Synthesis of chiral hydroxylated enones as potential anti-tumor agents

Tony K.M. Shing; Ho T. Wu; H. F. Kwok; Clara B.S. Lau

doi:10.1016/j.bmcl.2012.10.026

Synthesis of chiral hydroxylated enones as potential anti-tumor agents

Tony K.M. Shing, Ho T. Wu, H. F. Kwok, Clara B.S. Lau

Department of Chemistry

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

6 Citations (Scopus)

Abstract

A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines.

Original language	English
Pages (from-to)	7562-7565
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	24
DOIs	https://doi.org/10.1016/j.bmcl.2012.10.026
Publication status	Published - 2012 Dec 15

Keywords

Anti-tumor agents
COTC analogues
Hydroxylated enones
Selective cytotoxicity
Synthesis

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

UN SDGs

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

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10.1016/j.bmcl.2012.10.026

Cite this

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title = "Synthesis of chiral hydroxylated enones as potential anti-tumor agents",

abstract = "A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines.",

keywords = "Anti-tumor agents, COTC analogues, Hydroxylated enones, Selective cytotoxicity, Synthesis",

author = "Shing, {Tony K.M.} and Wu, {Ho T.} and Kwok, {H. F.} and Lau, {Clara B.S.}",

note = "Funding Information: This work was supported by a Strategic Investments Scheme administrated by the Center of Novel Functional Molecules, and by a Direct Grant, The Chinese University of Hong Kong.",

year = "2012",

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day = "15",

doi = "10.1016/j.bmcl.2012.10.026",

language = "English",

volume = "22",

pages = "7562--7565",

journal = "Bioorganic and Medicinal Chemistry Letters",

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publisher = "Elsevier Limited",

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T1 - Synthesis of chiral hydroxylated enones as potential anti-tumor agents

AU - Shing, Tony K.M.

AU - Wu, Ho T.

AU - Kwok, H. F.

AU - Lau, Clara B.S.

N1 - Funding Information: This work was supported by a Strategic Investments Scheme administrated by the Center of Novel Functional Molecules, and by a Direct Grant, The Chinese University of Hong Kong.

PY - 2012/12/15

Y1 - 2012/12/15

N2 - A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines.

AB - A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines.

KW - Anti-tumor agents

KW - COTC analogues

KW - Hydroxylated enones

KW - Selective cytotoxicity

KW - Synthesis

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 24

ER -

Synthesis of chiral hydroxylated enones as potential anti-tumor agents

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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