Synthesis and binding affinities of 4-diarylaminotropanes, a new class of delta opioid agonists

被引：7

作者：

Boyd, RE ^{[1
]}

Carson, JR ^{[1
]}

Codd, EE ^{[1
]}

Gauthier, AD ^{[1
]}

Neilson, LA ^{[1
]}

Zhang, SP ^{[1
]}

机构：

[1] RW Johnson Pharmaceut Res Inst, Spring House, PA 19477 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2000年 / 10卷 / 10期

关键词：

D O I：

10.1016/S0960-894X(00)00182-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of 4-diarylaminotropanes has been prepared. Both endo and exo diastereomeric forms bound to the delta opioid receptor but the endo isomers were more potent and selective versus the mu opioid receptor than the exo isomers. The most potent delta opioid agonist (14) exhibited a delta opioid K-i of 0.2 nM and was 860-fold selective over mu. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1109 / 1111

页数：3

共 22 条

[1]

ALDRICH JV, 1996, BURGERS MED CHEM DRU, V3, P338

[2] Exploring the structure-activity relationships of [1-(4-tert-butyl-3′-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), a high-affinity and selective δ-opioid receptor nonpeptide agonist ligand [J].

Alfaro-Lopez, J ;

Okayama, T ;

Hosohata, K ;

Davis, P ;

Porreca, F ;

Yamamura, HI ;

Hruby, VJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (26) :5359-5368

[3] SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF ISOMERIC 3-PROPANANILIDOTROPANES [J].

BAGLEY, JR ;

RILEY, TN .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (04) :599-602

[4] Synthesis of novel analogues of the delta opioid ligand SNC-80 using AlCl3-promoted aminolysis [J].

Barn, DR ;

Bom, A ;

Cottney, J ;

Caulfield, WL ;

Morphy, JR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (09) :1329-1334

[5] CONFORMATION OF 3-ALPHA-PHENYL-3-BETA-TROPANYL PHENYL KETONE - A NOVEL NITROGEN-CARBONYL INTERACTION [J].

BELL, MR ;

ARCHER, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (01) :151-155

[6] Probes for narcotic receptor mediated phenomena .23. Synthesis, opioid receptor binding, and bioassay of the highly selective delta agonist (+)-4-[(alpha R)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide (SNC 80) and related novel nonpeptide delta opioid receptor ligands [J].

Calderon, SN ;

Rice, KC ;

Rothman, RB ;

Porreca, F ;

FlippenAnderson, JL ;

Kayakiri, H ;

Xu, H ;

Becketts, K ;

Smith, LE ;

Bilsky, EJ ;

Davis, P ;

Horvath, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (05) :695-704

[7]

CARSON JR, 1999, Patent No. 9933806

[8] CONFORMATIONAL-ANALYSIS OF TROPANE ANALOG OF PETHIDINE AND RELATED COMPOUNDS BY H-1 NMR-SPECTROSCOPY [J].

CASY, AF ;

COATES, JE .

ORGANIC MAGNETIC RESONANCE, 1974, 6 (08) :441-444

[9] OPIOID PROPERTIES OF SOME DERIVATIVES OF PETHIDINE BASED ON TROPANE [J].

CASY, AF ;

DEWAR, GH ;

PASCOE, RA .

JOURNAL OF PHARMACY AND PHARMACOLOGY, 1992, 44 (10) :787-790

[10]

CODD EE, 1995, J PHARMACOL EXP THER, V274, P1263

← 1 2 3 →