Synthesis and inhibitory evaluation of cyclohexen-2-yl- and cyclohexyl-substituted phenols and quinones to endothelial cell and cancer cells.
Alkylation of phenols with 1,3-cyclohexadiene (1) has been conducted and a series of cyclohexen-2-yl- and cyclohexyl-substituted phenols and quinones were screened against the proliferation of HUVEC and cancer cells. Phenol type as well as the size and occupied position of the substitute are important for the alkylating reaction and the inhibitory activity and selectivity of a compound. 2,5-di(cyclohexen-2-yl)benzene-1,4-diol (25) bearing two cyclohexen-2-yl groups and 2-tert-butyl-5-(cyclohexen-2-yl)benzene-1,4-diol (30) bearing cyclohexen-2-yl and tert-butyl groups exhibited good selectivity against HUVEC proliferation (IC50s of 2.0 and 1.4 microM, respectively) with relatively low toxicity to ccc-HPF-1.
Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou, Guangdong 510663, PR China.
Xin
X
Liu
Yingyong
Y
Ou
Shaopeng
S
Chen
Xin
X
Lu
Hao
H
Cheng
Xian
X
Jia
Decai
D
Wang
Guo-Chun
GC
Zhou
D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003510:Cyclohexanes / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry*; D042783:Endothelial Cells / Q000166:cytology / Q000187:drug effects*; D006801:Humans; D020128:Inhibitory Concentration 50; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D003510:Cyclohexanes; D053138:Cyclohexenes; D010636:Phenols; D011809:Quinones; C052568:cyclohexene; C506365:Cyclohexane; C034005:1,3-cyclohexadiene