Enantiospecific synthesis and cytotoxicity of 7-(4-methoxyphenyl)-6-phenyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one enantiomers

F. Scott Kimball, Brandon J. Turunen, Keith C. Ellis, Richard H. Himes, Gunda I. Georg

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

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 IC50 value of 0.2 μM.

Original languageEnglish (US)
Pages (from-to)4367-4377
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number8
DOIs
StatePublished - Apr 15 2008

Bibliographical note

Funding Information:
These studies were supported by the National Cancer Institute (CA 90602 and N01-CM-67259). B.J.T. was supported by the Department of Defense Breast Cancer Predoctoral Fellowship (DAMD17-02-1-0435). We thank Deborah A. Bohlander for conducting the cytotoxicity assays and Dr. Dinah Dutta for the synthesis of (±)-tylophorine ( Table 1 ). 10

Keywords

  • Colon cancer
  • Enantiospecific synthesis
  • HCT-116
  • Tetrahydroindolizinones

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