Himbacine analogs as muscarinic receptor antagonists-effects of tether and heterocyclic variations

被引：11

作者：

Chackalamannil, S ^{[1
]}

Doller, D ^{[1
]}

McQuade, R ^{[1
]}

Ruperto, V ^{[1
]}

机构：

[1] Schering Plough Res Inst, Kenilworth, NJ 07033 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 15期

关键词：

D O I：

10.1016/j.bmcl.2004.05.047

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A number of analogs of the natural product himbacine were synthesized employing variations at the heterocyclic unit and the tether that links the heterocyclic unit to the tricyclic motif. Several of these analogs had M-2 affinity and M-1/M-2 selectivity comparable to those of himbacine. The structural and stereochemical requirements of the heterocyclic unit for muscarinic binding are discussed in the light of these data. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3967 / 3970

页数：4

共 25 条

[1] Studies towards a postulated biomimetic Diels-Alder reaction for the synthesis of himgravine
Baldwin, JE
Chesworth, R
Parker, JS
Russell, AT
[J]. TETRAHEDRON LETTERS, 1995, 36 (52) : 9551 - 9554
[2] BROWN RFC, 1956, AUST J CHEM, V9, P283
[3] ACYCLIC STEREOCONTROL WITH O-PROTECTED 2S-HYDROXY-PROPANAL - SOLVENT EFFECT
CAINELLI, G
GIACOMINI, D
PERCIACCANTE, F
TRERE, A
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (10) : 1913 - 1916
[4] CARRUTHERS V, 1990, TETRAHEDRON ORGANIC, V8, P269
[5] Total synthesis of (+)-himbacine and (+)-himbeline
Chackalamannil, S
Davies, RJ
Wang, Y
Asberom, T
Doller, D
Wong, J
Leone, D
McPhail, AT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) : 1932 - 1940
[6] Clader J W, 1999, Curr Opin Drug Discov Devel, V2, P311
[7] Design, synthesis, and structure-activity relationship studies of himbacine derived muscarinic receptor antagonists
Doller, D
Chackalamannil, S
Czarniecki, M
McQuade, R
Ruperto, V
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (06) : 901 - 906
[8] Doods Henri N., 1995, Drugs of the Future, V20, P157
[9] Synthesis and affinity studies of himbacine derived muscarinic receptor antagonists
Gao, LJ
Waelbroeck, M
Hofman, S
Van Haver, D
Milanesio, M
Viterbo, D
De Clercq, PJ
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (15) : 1909 - 1912
[10] Applications of organosulfur chemistry to organic synthesis: Total synthesis of (+)-himbeline and (+)-himbacine
Hart, DJ
Li, J
Wu, WL
Kozikowski, AP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (15) : 5023 - 5033

← 1 2 3 →