Studies on anthracenes. 2. Synthesis and cytotoxic evaluation of 9-acyloxy 1,8-dichloroanthracene derivatives.
The synthesis and cytotoxic evaluation of 9-acyloxy 1,8-dichloroanthracene derivatives are described. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 1,8-dichloro-9(10H)-anthracenone. Simple acylation of anthracenone occurred with appropriate acyl chlorides in CH2Cl2 with a catalytic amount of pyridine to give the 9-acyloxy-1,8-dichloroanthracene derivatives. Considerable interest has developed in the mechanism of how anthracenones achieve this desirable selectivity. These compounds were evaluated in vitro for their ability to inhibit the growth of human oral epidermoid carcinoma cells (KB cell line), human cervical carcinoma cells of ME 180 (GBM 8401) and Chinese hamster ovary (CHO) cells, respectively, as compared to mitoxantrone. The in vitro cytotoxicity evaluation of 9-acyloxy 1,8-dichloroanthracenes against these above cell lines revealed for most of the compounds a cytotoxic potency lower than that of mitoxantrone. The most active compounds were thus selected for further in vitro biological evaluation and structural modification.
Huang
H S
HS
School of Pharmacy, National Defense Medical Center, Taipei, Taiwan, ROC. huanghs@ndmctsgh.edu.tw
Chiu
H F
HF
Hwang
J M
JM
Jen
Y M
YM
Tao
C W
CW
Lee
K Y
KY
Lai
Y L
YL
D000818:Animals; D000873:Anthracenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology*; D016466:CHO Cells; D006224:Cricetinae; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007202:Indicators and Reagents; D007624:KB Cells; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D014407:Tumor Cells, Cultured
C450642:9-acyloxy 1,8-dichloroanthracene; D000873:Anthracenes; D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents