Acta Cryst. (2007). E63, o3686-o3687  [ doi:10.1107/S1600536807033259 ]

14b-Chloro-4a-methoxy-3,3-dimethyl-2,3,4a,14b-tetrahydro-1H-benzo[a]pyrano[2,3-c]phenazine: a new active structural type against Mycobacterium tuberculosis

I. K. da C. Nunes, C. A. De Simone, R. S. F. Silva, A. V. Pinto and M. O. F. Goulart

Abstract: The title compound, C₂₂H₂₁ClN₂O₂, obtained from the reaction of the phenazine of -lapachone with trichloroisocyanuric acid, showed a minimum inhibitory concentration of 6.25 ng ml^-1 in tuberculostatic assays against Mycobacterium tuberculosis and established a new structural type with potential interest in medicinal chemistry. The dihydropyran ring adopts a pure chair conformation, while the ring fused to it has a half-chair conformation. The two substituents, OMe and Cl, are in axial positions, due to anomeric effects towards the methoxy derivative.

Online 3 August 2007

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