Prins-type synthesis and SAR study of cytotoxic alkyl chloro dihydropyrans.
A 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.
Miranda
Pedro O
PO
Instituto Universitario de Bio-Orgánica Antonio González (IUBO-AG), Universidad de la Laguna, C/Astrofísico Francisco Sánchez, 2, 38206 La Laguna, and Instituto Canario de Investigación Biomédica, Hospital Universitario NS de Candelaria, Tenerife, Spain.
Padrón
José M
JM
Padrón
Juan I
JI
Villar
Jesús
J
Martín
Víctor S
VS
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D011714:Pyrans