Design and Synthesis of (E)-4-(2-Phenyl-2H-chromen-3-yl)but-3-en-2-ones and Evaluation of their In Vitro Antimicrobial Activity

Letters in Organic Chemistry, 2015, 12, 1-7

Design and  Synthesis  of  (E)-4-(2-Phenyl-2H-chromen-3-yl)but-3-en-2-ones and Evaluation of their In Vitro Antimicrobial Activity

Sabita Nayak1,*, Subhendu Chakroborty1, Sujitlal Bhakta1, Pravati Panda1, Seetaram Mohapatra1, Sanjeet Kumar2, Padan Kumar Jena2 and Chandrasekhar Purohit3

1Department of Chemistry and 2Department of Botany, Ravenshaw University, Cuttack, Odisha, India; 3National Insti- tute of Science Education and Research, Bhubaneswar, Odisha, India

Received January 23, 2015: Revised March 10, 2015: Accepted March 25, 2015

Abstract: 2H-Chromene and its derivatives are an important class of organic compounds due to their wide range of bio- logical activities such as antimicrobial, antiviral, antiimflamatory and antitubercular agents. In the present work we have synthesized ten new 2H-chromene derivatives [(E)-4-(2-phenyl-2H-chromen-3-yl)but-3-en-2-one and its substituted ana- logues] following aldol condensation of 2H-chromene-3-carbaldehydes with acetone. These products have been character-ized by means of spectral data (1H, 13C, IR, Mass). The structure of one new compound (E)-4-(6,8-dichloro-2-phenyl-2H- chromen-3-yl)but-3-en-2-one was confirmed by X-ray analysis and the product was subsequently subjected to the in vitro evaluation of antimicrobial activity against two Gram positive bacteria Streptococcus mutans (MTCC 497) and Strepto- coccus pyogenes (MTCC 1926) and three Gram negative bacteria Vibrio cholera (MTCC 3909), Shigella flexneri (MTCC 1457) and Salmonella enteric typhi (MTCC 1252). The obtained results from in vitro antimicrobial assays by broth dilu- tion method indicated that many compounds under study exhibited excellent activity against all the microorganisms in comparison to standard kanamycin.