Microwave prompted multigram synthesis, structural determination, and photo-antiproliferative activity of fluorinated 4-hydroxyquinolinones.
3-Unsubstituted 4-hydroxyquinolin-2(1H)-one containing F and CF(3) 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.
Arya
Kapil
K
Indian Oil Corporation Limited, Catalyst Division, R&D Centre, Faridabad, Haryana 121007, India. aryakapil2001@yahoo.com
Agarwal
Manish
M
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D049109:Cell Proliferation; D004354:Drug Screening Assays, Antitumor; D005461:Fluorine / Q000737:chemistry; D006801:Humans; D006912:Hydroxyquinolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D006912:Hydroxyquinolines; D017319:Photosensitizing Agents; D005461:Fluorine