Synthesis and anticancer activity of (R,S)-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purines |
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Authors: | Díaz-Gavilán Mónica Conejo-García Ana Cruz-López Olga Núñez María C Choquesillo-Lazarte Duane González-Pérez Josefa M Rodríguez-Serrano Fernando Marchal Juan A Aránega Antonia Gallo Miguel A Espinosa Antonio Campos Joaquín M |
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Affiliation: | Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, c/Campus de Cartuja s/n, 18071 Granada, Spain. |
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Abstract: | A series of eleven 2- and 6-substituted (R,S)-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purine derivatives was obtained by applying a standard Mitsunobu protocol that led to a six-membered ring contraction from (R,S)-3,4-dihydro-2H-1,5-benzoxathiepin-3-ol via an episulfonium intermediate. The signal approximately delta=151 ppm, which corresponds to the C4' carbon atom, is unequivocal proof of the N9' regioisomer. The potential of the target molecules as anticancer agents is reflected in their activity against the MCF-7 cancer cell line. The most active compounds have IC(50) values of (6.18+/-1.70) and (8.97+/-0.83) microM. The results indicate that the anticancer activity for the most active compounds is correlated with their capacity to induce apoptosis. |
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Keywords: | antitumor compounds benzoxathiines microwave mitsunobu reaction nitrogen heterocycles |
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