New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities

Abstract

A new series of 3-substituted-2,1-benzisoxazoles (anthranils) were prepared by different methods and characterized by spectroscopic methods and mass spectrometry. These 2,1-benzisoxazoles were tested in vitro for their antiplasmodial activity on a chloroquine-resistant strain of Plasmodium falciparum (P.f.) (FcB1), and for antimicrobial activity against representative bacterial and fungal strains, as well as for cytotoxicity on MCF7 human breast cancer cells. Given the log Pcalc and selectivity index values (cytotoxicity/antiplasmodial activity ratio), the benzo[c]isoxazol-3-ylmethylene-phenyl-amine (11) (imino-benzisoxazole) was identified as the best hit against P.f. (FcB1), and the benzo[c]isoxazol-3-yl-phenyl-methanone (3) (3-acyl-2,1-benzisoxazole) against P.f. and the Geotrichum candidum fungal strain.

Keywords

• 2,1-Benzisoxazole
• Anthranil
• Antiplasmodial
• Antimicrobial