Novel 2,4,5-trisubstituted oxazole derivatives: synthesis and antiproliferative activity.
Microwave irradiation promotes the rapid O,N-acylation-cyclodehydration cascade reaction of oximes and acid chloride. Twenty novel 2,4,5-trisubstituted oxazole derivatives containing heterocycle moiety were synthesized and evaluated for their antiproliferative activity. The twenty compounds are all first reported and their structures were established by elemental analysis, (1)H NMR and (13)C NMR spectra. The bioassay tests showed that compounds 2-(2-(2-fluorophenyl)-4-(2,3,4-trimethoxyphenyl)oxazol-5-ylthio)benzo[d]thiazole (6af), 2-(2-(pyridin-3-yl)-4-(2,3,4-trimethoxyphenyl)oxazol-5-ylthio)pyrimidine (6bg) and 2-(2-(2-fluorophenyl)-4-(2,3,4-trimethoxyphenyl)oxazol-5-ylthio)-5-methyl-1,3,4-thiadiazole (6cf) displayed good antiproliferative activity in vitro, which were comparable to the positive control (5-fluorouracil).
State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China.
Xin-Hua
XH
Liu
Peng-Cheng
PC
Lv
Jia-Yu
JY
Xue
Bao-An
BA
Song
Hai-Liang
HL
Zhu
D002294:Carcinoma, Squamous Cell / Q000188:drug therapy; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008297:Male; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011471:Prostatic Neoplasms / Q000188:drug therapy; D013329:Structure-Activity Relationship
D010080:Oxazoles