Enantiospecific synthesis and cytotoxicity of 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one enantiomers.
An enantiospecific synthesis was developed to generate both enantiomers of 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one. A biological assay utilizing the HCT-116 colon cancer cell line to determine the cytotoxicity of these analogs revealed that only the (R)-enantiomer exhibited appreciable cytotoxicity with an IC(50) value of 0.2 microM.
Kimball
F Scott
FS
Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA.
Turunen
Brandon J
BJ
Ellis
Keith C
KC
Himes
Richard H
RH
Georg
Gunda I
GI
D002470:Cell Survival / Q000187:drug effects; D045325:HCT116 Cells; D006801:Humans; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C528985:7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one; D007212:Indolizines