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 language | English (US) |
---|---|
Pages (from-to) | 4367-4377 |
Number of pages | 11 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 16 |
Issue number | 8 |
DOIs | |
State | Published - 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