Abstract
As part of our program aimed at exploring the effect of introducing side chains to the anthracenone chromophore, we synthesized a novel series of 9-acyloxy 1,5-dichloroanthracene derivatives. Reduction of 1,5-dichloro anthraquinone with stannous chloride in boiling HCl and acetic acid with concomitant selective acylation led to the corresponding 9-acyloxy 1,5-dichloroanthracenes. These compounds were evaluated in vitro for their ability to inhibit the growth of human oral epidermoid carcinoma (KB) cells, human cervical carcinoma (GBM8401) cells and Chinese hamster ovary (CHO) cells, respectively. Compounds 3g, 3j and 3k were more potent against GBM cells than doxorubicin. Compounds 3j and 3v were more potent against KB cells than doxorubicin. Although compound 3j was active against both GBM and KB cells which was not cytotoxic to CHO cells. The implications of 9-acyloxy-1,5-dichloroanthracene analogs as potential anticancer agents are discussed.
| Original language | English |
|---|---|
| Pages (from-to) | 71-83 |
| Number of pages | 13 |
| Journal | Chinese Pharmaceutical Journal |
| Volume | 53 |
| Issue number | 2 |
| Publication status | Published - 2001 |
| Externally published | Yes |
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Keywords
- Acylation
- Anthracene
- Anthracenone
- Chromophore
- Cytotoxicity
ASJC Scopus subject areas
- Bioengineering
- Pharmaceutical Science
Cite this
Chromophore-modified antitumor anthracenes. 1. Cytotoxic activity of 9-acyloxy 1,5-dichloroanthracene analogues. / Huang, H. S.; Hwang, J. M.; Jen, Y. M.; Tao, C. W.; Lee, K. Y.; Shi, C. H.
In: Chinese Pharmaceutical Journal, Vol. 53, No. 2, 2001, p. 71-83.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Chromophore-modified antitumor anthracenes. 1. Cytotoxic activity of 9-acyloxy 1,5-dichloroanthracene analogues
AU - Huang, H. S.
AU - Hwang, J. M.
AU - Jen, Y. M.
AU - Tao, C. W.
AU - Lee, K. Y.
AU - Shi, C. H.
PY - 2001
Y1 - 2001
N2 - As part of our program aimed at exploring the effect of introducing side chains to the anthracenone chromophore, we synthesized a novel series of 9-acyloxy 1,5-dichloroanthracene derivatives. Reduction of 1,5-dichloro anthraquinone with stannous chloride in boiling HCl and acetic acid with concomitant selective acylation led to the corresponding 9-acyloxy 1,5-dichloroanthracenes. These compounds were evaluated in vitro for their ability to inhibit the growth of human oral epidermoid carcinoma (KB) cells, human cervical carcinoma (GBM8401) cells and Chinese hamster ovary (CHO) cells, respectively. Compounds 3g, 3j and 3k were more potent against GBM cells than doxorubicin. Compounds 3j and 3v were more potent against KB cells than doxorubicin. Although compound 3j was active against both GBM and KB cells which was not cytotoxic to CHO cells. The implications of 9-acyloxy-1,5-dichloroanthracene analogs as potential anticancer agents are discussed.
AB - As part of our program aimed at exploring the effect of introducing side chains to the anthracenone chromophore, we synthesized a novel series of 9-acyloxy 1,5-dichloroanthracene derivatives. Reduction of 1,5-dichloro anthraquinone with stannous chloride in boiling HCl and acetic acid with concomitant selective acylation led to the corresponding 9-acyloxy 1,5-dichloroanthracenes. These compounds were evaluated in vitro for their ability to inhibit the growth of human oral epidermoid carcinoma (KB) cells, human cervical carcinoma (GBM8401) cells and Chinese hamster ovary (CHO) cells, respectively. Compounds 3g, 3j and 3k were more potent against GBM cells than doxorubicin. Compounds 3j and 3v were more potent against KB cells than doxorubicin. Although compound 3j was active against both GBM and KB cells which was not cytotoxic to CHO cells. The implications of 9-acyloxy-1,5-dichloroanthracene analogs as potential anticancer agents are discussed.
KW - Acylation
KW - Anthracene
KW - Anthracenone
KW - Chromophore
KW - Cytotoxicity
UR - http://www.scopus.com/inward/record.url?scp=0034851868&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0034851868&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0034851868
VL - 53
SP - 71
EP - 83
JO - Taiwan Pharmaceutical Journal
JF - Taiwan Pharmaceutical Journal
SN - 1016-1015
IS - 2
ER -