Synthesis, absolute configuration, conformational analysis and binding affinity properties of enantiomeric forms of DAU 5750, a novel M1-M3 muscarinic receptor antagonist

M Turconi; A Gozzo; G Schiavi; G Fronza; A Mele; P Bravo

doi:10.1016/s0968-0896(00)82089-1

Synthesis, absolute configuration, conformational analysis and binding affinity properties of enantiomeric forms of DAU 5750, a novel M1-M3 muscarinic receptor antagonist

Bioorg Med Chem. 1994 Dec;2(12):1375-83. doi: 10.1016/s0968-0896(00)82089-1.

Authors

M Turconi¹, A Gozzo, G Schiavi, G Fronza, A Mele, P Bravo

Affiliation

¹ Department of Medicinal Chemistry, Boehringer Ingelheim Italia S.p.A., Milan.

PMID: 7788300
DOI: 10.1016/s0968-0896(00)82089-1

Abstract

Both the enantiomeric forms of DAU 5750, a novel muscarinic receptor antagonist, have been synthesized in order to assess the relevance of configurational/conformational features for high affinity binding to muscarinic receptor subtypes. The attribution of absolute stereochemistry and conformational analysis by means of molecular modelling and NMR techniques are also reported.

MeSH terms

Chymotrypsin / metabolism
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Muscarinic Antagonists / chemical synthesis*
Muscarinic Antagonists / chemistry
Muscarinic Antagonists / metabolism
Quinolines / chemical synthesis*
Quinolines / chemistry
Quinolines / metabolism
Receptors, Muscarinic / metabolism*
Stereoisomerism
Tropanes / chemical synthesis*
Tropanes / chemistry
Tropanes / metabolism

Substances

Muscarinic Antagonists
Quinolines
Receptors, Muscarinic
Tropanes
DAU 5750
Chymotrypsin