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Molecules 2015, 20(9), 17675-17683;

Discovery and Structure-Based Optimization of 6-Bromotryptamine Derivatives as Potential 5-HT2A Receptor Antagonists

Laboratory of Marine Natural Products, School of Marine Sciences, Ningbo University, Ningbo 315211, China
College of Pharmacy, Jinan University, Guangzhou 510632, China
Collaborative Innovation Center for Zhejiang Marine High-efficiency and Healthy Aquaculture, Ningbo 315211, China
Key Laboratory of Applied Marine Biotechnology of Ministry of Education, Ningbo University, Ningbo 315211, China
Authors to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Received: 23 August 2015 / Revised: 17 September 2015 / Accepted: 21 September 2015 / Published: 23 September 2015
(This article belongs to the Section Natural Products Chemistry)
Full-Text   |   PDF [1182 KB, uploaded 23 September 2015]   |  


5-Hydroxytryptamine type 2A (5-HT2A) receptor is an important target for developing innovative antipsychotic agents in neuropsychiatric disorder therapies. To search for 5-HT2A receptor antagonists, a new indole alkaloid termed 6-bromo-N-propionyltryptamine (1), together with one known homologue 6-bromo-N-acetyltryptamine (2) were isolated and identified from a marine bacterium Pseudoalteromonas rubra QD1-2. Compound 1 with an N-propionyl side chain exhibited stronger 5-HT2A receptor antagonist activity than that of N-acetyl derivative (2), indicating that 6-bromotryptamine analogues with a longer chain acyl group perhaps displayed a more potent capacity to the target. Therefore, a series of new 6-bromotryptamine analogues (37) with different chain length of the acyl group (C4–C8) were prepared and evaluated activity against 5-HT2A receptor. Remarkably, 6-bromo-N-hexanoyltryptamine (5) displayed the most effective inhibitory activity, which was 5-fold stronger than that of the parent compound 1 and showed 70% efficacy of the positive control (ketanserin tartrate). View Full-Text
Keywords: 6-bromotryptamine; Pseudoalteromonas rubra; 5-HT2A receptor; antagonist 6-bromotryptamine; Pseudoalteromonas rubra; 5-HT2A receptor; antagonist

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Ding, L.; He, S.; Wu, W.; Jin, H.; Zhu, P.; Zhang, J.; Wang, T.; Yuan, Y.; Yan, X. Discovery and Structure-Based Optimization of 6-Bromotryptamine Derivatives as Potential 5-HT2A Receptor Antagonists. Molecules 2015, 20, 17675-17683.

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