Synthesis, X-ray crystallographic analysis, and antitumor activity of N-(benzothiazole-2-yl)-1-(fluorophenyl)-O,O-dialkyl-alpha-aminophosphonates.
Alpha-aminophosphonates containing benzothiazole and fluorine moiety, 4a-4m, were synthesized by Mannich-type addition in ionic liquid media with high yield and short reaction time. Their structures were established by IR, (1)H NMR, (13)C NMR, and elemental analysis. The X-ray crystallographic data of compounds 4j and 4m were provided. The newly synthesized compounds were evaluated for their anticancer activities against PC3, A431, A375, and Bcap37 cells in vitro by the MTT method. Compound 4c is highly effective against PC3 cells and moderate to A431 cells. Hence, further study is necessary to find out the potential antitumor activities.
Jin
Linhong
L
Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, PR China.
Song
Baoan
B
Zhang
Guoping
G
Xu
Ruiqing
R
Zhang
Sumei
S
Gao
Xingwen
X
Hu
Deyu
D
Yang
Song
S
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D052160:Benzothiazoles; D049109:Cell Proliferation / Q000187:drug effects*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008175:Lung Neoplasms / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008545:Melanoma / Q000188:drug therapy; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000091402:Prohibitins; D011471:Prostatic Neoplasms / Q000188:drug therapy; D012878:Skin Neoplasms / Q000188:drug therapy; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D052160:Benzothiazoles; D063065:Organophosphonates; C000717331:PHB2 protein, human; D000091402:Prohibitins; D013844:Thiazoles; C005465:benzothiazole