6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: asymmetric synthesis, and anti-proliferative properties.
(R)-Goniothalamin, is a member of styryl lactones, possesses selective cytotoxicity against cancer cell lines. In this work, replacement of styryl substituent with 2-naphthyl and 3-quinoyl gave new analogues which may have less conformational changes compared to the lead compound. Anti-proliferative tests indicated that 2-naphthyl substituted (R)-5,6-dihydro-2H-pyran-2-one has slightly better cytotoxicity than (R)-goniothalamin. To clarify the effect of 2-naphthyl substituent additional aryl substituted (R)-5,6-dihydro-2H-pyran-2-ones have been synthesized enantioselectively and tested against PC-3 and MCF-7 cell lines.
Kasaplar
Pinar
P
Izmir Institute of Technology, Faculty of Science, Department of Chemistry, Urla 35430, Izmir, Turkey.
Yilmazer
Ozgür
O
Cağir
Ali
A
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D007659:Ketones; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D011753:Pyrones / Q000737:chemistry; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D007659:Ketones; D011714:Pyrans; D011753:Pyrones; C103280:goniothalamin