Microwave prompted multigram synthesis, structural determination, and photo-antiproliferative activity of fluorinated 4-hydroxyquinolinones

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Abstract

3-Unsubstituted 4-hydroxyquinolin-2(1H)-one containing F and CF3 substituent in ring is important pharmacological and synthetic target and basic synthones for a number of antibacterial fluoroquinolones and is promising potent and selective glycine site NMDA receptors. A simple facile one-step microwave enhanced multigram synthesis of such fluorinated quinolones in reasonable purity has been developed in excellent yield (85–94%) in 3–5 min, whereas conventional synthesis required the harsh conditions, long reaction period with use of environmentally unacceptable regents giving the required product in lower yield. The phototoxicity as well as the cytotoxic activities of the title compounds are evaluated against leukemia- and adenocarcinoma-derived cell lines in comparison to the normal human keratinocytes. Structure–activity relationships between the chemical structures and the antimycobacterial, antifungal activity of the evaluated compounds are also discussed.

Graphical abstract

A simple facile one-step microwave enhanced multigram synthesis of such fluorinated quinolones in reasonable purity has been developed in excellent yield (85–94%) in 3–5 min and evaluated for photo-antiproliferative, antimicrobial, and antituberculosis activities.

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Acknowledgments

The authors wish to express their appreciation to Dr. André Loupy, Laboratoire des Réactions Sélectives Sur Supports, Université Paris-Sud, Orsay cedex, France, for his generous support and valuable suggestions. We are also thankful to Indian Oil Corporation, R&D Center, for spectral and financial supports and Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) for antimycobacterial data.

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