Journal of the Chemical Society. Perkin transactions I p. 2309 - 2313 (1996)
Update date:2022-07-30
Topics:
Komuro, Masakatsu
Higuchi, Tsunehiko
Hirobe, Masaaki
The oxidative hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids by a chemical cytochrome P-450 model and rat liver microsomal systems has been investigated. In the chemical system using meso-tetrakis(2,6-dichlorophenyl)porphyrin iron chloride [Fe(TDClPP)Cl] with iodosylbenzene (PhIO), γ,δ-unsaturated carboxylic acids have been converted into δ-hydroxy-γ-lactones in high yield and with high stereoselectivity. As an example of a β,γ-unsaturated carboxylic acid, indomethacin has been converted into the corresponding β-hydroxy γ-lactone. Several experiments directed toward mechanistic elucidation of the lactonization exclude a mechanism occurring via an epoxide intermediate. The products have been used as standards to identify the metabolites in the microsomal oxidation. In the case of indomethacin, the γ-lactone form is detected as a metabolite in the rat liver microsomal system, in a yield of 1.33%; the yield is significantly decreased in the presence of 2-diethylaminoethyl-2,2-diphenylvalerate hydrochloride (SKF-525A) and under a mixed CO-O2 (4:1) atmosphere. Thus, these metabolites are considered to be formed by a cytochrome P-450-dependent reaction.
View MoreHangzhou LINGEBA Technology Co., Ltd.
Contact:+0086-571-87389059
Address:Office 1-913,NewYouth Plaza, GongShu Area, HangZhou,ZheJiang,P.R.China
Huaihua Baohua Biotechnology Co.,Ltd
website:http://www.baochengchem.com
Contact:86-519-82698291
Address:HouYang chemical development zone,Jintan,Jiangsu,China (213200)
Zhejiang Allied Chemical Co.,Ltd
Contact:18967038207
Address:Area A-30, High-tech Industrial Park, Quzhou, Zhejiang, China.
Contact:+86-10-83993285
Address:Rm.1708, Haobai Tower, Building 6, No.50, North Road, West Third Ring, Haidian District, Beijing, China
Beyond Pharmaceutical Co., Ltd
Contact:+86-571-8195-3185
Address:No. 13-1, Liansheng Road, Yuhang District
Doi:10.1021/ol9910520
(1999)Doi:10.1002/asia.201300938
(2013)Doi:10.1021/jm970840x
(1998)Doi:10.3987/COM-92-S(T)89
(1993)Doi:10.1039/j39690002376
(1969)Doi:10.1016/S0040-4039(99)01694-9
(1999)
