ALKYL ETHER DERIVATIVES OF THE FK-506 RELATED, IMMUNOSUPPRESSIVE MACROLIDE L-683,742 (C31-O-DESMETHYL ASCOMYCIN)

被引:8
作者
GOULET, MT [1 ]
HODKEY, DW [1 ]
STARUCH, MJ [1 ]
DUMONT, FJ [1 ]
LIN, S [1 ]
HUNG, SHY [1 ]
SIEKIERKA, JJ [1 ]
WYVRATT, MJ [1 ]
机构
[1] MERCK & CO INC,MERCK SHARP & DOHME RES LABS,DEPT IMMUNOL,RAHWAY,NJ 07065
关键词
D O I
10.1016/S0960-894X(01)80265-1
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Ether derivatives of the FK-506 related macrolide L-683,742 (C31-O-desmethyl ascomycin) have been prepared by alkylation with various alkyl 2,2,2-trichloroacetimidates. The in vitro immunosuppressive activity of these analogs is dependent both on the size and site of attachment (C31-O vs. C32-O) of the ether group.
引用
收藏
页码:927 / 930
页数:4
相关论文
共 14 条
[1]   MICROBIAL TRANSFORMATION OF IMMUNOSUPPRESSIVE COMPOUNDS .1. DESMETHYLATION OF FK506 AND IMMUNOMYCIN (FR-900520) BY ACTINOPLANES SP ATCC-53771 [J].
CHEN, TS ;
ARISON, BH ;
WICKER, LS ;
INAMINE, ES ;
MONAGHAN, RL .
JOURNAL OF ANTIBIOTICS, 1992, 45 (01) :118-123
[2]   IDENTIFICATION OF CALCINEURIN AS A KEY SIGNALING ENZYME IN LYMPHOCYTE-T ACTIVATION [J].
CLIPSTONE, NA ;
CRABTREE, GR .
NATURE, 1992, 357 (6380) :695-697
[3]  
DUMONT FJ, 1990, J IMMUNOL, V144, P251
[4]   CALCINEURIN PHOSPHATASE-ACTIVITY IN LYMPHOCYTES-T IS INHIBITED BY FK-506 AND CYCLOSPORINE-A [J].
FRUMAN, DA ;
KLEE, CB ;
BIERER, BE ;
BURAKOFF, SJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (09) :3686-3690
[5]  
GOULET MT, 1994, BIOMED CHEM LETT, V4
[6]   A RECEPTOR FOR THE IMMUNOSUPPRESSANT FK506 IS A CIS-TRANS PEPTIDYL-PROLYL ISOMERASE [J].
HARDING, MW ;
GALAT, A ;
UEHLING, DE ;
SCHREIBER, SL .
NATURE, 1989, 341 (6244) :758-760
[7]   BENZYL TRICHLOROACETIMIDATE, A VERSATILE REAGENT FOR ACID-CATALYZED BENZYLATION OF HYDROXY-GROUPS [J].
IVERSEN, T ;
BUNDLE, DR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (23) :1240-1241
[8]   CALCINEURIN IS A COMMON TARGET OF CYCLOPHILIN-CYCLOSPORINE-A AND FKBP-FK506 COMPLEXES [J].
LIU, J ;
FARMER, JD ;
LANE, WS ;
FRIEDMAN, J ;
WEISSMAN, I ;
SCHREIBER, SL .
CELL, 1991, 66 (04) :807-815
[9]   INHIBITION OF T-CELL SIGNALING BY IMMUNOPHILIN LIGAND COMPLEXES CORRELATES WITH LOSS OF CALCINEURIN PHOSPHATASE-ACTIVITY [J].
LIU, J ;
ALBERS, MW ;
WANDLESS, TJ ;
LUAN, S ;
ALBERG, DG ;
BELSHAW, PJ ;
COHEN, P ;
MACKINTOSH, C ;
KLEE, CB ;
SCHREIBER, SL .
BIOCHEMISTRY, 1992, 31 (16) :3896-3901
[10]   FK-506-SENSITIVE AND CSA-SENSITIVE ACTIVATION OF THE INTERLEUKIN-2 PROMOTER BY CALCINEURIN [J].
OKEEFE, SJ ;
TAMURA, J ;
KINCAID, RL ;
TOCCI, MJ ;
ONEILL, EA .
NATURE, 1992, 357 (6380) :692-694