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.11555https://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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