Synthesis and Antitumor Activity Evaluation of C-3 (Rhodanine Unsaturated Ketone) Amides as Ofloxacin Derivatives
WANG Xue-meng1, LI Shu-ping2, YANG Tong1, HUANG Wen-long4, WANG Rui3*, HU Guo-qiang1*
1. Institute of Chemical Biology, Henan University,Kaifeng 475001, China; 2. Institute of Applied Technology for Pharmacy,Zhengzhou University of Industrial Technology,Zhengzhou 451150, China; 3. College of Nursing and Health, Henan University,Kaifeng 475001, China; 4. Centre of Drug Discovery,China Pharmaceutical University,Nanjing 210009, China
Abstract��OBJECTIVE To explore an efficient strategy for converting the antibacterial activity of fluoroquinolones to antitumor activity. METHODS An amide group as an isostere modified by rhodanine unsaturated ketone moiety corresponding to the C-3 carboxylic acid group resulted in 12 new title C-3 (5-arylidene-2-thioxo-1, 3-thiozolidin-2,4-dione-3-yl) amides (6a-6l) from ofloxacin 1. Their structures were characterized by elemental analysis and spectral data, and the in vitro antitumor activity of the title compounds against three tested cell lines was evaluated by MTT assay. RESULTS Twelve new title compounds were synthesized from ofloxacin and exhibited significantly higher potency than the parent compound ofloxacin. CONCLUSION Using a rhodanine unsaturated ketone hybrided amide group as the C-3 bioisostere is favorable to improve antitumor activity.
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WANG Xue-meng, LI Shu-ping, YANG Tong, HUANG Wen-long, WANG Rui, HU Guo-qiang. Synthesis and Antitumor Activity Evaluation of C-3 (Rhodanine Unsaturated Ketone) Amides as Ofloxacin Derivatives. Chinese Pharmaceutical Journal, 2018, 53(3): 174-177.
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2018, Vol. 53 
