Chem. Pharm. Bull.

Chem. Pharm. Bull., 53(8),1062-1064, August 2005

Notes

Biological Evaluation of 2-Aryl-2-fluoropropionic Acids as Possible Platforms for New Medicinal Agents

Yoshio TAKEUCHI,^*^,a Hidehito FUJISAWA,^a Tomoya FUJIWARA,^a Mamoru MATSUURA,^b Hirotsugu KOMATSU,^b Satoshi UENO,^c and Takeshi MATSUZAKI^c

^a Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University; Sugitani 2630, Toyama 930-0194, Japan: ^b Pharmaceuticals Research Unit, Research & Development Division, Mitsubishi Pharma Corporation; 1000 Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan: and ^c Yakult Central Institute for Microbiological Research; 1796 Yaho, Kunitachi, Tokyo 186-8650, Japan. * To whom correspondence should be addressed. e-mail: takeuchi@ms.toyama-mpu.ac.jp

We investigated the cyclooxygenase (COX) inhibitory and anticancer activities of 2-aryl-2-fluoropropionic acids 1a-e. These fluorinated compounds showed lower inhibitory activity toward COX-1 than the corresponding non-fluorinated compounds 2a-e with retained inhibitory activity against COX-2 resulting in modification of the balance of COX-1/COX-2 inhibitions, and they showed little anticancer activity. Interesting differences of the activities between (S)- and (R)-enantiomers were observed in some cases.

Key words 2-aryl-2-fluoropropionic acid; non-steroidal anti-inflammatory drug; epimerization; chiral fluorinated structure

Notes

Biological Evaluation of 2-Aryl-2-fluoropropionic Acids as Possible Platforms for New Medicinal Agents

Yoshio TAKEUCHI,*,a Hidehito FUJISAWA,a Tomoya FUJIWARA,a Mamoru MATSUURA,b Hirotsugu KOMATSU,b Satoshi UENO,c and Takeshi MATSUZAKIc

Yoshio TAKEUCHI,^*^,a Hidehito FUJISAWA,^a Tomoya FUJIWARA,^a Mamoru MATSUURA,^b Hirotsugu KOMATSU,^b Satoshi UENO,^c and Takeshi MATSUZAKI^c