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- Title
Synthesis of N‐Alkyl‐Carbazole Derivatives as 5‐HT<sub>7</sub>R Antagonists.
- Authors
Kim, Youngjae; Yeom, Miyoung; Lee, Soyeon; Tae, Jinsung; Kim, Hak Joong; Rhim, Hyewhon; Seong, Jihye; Choi, Kyung Il; Min, Sun‐Joon; Choo, Hyunah
- Abstract
We designed and synthesized a series of N‐alkyl‐carbazoles with different alkyl chains and amine moieties, and biological evaluation was performed to discover novel 5‐HT7R antagonists. Among 27 synthesized compounds, 20, 21, 23, and 24 showed excellent binding affinities to 5‐HT7R (Ki = 65, 64, 55, and 31 nM, respectively), and good selectivity profiles over other serotonin receptors. In functional assays, those compounds showed weak antagonistic activities against 5‐HT7R. In particular, the compound 24, 2‐(4‐(5‐(9H‐carbazol‐9‐yl)pentyl)piperazin‐1‐yl)phenol, could be considered as a potent and selective 5‐HT7R ligand with weak antagonistic effect. From the molecular docking study, the aromatic hydroxyl group in 24 was shown to play an important role in binding to 5‐HT7R through a hydrogen bonding interaction with Asp142 in the ligand binding pocket of 5‐HT7R.
- Subjects
CARBAZOLE derivatives; ALKYL group; AMINES; MOIETIES (Chemistry); ORGANIC synthesis
- Publication
Bulletin of the Korean Chemical Society, 2018, Vol 39, Issue 9, p1083
- ISSN
0253-2964
- Publication type
Article
- DOI
10.1002/bkcs.11555