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 | |
| Publication status | Published - 2012 Dec 15 |
| Externally published | Yes |
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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 journal › Article
}
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 -