Copper-free Sonogashira reaction using 7-chloro camptothecins

被引：21
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
来源：
TETRAHEDRON | 2006年 / 62卷 / 11期
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
    CORCORAN, RC
    BANG, SH
    [J]. 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
    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
    [J]. 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
    Du, W
    [J]. TETRAHEDRON, 2003, 59 (44) : 8649 - 8687
  • [8] Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals
    Du, W
    Kaskar, B
    Blumbergs, P
    Subramanian, PK
    Curran, DP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (03) : 451 - 458
  • [9] Molecular modeling studies of the DNA-topoisomerase I ternary cleavable complex with camptothecin
    Fan, Y
    Weinstein, JN
    Kohn, KW
    Shi, LM
    Pommier, Y
    [J]. 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
    Fukuyama, T
    Shinmen, M
    Nishitani, S
    Sato, M
    Ryu, I
    [J]. ORGANIC LETTERS, 2002, 4 (10) : 1691 - 1694
1234