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

doi:10.1016/j.bmc.2008.02.073

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

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

13 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 language	English (US)
Pages (from-to)	4367-4377
Number of pages	11
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	8
DOIs	https://doi.org/10.1016/j.bmc.2008.02.073
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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2008.02.073

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

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.",

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AU - Kimball, F. Scott

AU - Turunen, Brandon J.

AU - Ellis, Keith C.

AU - Himes, Richard H.

AU - Georg, Gunda I.

N1 - 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

PY - 2008/4/15

Y1 - 2008/4/15

N2 - 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.

AB - 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.

KW - Colon cancer

KW - Enantiospecific synthesis

KW - HCT-116

KW - Tetrahydroindolizinones

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

Abstract

Bibliographical note

Keywords

UN SDGs

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