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

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Laboratory of Marine Natural Products, School of Marine Sciences, Ningbo University, Ningbo 315211, China
2
College of Pharmacy, Jinan University, Guangzhou 510632, China
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Collaborative Innovation Center for Zhejiang Marine High-efficiency and Healthy Aquaculture, Ningbo 315211, China
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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
Molecules 2015, 20(9), 17675-17683; https://doi.org/10.3390/molecules200917675
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)
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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MDPI and ACS Style

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. https://doi.org/10.3390/molecules200917675

AMA Style

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(9):17675-17683. https://doi.org/10.3390/molecules200917675

Chicago/Turabian Style

Ding, Lijian, Shan He, Wei Wu, Haixiao Jin, Peng Zhu, Jinrong Zhang, Tingting Wang, Ye Yuan, and Xiaojun Yan. 2015. "Discovery and Structure-Based Optimization of 6-Bromotryptamine Derivatives as Potential 5-HT2A Receptor Antagonists" Molecules 20, no. 9: 17675-17683. https://doi.org/10.3390/molecules200917675

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