Synthesis, structure, and bioactivity of N'-substituted benzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives.
Some 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives were synthesized by cyclization reaction of N'-substituted benzylidene-3,4,5-trimethoxybenzohydrazide in acetic anhydride. Their structures were verified by elemental analysis, IR, (1)H NMR, and (13)C NMR. Compound 3i was provided with X-ray crystallographic data. The compounds were evaluated for their antiproliferative activities against some cancer cells in vitro by MTT method. Among them, 2a, 2b, 2c, 2f, 3l, and 3m were highly effective against PC3 cells and 2a, 2c, and 2f showed moderate activities against Bcap37 and BGC823 cells. The IC(50) values of high active compounds 2a, 2b, 2c, 2f, 3l, and 3m against PC3 cells were 0.2, 1.8, 0.2, 1.2, 1.7, and 0.3muM, respectively.
Jin
Linhong
L
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, Guizhou 550025, PR China.
Chen
Jiang
J
Song
Baoan
B
Chen
Zhuo
Z
Yang
Song
S
Li
Qianzhu
Q
Hu
Deyu
D
Xu
Ruiqing
R
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001597:Benzylidene Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy / Q000473:pathology; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000091402:Prohibitins; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D001597:Benzylidene Compounds; D010069:Oxadiazoles; C000717331:PHB2 protein, human; D000091402:Prohibitins