Synthesis and anti-proliferative activity of fluoroquinolone(rhodanine unsaturated ketone) amide derivatives
Author(s): GAO Liu-zhou, XIE Yu-suo, YAN Qiang, WU Shu-min, NI Li-li, ZHAO Hui, HUANG Wen-long, HU Guo-qiang, Institute of Chemistry and Biology, Henan University, Center of Drug Discovery, China Pharmaceutical University
Journal: Acta Pharmaceutica Sinica, Year 2015 , Issue 8 , Page 1008-1012
Keyword: fluoroquinolon-3-yl amide; rhodanine; unsaturated ketone; anti-cell proliferation activity;
Abstract: To discover novel antitumor rhodanine unsaturated ketones, a series of fluoroquinolone(rhodanine α, β-unsaturated ketone) amine derivatives(5a-5r) were designed and synthesized with fluoroquinolone amide scaffold as a carrier. The structures of eighteen title compounds were characterized by elemental analysis, 1H NMR and MS. The in vitro anti-proliferative activity against Hep-3B, Capan-1 and HL60 cells was evaluated by MTT assay. The results showed that the title compounds not only had more significant anti-proliferative activity against three tested cancer cell lines than that of the parent ciprofloxacin 1, but also exhibited the highest activity against Capan-1 cells. The SAR revealed that some compounds carrying aromatic heterocyclic rings or phenyl attached to an electron-withdrawing carboxyl or sulfonamide substituent were comparable to or better than comparison doxorubicin against Capan-1 cells. As such, it suggests that fluoroquinolone(rhodanine α, β-unsaturated ketone) amines are promising leads for the development of novel antitumor fluoroquinolones or rhodanine analogues.
http://caod.oriprobe.com/articles/46356287/Synthesis_and_anti_proliferative_activity_of_fluor.htm
Author(s): GAO Liu-zhou, XIE Yu-suo, YAN Qiang, WU Shu-min, NI Li-li, ZHAO Hui, HUANG Wen-long, HU Guo-qiang, Institute of Chemistry and Biology, Henan University, Center of Drug Discovery, China Pharmaceutical University
Journal: Acta Pharmaceutica Sinica, Year 2015 , Issue 8 , Page 1008-1012
Keyword: fluoroquinolon-3-yl amide; rhodanine; unsaturated ketone; anti-cell proliferation activity;
Abstract: To discover novel antitumor rhodanine unsaturated ketones, a series of fluoroquinolone(rhodanine α, β-unsaturated ketone) amine derivatives(5a-5r) were designed and synthesized with fluoroquinolone amide scaffold as a carrier. The structures of eighteen title compounds were characterized by elemental analysis, 1H NMR and MS. The in vitro anti-proliferative activity against Hep-3B, Capan-1 and HL60 cells was evaluated by MTT assay. The results showed that the title compounds not only had more significant anti-proliferative activity against three tested cancer cell lines than that of the parent ciprofloxacin 1, but also exhibited the highest activity against Capan-1 cells. The SAR revealed that some compounds carrying aromatic heterocyclic rings or phenyl attached to an electron-withdrawing carboxyl or sulfonamide substituent were comparable to or better than comparison doxorubicin against Capan-1 cells. As such, it suggests that fluoroquinolone(rhodanine α, β-unsaturated ketone) amines are promising leads for the development of novel antitumor fluoroquinolones or rhodanine analogues.
http://caod.oriprobe.com/articles/46356287/Synthesis_and_anti_proliferative_activity_of_fluor.htm
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