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Synthesis, characterization, crystal structure and cytotoxicity of 2,4-bis(selenomethyl) quinazoline

Título de la revista: STRUCTURAL CHEMISTRY
ISSN: 1040-0400
Volumen: 22
Número: 6
Páginas: 1233 - 1240
Fecha de publicación: 2011
Organoselenium compounds have already been reported to be good anticarcinogenic candidates. A new selenoquinazoline derivative, 2,4-bis(selenomethyl) quinazoline (compound 1), has been synthesized, spectroscopically characterized and its crystal structure has been studied. An intermolecular coupling between C(2) and H(5)' in the Heteronuclear Multiple Bond Correlation (HMBC) experiment has been observed. Assuming that the head-to-tail overlap of parallel molecules (as identified by X-ray diffraction) remains in solution to give bimolecular entities, the p-p interaction enables heteronuclear coupling between the former atoms with a three-bond distance [C(2)center dot center dot center dot(pi-pi)center dot center dot center dot C(5)'-H(5)']. The crystal structure of compound 1 has been solved by X-ray diffraction. It crystallizes in triclinic system, space group P-1. Unit cell parameters are a = 7.4969(7) angstrom, b = 8.7008(8) angstrom, c = 10.1666(9) angstrom, a = 110.215(2)degrees, beta = 90.354(2)degrees, gamma = 115.017(1)degrees. Linear chains in crystals of compound 1 are generated by C-H center dot center dot center dot Se and Se center dot center dot center dot Se bonds between molecules. Furthermore, head-to-tail overlap of parallel molecules, in which p-p interactions can occur, is observed. Compound 1 exhibited a cytotoxic effect in all of the evaluated tumoral cell lines and showed a higher cytotoxic effect in colon and breast cancer cell lines than etoposide, which was used as a reference compound.