Imidazo[2,1-b]thiazoles, imidazo[2,1-b]imidazoles and Pyrrolo[1,2-c]imidazoles. synthesis, structure and evaluation of benzodiazepine receptor binding

✍ Scribed by K. Kieć-Kononowicz; J. Handzlik; D. Lazewska; E. Pȩkala; C. E. Müller; J. Karolak-Wojciechowska

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2002
• Tongue: English
• Weight: 169 KB
• Volume: 39
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570390201

✦ Synopsis

Abstract

As a continuation of our studies on bicyclic heterocycles with benzodiazepine receptor affinity, derivatives with a 5:5 bicyclic skeleton, namely imidazo[2,1‐b]thiazoles, imidazo[2,1‐b]imidazoles and pyrrolo[1,2‐c]imidazoles were prepared. The compounds possessed an aromatic substituent with different spatial arrangement and distance to the bicyclic skeleton. X‐ray structure analysis was performed for Z‐2‐(4‐chlorobenzylidene)‐5,5‐diphenyl‐2,3,5,6‐tetrahydroimidazo[2,1‐b]imidazoline‐3,6‐dione (6a) and 5‐amino‐6‐cyano‐7‐phenyl‐1‐oxo‐3‐thioxo‐2,3‐dihydro‐1__H__‐pyrrolo[1,2‐c]imidazole (20a). In contrast to the previously described arylideneimidazo[2,1‐b]thiazepinones the smaller heterocyclic ring systems investigated in this study were devoid of meaningful benzodiazepine receptor affinity as well as anti‐convulsant activity.