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Design and synthesis of dual active neovibsanin derivatives based on a chemical structure merging method.

Authors :
Yanagimoto T
Kishimoto S
Kasai Y
Matsui N
Kubo M
Yamamoto H
Fukuyama Y
Imagawa H
Source :
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2020 Oct 15; Vol. 30 (20), pp. 127497. Date of Electronic Publication: 2020 Aug 12.
Publication Year :
2020

Abstract

A hybrid compound consisting of neovibsanin and trans-banglene was designed according to a structure merging method and synthesized via a sequence of key steps including a Diels-Alder cycloaddition, stereoselective alkynylation, and intramolecular oxa-Michael addition reaction. The biological activity of the synthetized acetal compound and its hemiacetal analogue was investigated in PC12 cells. These studies revealed that the designed hybrid compounds displayed neuritogenic activity. Furthermore, a relatively strong neurite outgrowth promoting activity was observed in the presence of NGF. These results suggest that the designed hybrid compound exhibited a dual activity.<br />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.<br /> (Copyright © 2020 Elsevier Ltd. All rights reserved.)

Details

Language :
English
ISSN :
1464-3405
Volume :
30
Issue :
20
Database :
MEDLINE
Journal :
Bioorganic & medicinal chemistry letters
Publication Type :
Academic Journal
Accession number :
32800919
Full Text :
https://doi.org/10.1016/j.bmcl.2020.127497