Synthesis of N-Alkyl-Carbazole Derivatives as 5-HT7R Antagonists

Title
Synthesis of N-Alkyl-Carbazole Derivatives as 5-HT7R Antagonists
Author
민선준
Keywords
5-HT7 receptor; Antagonist; N-alkyl-carbazole; Serotonin; GPCR
Issue Date
2018-09
Publisher
WILEY-V C H VERLAG GMBH
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v. 39, No. 9, Page. 1083-1089
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 (K-i = 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.
URI
https://onlinelibrary.wiley.com/doi/full/10.1002/bkcs.11555http://repository.hanyang.ac.kr/handle/20.500.11754/106175
ISSN
1229-5949
DOI
10.1002/bkcs.11555
Appears in Collections:
COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY[E](과학기술융합대학) > CHEMICAL AND MOLECULAR ENGINEERING(화학분자공학과) > Articles
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