Journal Article

The structure of a coumarin derivative related to the carcinogen benz[<i>a</i>]anthracene

Maria M. Flocco, H.L. Carrell, Ronald G. Harvey, David E. Zacharias and Jenny P. Glusker

in Carcinogenesis

Volume 17, issue 10, pages 2245-2248
Published in print October 1996 | ISSN: 0143-3334
Published online October 1996 | e-ISSN: 1460-2180 | DOI:
The structure of a coumarin derivative related to the carcinogen

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The three-dimensional structure of 3-methyl-2H-anthra-[l, 2-b]pyran-2-one, an anticarcinogenic coumarin related to the carcinogen benz[a]anthracene, has been determined by X-ray diffraction techniques. The molecule, apart from hydrogen atoms in the methyl group, is flat, the maximum deviation from its least squares best plane being 0.13 Å. The carbonyl C=O bond length is normal [1.206(1) Å] and the bonding throughout the molecule indicates localization of double bonds within the coumarin ring, but some delocalization of electrons in the other rings. Molecules pack in planes parallel to each other, the coumarin ring oxygen atom lying between two aromatic rings of other coumarin molecules. The bulky methyl groups are not involved in such stacking, while the carbonyl groups attract C-H groups in neighboring molecules by way of C-H...O interactions. These are the types of interactions that such coumarins could make if they bound to hydropobic areas in biological macromolecules.

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Subjects: Clinical Cytogenetics and Molecular Genetics

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