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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

✍ Scribed by Nunes, I. K. da C. ;De Simone, C. A. ;Silva, R. S. F. ;Pinto, A. V. ;Goulart, M. O. F.

Book ID
104491436
Publisher
International Union of Crystallography
Year
2007
Tongue
English
Weight
763 KB
Volume
63
Category
Article
ISSN
1600-5368

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✦ Synopsis

The title compound, C 22 H 21 ClN 2 O 2 , obtained from the reaction of the phenazine of -lapachone with trichloroisocyanuric acid, showed a minimum inhibitory concentration of 6.25 ng ml À1 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.

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