Design, synthesis, and preliminary biological evaluation of novel ethyl 1-(2'-hydroxy-3'-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate.
We synthesized a series of novel small molecules, ethyl 1-(2'-hydroxy-3'-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate derivatives 3a-3o, by the reaction of ethyl 3-aryl-1H-pyrazole-5-carboxylate with 2-aryloxymethylepoxide in the presence of potassium carbonate at refluxing in acetonitrile in moderate or excellent yields. We investigated the effects of all the compounds on A549 cell growth. The results showed that 15 compounds could suppress A549 lung cancer cell growth. Among them, compound 3i was the most effective small molecule in inhibiting A549 cell growth. Compound 3f might most effectively induce A549 cell differentiation. Compound 3g remarkably induced cellular vacuolation.
Wei
Fang
F
Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China.
Zhao
Bao-Xiang
BX
Huang
Bin
B
Zhang
Lu
L
Sun
Chun-Hui
CH
Dong
Wen-Liang
WL
Shin
Dong-Soo
DS
Miao
Jun-Ying
JY
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D002455:Cell Division / Q000187:drug effects*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects*; D015195:Drug Design; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008175:Lung Neoplasms; D008958:Models, Molecular; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000970:Antineoplastic Agents; D004952:Esters; D011720:Pyrazoles