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

研究成果: Article › 査読

7 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	7562-7565
ページ数	4
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	22
号	24
DOI	https://doi.org/10.1016/j.bmcl.2012.10.026
出版ステータス	Published - 2012 12月 15
外部発表	はい

UN SDG

この成果は、次の持続可能な開発目標に貢献しています

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ASJC Scopus subject areas

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

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10.1016/j.bmcl.2012.10.026

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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.",

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

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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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SN - 0960-894X

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Synthesis of chiral hydroxylated enones as potential anti-tumor agents

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UN SDG

ASJC Scopus subject areas

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