Studies on synthetic and structural characterization of new fluorine substituted phthalides of pharmaceutical interest

Abstract

An efficient and economical synthesis of some new fluorine substituted phthalides was accomplished from two γ-keto acids, 2-(4-fluorobenzoyl)benzoic acid and 2-(3,5-dinitro-4-flurobenzoyl)benzoic acid. Each acid was reacted with various phenolic compounds in presence of catalytic quantity of concentrated sulphuric acid to get the phthalides. The structures of the synthesized compounds were established on the basis of their elemental analysis, spectral data and chemical reactions. Some of the synthesized phthalides exhibited antibacterial and antifungal activity on antimicrobial screening against human pathogenic bacteria and fungi.

Keywords::

• Fluorine substituted phthalides
• phenols
• 2-(4- fluorobenzoyl)benzoic acid
• 2-(3,5-dinitro-4-flurobenzoyl)benzoic acid
• lactol
• sulphuric acid
• antibacterial activity
• antifungal activity

Acknowledgements

We are thankful to Dr. D. S. Rawat, Department of Chemistry, Delhi University, Delhi, India, for his generous help in recording the NMR spectra, and Dr. G. P. Pandey, Head and Scientist-G, Division of Organic Chemistry, National Chemical Laboratory, Pune, India, for providing mass spectral data. Support for antimicrobial evaluation by the NIH, NIAID, Division of AIDS, Grant No. AI 27094 and the USDA Agricultural Research Service Specific Cooperative Agreement No. 58-6408-2-0009 is gratefully acknowledged. We also sincerely thank Prof. Alice M. Clark and Marsha A. Wright (antimicrobial evaluation), University of Mississippi, Mississippi (USA), for providing generous help for the antimicrobial studies.

Declaration of interest

The authors report no conflicts of interest.