|
KMID : 0043319980210020198
|
|
Archives of Pharmacal Research
1998 Volume.21 No. 2 p.198 ~ p.206
|
|
|
Synthesis and Evaluation of Antitumor Activity
|
|
Jin Guang Zhu
Song Gyu-Yong
Zheng Xiang-Guo
Kim Yong
Sok Dai-Eun
Ahn Byung-Zun
|
|
|
Abstract
|
|
|
|
Fourty eight derivatives of 2-(1-oxyalkyl)-1,4-dioxy-9,10-anthraquinone were synthesized, and their antitumor activity was evaluated. On the whole, 2-(1-hydroxyalkyl)-1,4-dihydroxy-9,10-anthraquinones (DHAQ=1,4-dihydroxy-9,10-anthraquinone) showed stronger cytotoxic activity against L1210 cells than 2-(l-hydroxyalkyl)-1,4-dimethoxy-9,10-anthraquinones(DMAQ =1,4-dimethoxy-9,10-anthraquinone), implying that free hydroxy groups at C-1 and C-4 of the anthraquinone structure are necessary for the cytotoxic activity. The bioactivity of 2-(lhydroxyalkyl)-DHAQ derivatives differed according to the size of alkyl group at C-1;while the elongation of alkyl group over 7 carbon atoms failed to enhance the bioactivity, the derivatives possessing alkyl moiety of 1-6 carbon atoms showed an increase in the cytotoxicity and the antitumor activity in Sarcoma-180; 2-hydroxymethyl-DHAQ (, /ml; T/C, 125%), 2-(1 -hydroxyethyl)-DHAQ(;, 2-(1-hydroxypropyl)-DHAQ (/ml; 135.1%), 2-(1-hydroxybutyl)-DHAQ (, 2-(1-hydroxypentyl)-DHAQ (). and 2-(1-hydroxyhexyl)-DHAQ (). Next, 2-(1-Hydroxyalkyl)-DHAQ derivatives were acetylated to produce 2-(1-acetoxyalkyl)-DHAQ analogues. Although the acetylation somewhat enhanced the cytotoxicity, but not the antitumor action. In addition, the presence of phenyl group at enhanced the cytotoxicity and the T/C value, compared to alkyl groups of same size; 2-(1-hydroxy-1-phenyl)-DHAQ (, , T/C, 137%).
|
|
|
KEYWORD
|
|
|
1,4-dihydroxy-9, 10-anthraquinone, synthesis, S-180 and L1210 cells, structure-actitivity relationship
|
|
|
FullTexts / Linksout information
|
|
|
|
|
|
Listed journal information
|
|
  
|
|