New generation dopaminergic agents. Part 8: heterocyclic bioisosteres that exploit the 7-OH-2-(aminomethyl)chroman D(2) template

Richard E Mewshaw; Rulin Zhao; Xiaojie Shi; Karen Marquis; Julie A Brennan; Hossein Mazandarani; Joseph Coupet; Terrance H Andree

doi:10.1016/s0960-894x(01)00778-8

New generation dopaminergic agents. Part 8: heterocyclic bioisosteres that exploit the 7-OH-2-(aminomethyl)chroman D(2) template

Bioorg Med Chem Lett. 2002 Feb 11;12(3):271-4. doi: 10.1016/s0960-894x(01)00778-8.

Authors

Richard E Mewshaw¹, Rulin Zhao, Xiaojie Shi, Karen Marquis, Julie A Brennan, Hossein Mazandarani, Joseph Coupet, Terrance H Andree

Affiliation

¹ Global Chemical Sciences Department, Wyeth-Ayerst Research Laboratories, PO Box 42528, Philadelphia, PA 19101-2528, USA. mewshar@war.wyeth.com

PMID: 11814775
DOI: 10.1016/s0960-894x(01)00778-8

Abstract

Based on the 7-OH-2-(aminomethyl)chroman dopamine D(2) template (2) is described the preparation and resolution of two bioisosteric analogues. The benzimidazol-2-one derivative (6) had similar affinity to the known indolone derivative (4).

MeSH terms

Benzopyrans / chemical synthesis
Benzopyrans / chemistry*
Dopamine Agonists / chemical synthesis
Dopamine Agonists / chemistry*
Models, Structural
Receptors, Dopamine D2 / administration & dosage
Receptors, Dopamine D2 / chemistry*
Structure-Activity Relationship
Templates, Genetic

Substances

2-(N-benzylaminomethyl)-7-hydroxybenzopyran
Benzopyrans
Dopamine Agonists
Receptors, Dopamine D2