The Clitocybins and 2-Substituted-Isoindolin-1-Ones: Synthesis and in Vitro Antimycobacterial Activities

  • Amani Mejai Carthage University
  • Nambinina V. Rakotoarivelo Université de Toulouse
  • Ennaji Najahi Université de Toulouse III,
  • Pierre Perio bUniversité de Toulouse
  • Etienne Hollande INSERM UMR-1037, Université de Toulouse
  • Maria Rosalia Pasca University of Pavia, Dipartimento di Biologia e Biotecnologie
  • Rym Abidi Université Carthage, Faculté des sciences de Bizerte
  • Françoise Nepveu Université de Toulouse III,
Keywords: Isoindolinone, Tuberculosis, Clitocybins, Cytotoxicity, Antibiotics

Abstract

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).

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Author Biographies

Amani Mejai, Carthage University

Université Carthage, Faculté des sciences de Bizerte, LACReSNE, Interactions Moléculaires Spécifiques, Zarzouna-Bizerte,Tunis TN 7021,Tunisie.

Nambinina V. Rakotoarivelo , Université de Toulouse

Université de Toulouse III, UPS, PHARMA-DEV, UMR 152, 118 Route de Narbonne, F-31062 Toulouse cedex 9, France

Ennaji Najahi , Université de Toulouse III,

Université de Toulouse III, UPS, PHARMA-DEV, UMR 152, 118 Route de Narbonne, F-31062 Toulouse cedex 9, France.

Pierre Perio , bUniversité de Toulouse

IRD, UMR 152, F-31062 Toulouse cedex 9, France.

Etienne Hollande, INSERM UMR-1037, Université de Toulouse

INSERM UMR-1037, Université de Toulouse, Cancer Research Center of Toulouse (CRCT), Equipe Labellisée ligue contre le cancer and Laboratoire d’Excellence Toulouse Cancer (TOUCAN), Toulouse, France.

Maria Rosalia Pasca, University of Pavia, Dipartimento di Biologia e Biotecnologie

University of Pavia, Dipartimento di Biologia e Biotecnologie “Lazarro Spallanzani”, via Ferrata 1, 27100 Pavia, Italy.

Rym Abidi, Université Carthage, Faculté des sciences de Bizerte

Université Carthage, Faculté des sciences de Bizerte, LACReSNE, Interactions Moléculaires Spécifiques, Zarzouna-Bizerte,Tunis TN 7021,Tunisie.

Françoise Nepveu , Université de Toulouse III,

Université de Toulouse III, UPS, PHARMA-DEV, UMR 152, 118 Route de Narbonne, F-31062 Toulouse cedex 9, France.

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Published
2019-10-28
How to Cite
Mejai, A., Rakotoarivelo , N. V., Najahi , E., Perio , P., Hollande, E., Pasca, M. R., Abidi, R., & Nepveu , F. (2019). The Clitocybins and 2-Substituted-Isoindolin-1-Ones: Synthesis and in Vitro Antimycobacterial Activities. JOURNAL OF ADVANCES IN CHEMISTRY, 16, 5387-5394. https://doi.org/10.24297/jac.v16i0.8476
Section
Articles