[ Pharmaceutical Sciences Asia - ONLINE ]
E-ISSN 2586-8470
[ Journal Abbreviation: Pharm.Sci.Asia ]
Mahidol University Journal of Pharmaceutical Sciences
  FORMER NAME   "Mahidol University Journal of Pharmaceutical Sciences" Published Since 1974


DOI: https://doi.org/10.29090/psa.2017.04.227Pharm Sci Asia 2017; 44(4), 227-237

Synthesis and bioevaluation of new pyranophenothiazine derivatives

T.T. Nguyen1*, H. Dufat2, S. Michel2, S. Prado3, B. Saint-Joanis4, Y. Janin5

1 Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Ha Noi, Vietnam
2 Laboratoire de Pharmacognosie, UMR/CNRS 8638, Universite Paris Descartes, 75006 Paris, France
3 Molecules de Communication et Adaptation des Micro-organismes. FRE 3206 MNHN-CNRS Museum National dHistoire Naturelle. 57 rue Cuvier 75005 Paris, France
4 Unite de Genetique Moleculaire Bacterienne, Institut Pasteur, 28 rue du Docteur Roux, 75724 Paris Cedex 15, France
5 Laboratoire de Chimie Organique, URA 2128 CNRS-Institut Pasteur, 25-28 rue du Docteur Roux, 75724 Paris Cedex 15, France

Until now, tuberculosis is always a dangerous infectious disease. Because of the enlargement of multidrug-resistant strains (MDR-TB), the need of new drugs becomes more important. Fusing of 2 pharmacophores (phenothiazine and benzopyran), we intend to synthesize some new pyranophenothiazine derivatives, and evaluate their antituberculosis activities. The designed compounds were prepared using conventional synthetic methods with all PA chemical agents (from Merck, TCI, Sigma). The structure of all synthesized compounds had been confirmed by analysis of NMR and MS spectra. Antimycobacterial activity of the synthesized compounds on Mycobacterium bovis BCG (or on the virulent strain Mycobacterium tuberculosis H37Rv for the most promising compounds) had been determined using the Microdilution resazurin assay. Two compounds 8 and 9 were obtained by Claisen rearrangement of intermediate dimethylpropargyl ether. The sulfoxide and (+)cis-diol sulfoxide derivatives were obtained by oxydation, and the dihydro-derivatives - by reduction of the leader compounds. The anti-tuberculosis activities of 12 synthesized compounds were evaluated. Only the leading compound of linear structure (pyrano[b]phenothiazine) and two non-sulfoxide derivatives of angular structure (pyrano[a]phenothiazine) exhibited a mild inhibiting activity on the tested tuberculosis source. In conclusion, new pyrano-phenothiazine compounds have been prepared and bioevaluated. The results showed that three compounds exhibited a mild inhibiting activity on the tested tuberculosis source. These structural requirements will be taken into account for the design of further analogues in pyranophenothiazine series


pyranophenothiazine, chromene, antituberculosis, phenothiazine derivatives

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