title: Synthesis and anticancer activity of (R,S)-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purines.
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.
authors.affiliation: Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, c/Campus de Cartuja s/n, 18071 Granada, Spain.
authors.forename: Mónica
authors.initials: M
authors.lastname: Díaz-Gavilán
authors.forename: Ana
authors.initials: A
authors.lastname: Conejo-García
authors.forename: Olga
authors.initials: O
authors.lastname: Cruz-López
authors.forename: María C
authors.initials: MC
authors.lastname: Núñez
authors.forename: Duane
authors.initials: D
authors.lastname: Choquesillo-Lazarte
authors.forename: Josefa M
authors.initials: JM
authors.lastname: González-Pérez
authors.forename: Fernando
authors.initials: F
authors.lastname: Rodríguez-Serrano
authors.forename: Juan A
authors.initials: JA
authors.lastname: Marchal
authors.forename: Antonia
authors.initials: A
authors.lastname: Aránega
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Gallo
authors.forename: Antonio
authors.initials: A
authors.lastname: Espinosa
authors.forename: Joaquín M
authors.initials: JM
authors.lastname: Campos
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology* / Q000627:therapeutic use; D001943:Breast Neoplasms / Q000188:drug therapy / Q000473:pathology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D018360:Crystallography, X-Ray; D005260:Female; D006571:Heterocyclic Compounds / Q000737:chemistry; D006801:Humans; D020128:Inhibitory Concentration 50; D009584:Nitrogen / Q000737:chemistry; D010075:Oxathiins / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use*; D011687:Purines / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D006571:Heterocyclic Compounds; D010075:Oxathiins; D011687:Purines; D009584:Nitrogen