Open AccessThe Clitocybins and 2-Substituted-Isoindolin-1-Ones: Synthesis and in Vitro Antimycobacterial Activities
Author(s) -
Amani Mejai,
Nambinina V. Rakotoarivelo,
Ennaji Najahi,
Pierre Pério,
E Hollande,
Maria Rosalia Pasca,
Rym Abidi,
Françoise Nepveu
Publication year - 2019
Publication title -
journal of advances in chemistry
Language(s) - English
Resource type - Journals
ISSN - 2321-807X
DOI - 10.24297/jac.v16i0.8476
Subject(s) - antimycobacterial , in vitro , vero cell , chemistry , cytotoxicity , mycobacterium tuberculosis , stereochemistry , minimum inhibitory concentration , medicinal chemistry , tuberculosis , medicine , biochemistry , pathology
Despite strong indications of antimycobacterial activities for clitocybins reported since 1945, no reports linking chemical structure and activity have been reported in the literature since then. In this study, we synthesized some clitocybin derivatives (also called 2-substituted-isoindolinones), and tested their activities and carried out some chemical derivations. Isoindolinones were prepared from methyl 2-formyl-3,5-dimethoxybenzoate and various primary aromatic amines. Compounds were evaluated for in vitro activity against Mycobacterium tuberculosis H37Rv, as well as for cytotoxicity (CC50) on the Vero cell line. 4,6-dihydroxy-2-(4-hydroxyphenyl)isoindolin-1-one, 7, and 4-hydroxy-2-(4-hydroxyphenyl)-6-methoxy-isoindol-1-one, 5, exhibited the highest antimycobacterial activities (minimum inhibitory concentration = 19.45 µM and 18.45 µM, respectively) and were non-toxic (CC50 = 30 µM and 29 µM, respectively).