Monomethoxytrityl (MMT) as a versatile amino protecting group for complex prodrugs of anticancer compounds sensitive to strong acids, bases and nucleophiles

被引：24
作者：
Dubowchik, GM
Radia, S
机构：
[1] Bristol-Myers Squibb Pharmaceut. R., Wallingford, CT 06492-7660
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 30期
关键词：
D O I：
10.1016/S0040-4039(97)01158-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cathepsin B-sensitive maleimidocaproyl-Phe-Lys linker compounds containing acid-sensitive anticancer drugs doxorubicin, mitomycin C and paclitaxel (taxol(R)) attached through a self-immolative p-aminobenzylcarbonyl spacer were prepared using monomethoxytrityl (MMT) as the amino protecting group for Lys. MMT could be removed cleanly and in high yield by dichloroacetic and chloroacetic acids in the presence of anisole with minimal workup. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：5257 / 5260
页数：4
相关论文
共 9 条
[1]   EFFICIENT ONE-POT SYNTHESIS OF N-TRITYL AMINO-ACIDS [J].
BARLOS, K ;
PAPAIOANNOU, D ;
THEODOROPOULOS, D .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1324-1326
[2]   A NOVEL CONNECTOR LINKAGE APPLICABLE IN PRODRUG DESIGN [J].
CARL, PL ;
CHAKRAVARTY, PK ;
KATZENELLENBOGEN, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (05) :479-480
[3]   THE PREPARATION AND SYNTHETIC APPLICATION OF HETEROBIFUNCTIONAL BIOCOMPATIBLE SPACER ARMS [J].
COOK, RM ;
ADAMS, JH ;
HUDSON, D .
TETRAHEDRON LETTERS, 1994, 35 (37) :6777-6780
[4]  
DUBOWCHIK GM, UNPUB
[5]  
GEORG GI, 1995, TAXOL R SCI APPL, P365
[6]  
GREEN TW, 1991, PROTECTIVE GROUPS OR
[7]   CURE OF XENOGRAFTED HUMAN CARCINOMAS BY BR96-DOXORUBICIN IMMUNOCONJUGATES [J].
TRAIL, PA ;
WILLNER, D ;
LASCH, SJ ;
HENDERSON, AJ ;
HOFSTEAD, S ;
CASAZZA, AM ;
FIRESTONE, RA ;
HELLSTROM, I ;
HELLSTROM, KE .
SCIENCE, 1993, 261 (5118) :212-215
[8]  
VYAS DM, 1995, CHEM PHARM TAXOL ITS, P110
[9]   THE SYNTHESIS OF POLYAMIDE NUCLEIC-ACIDS USING A NOVEL MONOMETHOXYTRITYL PROTECTING-GROUP STRATEGY [J].
WILL, DW ;
LANGNER, D ;
KNOLLE, J ;
UHLMANN, E .
TETRAHEDRON, 1995, 51 (44) :12069-12082
1