Synthesis of New 4-Heteroaryl-2-Phenylquinolines and Their Pharmacological Activity as NK-2/NK-3 Receptor Ligands

✍ Scribed by Anna Borioni; Carlo Mustazza; Isabella Sestili; Maria Sbraccia; Luciana Turchetto; Maria Rosaria Del Giudice

• Book ID: 102751374
• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 923 KB
• Volume: 340
• Category: Article
• ISSN: 0365-6233
• DOI: 10.1002/ardp.200600113

✦ Synopsis

Abstract

Substituted 4‐heteroaryl‐2‐phenylquinolines were synthesized and tested on NK‐2 and NK‐3 receptors in order to get a better insight in the structure‐activity relationship. On the whole, these molecules, which can be regarded as bioisosters of the NK‐3 antagonist SB 218795, displayed a lower activity than the template. Ring electronic distribution and H‐bond donor and acceptor positions played some role in selectivity, 2‐imidazolyl substituted 2a showing affinity mainly towards NK‐3 while 3‐pyrazolyl substituted 4 displayed a preferential interaction with NK‐2 receptor. Structural characterization of the synthesized compounds was achieved by NMR and mass techniques. Bidimensional ^1^H‐NOESY experiments were a helpful tool for the assignment of the isomeric structures of compounds 9 and 11b–c.