Discovery of tetrahydroisoquinoline derivatives as selective histone deacetylase 6 inhibitors with neurite outgrowth-promoting activities and neuroprotective activities.

Bibliographic Details
Title: Discovery of tetrahydroisoquinoline derivatives as selective histone deacetylase 6 inhibitors with neurite outgrowth-promoting activities and neuroprotective activities.
Authors: Liu S; Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, PR China., Dang B; Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, PR China., Kang Z; Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, PR China., Wei R; Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, PR China., Yang Z; College of Medicinal and Chemical Engineering, Shaanxi A&F Technology University, Yangling, Shannxi 712100, PR China., Guo X; College of Medicinal and Chemical Engineering, Shaanxi A&F Technology University, Yangling, Shannxi 712100, PR China., Shao F; College of Medicinal and Chemical Engineering, Shaanxi A&F Technology University, Yangling, Shannxi 712100, PR China., Li Z; Department of Student Affairs, The Second Affiliated Hospital of Xi'an Jiaotong University, Xi'an 710004, Shaanxi, PR China., Xing L; Guangxi Key Laboratory of Urban Water Environment, College of Chemistry and Environmental Engineering, Baise University, Baise 533000, PR China. Electronic address: 1094895479@qq.com., Hu J; College of Medicinal and Chemical Engineering, Shaanxi A&F Technology University, Yangling, Shannxi 712100, PR China. Electronic address: hujiadong@aliyun.com., Chen X; Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, PR China. Electronic address: chenxin1888@nwsuaf.edu.cn.
Source: Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2026 Jul; Vol. 136, pp. 130593. Date of Electronic Publication: 2026 Feb 17.
Publication Type: Journal Article
Language: English
Journal Info: Publisher: Elsevier Science Ltd Country of Publication: England NLM ID: 9107377 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1464-3405 (Electronic) Linking ISSN: 0960894X NLM ISO Abbreviation: Bioorg Med Chem Lett Subsets: MEDLINE
Imprint Name(s): Publication: Oxford : Elsevier Science Ltd
Original Publication: Oxford ; New York : Pergamon Press, c1991-
MeSH Terms: Histone Deacetylase Inhibitors*/pharmacology , Histone Deacetylase Inhibitors*/chemistry , Histone Deacetylase Inhibitors*/chemical synthesis , Neuroprotective Agents*/pharmacology , Neuroprotective Agents*/chemistry , Neuroprotective Agents*/chemical synthesis , Histone Deacetylase 6*/antagonists & inhibitors , Histone Deacetylase 6*/metabolism , Tetrahydroisoquinolines*/pharmacology , Tetrahydroisoquinolines*/chemistry , Tetrahydroisoquinolines*/chemical synthesis , Neuronal Outgrowth*/drug effects , Neurites*/drug effects , Drug Discovery*, Histone Deacetylases/metabolism ; Animals ; Rats ; Structure-Activity Relationship ; PC12 Cells ; Molecular Structure ; Humans ; Dose-Response Relationship, Drug
Abstract: Recently, histone deacetylase 6 (HDAC6) has attracted considerable attention for its potential in treating neurodegenerative disorders. In this paper, a series of tetrahydroisoquinoline derivatives were designed and synthesized as selective HDAC6 inhibitors. 4-((7-chloro-3, 4-dihydroisoquinolin-2(1H)-yl)methyl)-3-fluoro-N-hydroxybenzamide (8g), the most promising compound, potently inhibited HDAC6 (IC50 = 7.0 nM) and exhibited >2000 ~ fold selectivity over HDAC1. Molecular simulation indicated its molecular basis of HDAC6 inhibition. In vitro, 8g showed no significant toxicity on rat dopaminergic pheochromocytoma PC-12 cells. Furthermore, we demonstrated that 8g induced neurite outgrowth and showed good neuroprotective activity in PC-12 cells. Our research provided a new promising structure for the development of HDAC6is against Alzheimer's disease.
(Copyright © 2024. Published by Elsevier Ltd.)
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Contributed Indexing: Keywords: HDAC6 inhibitor; Neurite outgrowth; Neuroprotective; Selectivity; THIQ
Substance Nomenclature: 0 (Histone Deacetylase Inhibitors)
0 (Neuroprotective Agents)
EC 3.5.1.98 (Histone Deacetylase 6)
0 (Tetrahydroisoquinolines)
EC 3.5.1.98 (HDAC6 protein, human)
EC 3.5.1.98 (Histone Deacetylases)
Entry Date(s): Date Created: 20260219 Date Completed: 20260708 Latest Revision: 20260708
Update Code: 20260708
DOI: 10.1016/j.bmcl.2026.130593
PMID: 41713755
Database: MEDLINE
Description
ISSN:1464-3405
DOI:10.1016/j.bmcl.2026.130593