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Prins‐Type Synthesis and SAR Study of Cytotoxic Alkyl Chloro Dihydropyrans

AuthorsMiranda, Pedro O. ; Padrón, José M.; Padrón, Juan I. ; Villar, Jesús; Martín, Víctor S.
KeywordsAntitumor agents
Iron(III ) chloride
Organohalogen drugs
Prins reaction
Structure–activity relationship
Issue Date1-Mar-2006
CitationChemMedChem 1(3): 323-329 (2006)
AbstractA series of functionalized tetrahydropyran and dihydropyran derivatives was synthesized by means of a Prins‐type cyclization between unsaturated alcohols and several aldehydes. An unprecedented dimer bearing two 4‐chloro‐5,6‐dihydro‐2H ‐pyran scaffolds was obtained in high yield. A panel of three representative human solid tumor cells from diverse origin was used to assess the cytotoxicity of the compounds. Overall, the results show the relevance of the chlorovinyl group in the biological activity, and 2‐alkyl‐4‐chloro‐5,6‐dihydro‐2H ‐pyrans represent interesting leads for further chemical modifications and biological studies.
Publisher version (URL)https://doi.org/10.1002/cmdc.200500057
Appears in Collections:(IPNA) Artículos
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