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

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

7 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
Externally published	Yes

UN SDGs

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

SDG 3 Good Health and Well-being

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

Access to Document

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",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "24",

}

TY - JOUR

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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UR - https://www.scopus.com/pages/publications/84870243591#tab=citedBy

U2 - 10.1016/j.bmcl.2012.10.026

DO - 10.1016/j.bmcl.2012.10.026

M3 - Article

C2 - 23102892

AN - SCOPUS:84870243591

SN - 0960-894X

VL - 22

SP - 7562

EP - 7565

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 24

ER -

Synthesis of chiral hydroxylated enones as potential anti-tumor agents

Abstract

UN SDGs

Keywords

ASJC Scopus subject areas

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