Effect of structural modification on the inhibitory selectivity of rutaecarpine derivatives on human CYP1A1, CYP1A2, and CYP1B1

被引:65
作者
Don, MJ
Lewis, DFV
Wang, SY
Tsai, MW
Ueng, YF
机构
[1] Natl Res Inst Chinese Med, Taipei 112, Taiwan
[2] Univ Surrey, Sch Biomed & Life Sci, Guildford GU2 7XH, Surrey, England
关键词
D O I
10.1016/S0960-894X(03)00469-4
中图分类号
R914 [药物化学];
学科分类号
100701 [药物化学];
摘要
Derivatives of a CYP1A2 inhibitor rutaecarpine were synthesized to have potent and selective inhibition of human CYP1 members. Structural modelling shows a good fitting of rutaecarpine with the putative active site of human CYP1A2. Among the derivatives. 10- and 11-methoxyrutaecarpine are the most selective CYP1B1 inhibitors. 1-Methoxyrutaecarpine and 1,2-dimethoxyrutaecarpine are the most selective CYP1A2 inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2535 / 2538
页数:4
相关论文
共 21 条
[1]
STUDIES OF RUTAECARPINE AND RELATED QUINAZOLINOCARBOLINE ALKALOIDS [J].
BERGMAN, J ;
BERGMAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1246-1255
[2]
1-HYDROXYRUTAECARPINE FROM EUXYLOPHORA PARAENSIS [J].
DANIELI, B ;
PALMISAN.G ;
RAINOLDI, G ;
RUSSO, G .
PHYTOCHEMISTRY, 1974, 13 (08) :1603-1606
[3]
SYNTHESIS OF 2-(ALKYLAMINO)-5,6 AND 2-(ALKYLAMINO)-6,7-DIHYDROXY-3,4-DIHYDROQUINAZOLINES AND EVALUATION AS POTENTIAL DOPAMINE AGONISTS [J].
GROSSO, JA ;
NICHOLS, DE ;
KOHLI, JD ;
GLOCK, D .
JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (06) :703-708
[4]
Guengerich FP, 1995, CYTOCHROME P, P473
[5]
Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P4501B1 inhibitors [J].
Kim, S ;
Ko, H ;
Park, JE ;
Jung, S ;
Lee, SK ;
Chun, YJ .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (01) :160-164
[6]
Homology modelling of human CYP1A2 based on the CYP2C5 crystallographic template structure [J].
Lewis, DFV ;
Lake, BG ;
Dickins, M ;
Ueng, YF ;
Goldfarb, PS .
XENOBIOTICA, 2003, 33 (03) :239-254
[7]
Quantitative structure-activity relationships in substrates, inducers, and inhibitors of cytochrome P4501 (CYP1) [J].
Lewis, DFV .
DRUG METABOLISM REVIEWS, 1997, 29 (03) :589-650
[8]
Molecular modelling of CYP1 family enzymes CYP1A1, CYP1A2, CYP1A6 and CYP1B1 based on sequence homology with CYP102 [J].
Lewis, DFV ;
Lake, BG ;
George, SG ;
Dickins, M ;
Eddershaw, PJ ;
Tarbit, MH ;
Beresford, AP ;
Goldfarb, PS ;
Guengerich, FP .
TOXICOLOGY, 1999, 139 (1-2) :53-79
[9]
Lin L.C., 1991, J CHIN MED, V2, P94
[10]
A short synthesis of quinazolinocarboline alkaloids rutaecarpine, hortiacine, euxylophoricine A and euxylophoricine D from methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates [J].
Mohanta, PK ;
Kim, K .
TETRAHEDRON LETTERS, 2002, 43 (22) :3993-3996