Synthesis of chiral hydroxylated enones as potential anti-tumor agents

Tony Kung Ming Shing, Ho T. Wu, H. F. Kwok, Clara B.S. Lau

Research output: Contribution to journalArticle

4 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 languageEnglish
Pages (from-to)7562-7565
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number24
DOIs
Publication statusPublished - 2012 Dec 15
Externally publishedYes

Fingerprint

Ether
Tumors
Cells
Cytotoxicity
Neoplasms
Cell Line
HL-60 Cells
2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex- 2-enone
gabosine D

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

Cite this

Synthesis of chiral hydroxylated enones as potential anti-tumor agents. / Shing, Tony Kung Ming; Wu, Ho T.; Kwok, H. F.; Lau, Clara B.S.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 22, No. 24, 15.12.2012, p. 7562-7565.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Wu, Ho T. ; Kwok, H. F. ; Lau, Clara B.S. / Synthesis of chiral hydroxylated enones as potential anti-tumor agents. In: Bioorganic and Medicinal Chemistry Letters. 2012 ; Vol. 22, No. 24. pp. 7562-7565.
@article{22616dc2faef4e7b9d019085046cede1,
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 Kung Ming} and Wu, {Ho T.} and Kwok, {H. F.} and Lau, {Clara B.S.}",
year = "2012",
month = "12",
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 Limited",
number = "24",

}

TY - JOUR

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

AU - Shing, Tony Kung Ming

AU - Wu, Ho T.

AU - Kwok, H. F.

AU - Lau, Clara B.S.

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

UR - http://www.scopus.com/inward/record.url?scp=84870243591&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84870243591&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2012.10.026

DO - 10.1016/j.bmcl.2012.10.026

M3 - Article

C2 - 23102892

AN - SCOPUS:84870243591

VL - 22

SP - 7562

EP - 7565

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 24

ER -