Anti-Mycobacterial N-(2-Arylethyl)quinolin-3-amines Inspired by Marine Sponge-Derived Alkaloid
-
Published:2022-12-08
Issue:24
Volume:27
Page:8701
-
ISSN:1420-3049
-
Container-title:Molecules
-
language:en
-
Short-container-title:Molecules
Author:
Mukomura Junya,
Nonaka Hiroki,
Sato Hiromasa,
Kishimoto Maho,
Arai MasayoshiORCID,
Kotoku Naoyuki
Abstract
The synthesis and evaluation of simplified analogs of marine sponge-derived alkaloid 3-(phenethylamino)demethyl(oxy)aaptamine were performed to develop novel anti-mycobacterial substances. Ring truncation of the tricyclic benzo[de][1,6]-naphthyridine skeleton effectively weakened the cytotoxicity of the natural product, and the resulting AC-ring analog exhibited good anti-mycobacterial activity. A structure–activity relationship (SAR) study, synthesizing and evaluating some analogs, demonstrated the specificity and importance of the N-(2-arylethyl)quinolin-3-amine skeleton as a promising scaffold for anti-mycobacterial lead compounds.
Funder
Research Support Project for Life Science and Drug Discovery (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED
Ritsumeikan University
Japan Society for the Promotion of Science (JSPS) to N.K.
JSPS to M.A.
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference33 articles.
1. HIV and Tuberculosis Coinfection: Inextricably Linked Liaison;Idemyor;J. Natl. Med. Assoc.,2007
2. World Health Organization (2021, November 10). Global Tuberculosis Report 2021. Available online: https://www.who.int/publications/i/item/9789240037021.
3. Nonreplicating Persistence of Mycobacteriun tuberculosis;Wayne;Annu. Rev. Microbiol.,2001
4. Oxygen Depletion-Induced Dormancy in Mycobacterium bovis BCG;Lim;J. Bacteriol.,1999
5. Oxygen depletion induced dormancy in Mycobacterium smegmatis;Dick;FEMS Microbiol. Lett.,1998