title: Synthesis and biological evaluation as microtubule-active agents of several tetrahydrofuran and spiroacetal derivatives.
abstract: The stereoselective preparation of several molecules containing structural fragments of the tetrahydrofuran and spiroacetal type is described. Their degree of cytotoxicity and their interactions with tubulin have been investigated. It has been confirmed that the tetrahydrofuran derivatives are cytotoxic but, in contrast to previous reports, it has been found that the cytoxicity is not due to interactions with the microtubule network. Furthermore, and also in contrast to a previous report on closely related compounds, the spiroacetal derivatives do show interactions with tubulin, even though the precise mechanism and the binding site still remain to be established.
authors: Depart. de Q. Inorgánica y Orgánica, Univ. Jaume I, E-12071 Castellón, Spain.
authors: M
authors: M
authors: Carda
authors: J
authors: J
authors: Murga
authors: J
authors: J
authors: Paños
authors: C A
authors: CA
authors: Angulo-Pachón
authors: J
authors: J
authors: García-Pla
authors: S
authors: S
authors: Díaz-Oltra
authors: J A
authors: JA
authors: Marco
authors: C
authors: C
authors: Trigili
authors: M
authors: M
authors: Redondo-Horcajo
authors: J F
authors: JF
authors: Díaz
authors: I
authors: I
authors: Barasoain
mesh_terms: D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D002289:Carcinoma, Non-Small-Cell Lung / Q000188:drug therapy / Q000473:pathology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005260:Female; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D008168:Lung / Q000187:drug effects / Q000473:pathology; D008175:Lung Neoplasms / Q000188:drug therapy / Q000473:pathology; D008870:Microtubules / Q000187:drug effects / Q000378:metabolism / Q000473:pathology; D010051:Ovarian Neoplasms / Q000188:drug therapy / Q000473:pathology; D010053:Ovary / Q000187:drug effects / Q000473:pathology; D014404:Tubulin / Q000378:metabolism; D050257:Tubulin Modulators / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000080:Acetals; D000970:Antineoplastic Agents; D005663:Furans; D014404:Tubulin; D050257:Tubulin Modulators; C018674:tetrahydrofuran