Synthesis and antiproliferative activity of (2R,3R)-disubstituted tetrahydropyrans. Part 2: Effect of side chain homologation.
In this study, we synthesized a series of enantiomerically pure (2R,3R)- and (2R,3S)-disubstituted tetrahydropyrans bearing a CH2O spacer group on the side chain at position 2 of the heterocyclic ring. The in vitro antiproliferative activities of the compounds were examined in the human solid tumor cell lines A2780 (ovarian cancer), SW1573 (non-small cell lung cancer), and WiDr (colon cancer). Overall, the results point out the relevance for antiproliferative activity of the distance between the heterocycle and the unsaturated group.
Carrillo
Romen
R
Instituto Universitario de Bio-Orgánica Antonio González (IUBO-AG), Universidad de La Laguna, C/Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain.
León
Leticia G
LG
Martín
Tomás
T
Martín
Víctor S
VS
Padrón
José M
JM
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007202:Indicators and Reagents; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D011714:Pyrans