Copper-free Sonogashira reaction using 7-chloro camptothecins

被引:22
作者
Luo, Y
Gao, HY
Li, YF
Huang, WG
Lu, W
Zhang, ZG
机构
[1] Chinese Acad Sci, Grad Sch, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
关键词
camptothecin; topoisomerase; 1; Sonogashira coupling; palladium; catalysis;
D O I
10.1016/j.tet.2006.01.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We studied copper-free Sonogashira reaction using 7-chloro camptothecins, and determined that rac-BINAP/Pd(OAc)(2) was an efficient catalyst for the coupling reaction. With this process, a number of 7-substituted camptothecins with a wide range of functional groups are potentially accessible. Besides, two drugs, SN-38 and BNP-1350, Could be prepared by this method. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2465 / 2470
页数:6
相关论文
共 37 条
[1]  
BORN D, 2000, J MED CHEM, V43, P3970
[2]  
Boven E, 2000, ANN NY ACAD SCI, V922, P175
[3]  
CAREY FA, 1990, ADV ORGANIC CHEM STR, pCH12
[4]   IODOPYRIDINES FROM BROMOPYRIDINES AND CHLOROPYRIDINES [J].
CORCORAN, RC ;
BANG, SH .
TETRAHEDRON LETTERS, 1990, 31 (47) :6757-6758
[5]  
Dallavalle S, 2002, EXPERT OPIN THER PAT, V12, P837
[6]   Novel 7-oxyiminomethyl derivatives of camptothecin with potent in vitro and in vivo antitumor activity [J].
Dallavalle, S ;
Ferrari, A ;
Biasotti, B ;
Merlini, L ;
Penco, S ;
Gallo, G ;
Marzi, M ;
Tinti, MO ;
Martinelli, R ;
Pisano, C ;
Carminati, P ;
Carenini, N ;
Beretta, G ;
Perego, P ;
De Cesare, M ;
Pratesi, G ;
Zunino, F .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (20) :3264-3274
[7]   Towards new anticancer drugs: a decade of advances in synthesis of camptothecins and related alkaloids [J].
Du, W .
TETRAHEDRON, 2003, 59 (44) :8649-8687
[8]   Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals [J].
Du, W ;
Kaskar, B ;
Blumbergs, P ;
Subramanian, PK ;
Curran, DP .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (03) :451-458
[9]   Molecular modeling studies of the DNA-topoisomerase I ternary cleavable complex with camptothecin [J].
Fan, Y ;
Weinstein, JN ;
Kohn, KW ;
Shi, LM ;
Pommier, Y .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (13) :2216-2226
[10]   A copper-free Sonogashira coupling reaction in ionic liquids and its application to a microflow system for efficient catalyst recycling [J].
Fukuyama, T ;
Shinmen, M ;
Nishitani, S ;
Sato, M ;
Ryu, I .
ORGANIC LETTERS, 2002, 4 (10) :1691-1694