistry demands small molecules synthesized in a simple, fast and effective way with enhanced activity and fewer side effects than the existing ones. Therefore, one-pot, microwave assisted green and efficient synthesis of a series of derivatives belonging to 2-phenyl 1,3-benzodioxole (1a–14a) and 2-phenyl 1,3-benzodioxole-4-ol (1b–14b) class were carried out and subsequently investigated for their anticancer, antibacterial and DNA binding potential. Compound 3c proved to be the most active one among the screened derivatives possessing anticancer and antibacterial potency greater than the standard reference compound (cisplatin and cinoxacin for anticancer and antibacterial activity, respectively). The most active compound in terms of DNA binding capacity was found to be 5b. A rewarding feature of the work is a facile, convenient, eco friendly one step synthesis of compounds demonstrating attenuated activity against cancer and bacterial cell with an inherent potential of binding to DNA. Subsequently, a hit molecule for further anticancer, antibacterial (compound 3c) and DNA binding studies (compound 5b) was also identified.

Keywords

• Benzodioxole
• Anticancer
• Antibacterial
• DNA binding
• Green chemistry