Synthesis of a novel class of non-peptide NK-2 receptor ligand, derived from 1-phenyl-3-pyrrol-1-ylindan-2-carboxamides.
A series of trans,trans-1-phenyl-3-pyrrol-1-ylindan-2-carboxamide derivatives has been synthesized in eight steps starting from cinnamic acid or 3,3-diphenylpropionic acid. The trans,trans configuration of these carboxamides has been established by X-ray analysis and by NOE experiments in NMR. These new compounds were evaluated for their potential NK-1, NK-2 and NK-3 receptors binding affinity. The N,N-disubstituted carboxamides bound selectively on NK-2 receptors.
Guillon
Jean
J
EA 2962-Pharmacochimie, UFR des Sciences Pharmaceutiques, Université Victor Segalen Bordeaux 2, 146, rue Léo Saignat, 33076 Cedex, Bordeaux, France.
Dallemagne
Patrick
P
Léger
Jean-Michel
JM
Sopkova
Jana
J
Bovy
Philippe R
PR
Jarry
Christian
C
Rault
Sylvain
S
D000577:Amides / Q000138:chemical synthesis / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D006801:Humans; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D064729:Neurokinin-1 Receptor Antagonists; D011869:Radioligand Assay; D018040:Receptors, Neurokinin-1 / Q000378:metabolism; D018041:Receptors, Neurokinin-2 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D018042:Receptors, Neurokinin-3 / Q000037:antagonists & inhibitors / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000577:Amides; D008024:Ligands; D064729:Neurokinin-1 Receptor Antagonists; D018040:Receptors, Neurokinin-1; D018041:Receptors, Neurokinin-2; D018042:Receptors, Neurokinin-3