Triazolylbenzimidazolthiones and derivatives of the new 1,2,3-triazolo[ 1,5-a][ 1,3,5]benzotriazepine heterocycle

✍ Scribed by Giuliana Biagi; Irene Giorgi; Oreste Livi; Antonio Nardi; Valerio Scartoni

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2002
• Tongue: English
• Weight: 50 KB
• Volume: 39
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570390628

✦ Synopsis

Abstract

Four new triazolylbenzimidazolthione derivatives (2a‐d), analogous to triazolylbenzimidazolone derivatives previously tested as activators of the BK~Ca~ potassium channels, were prepared and assayed without success. Some derivatives of a new tricyclic nitrogen heterocycle, 1,2,3‐triazolo[1,5‐a][1,3,5]benzo‐triazepine, bearing a carboxamido group in the 3 position, other substituents in the 8 position and a carbonyl (5a‐d) or thione (6a‐c) or methylthio (7a‐c) function in the 5 position were synthesised. The nucleophilic displacement of the methylthio substituent with morpholine or cyclopentylamine provided the 5‐amino‐substituted tricyclic derivatives 8a‐d. Starting from the l‐(2‐nitrophenyl)‐4‐cyano‐5‐amino‐1,2,3‐triazole (9), the 3‐cyano‐triazolobenzotriazepin‐5‐one derivative 12 was also obtained. The majority of the new compounds were tested towards the BK~Ca~ potassium channels, the benzodiazepine and adenosine A~1~ and A~2a~ receptors, but no remarkable activity was detected.