US EPA

7160146 

Journal Article 

Synthesis and biological evaluation of 3-(4-fluorophenyl)-1H-pyrazole derivatives as androgen receptor antagonists 

Guo, G; Liu, J; Wang, G; Zhang, D; Lu, J; Zhao, G; , 

2016 

Yes 

Anti-Cancer Drugs
ISSN: 0959-4973 

LIPPINCOTT WILLIAMS & WILKINS 

PHILADELPHIA 

27 

4 

278-285 

English 

26633887 

10.1097/CAD.0000000000000322 

WOS:000373774900002 

http://://WOS:000373774900002
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A novel series of 3-(4-fluorophenyl)-1H-pyrazole derivatives were synthesized and evaluated for their antiproliferative activity against two prostate cancer cell lines (LNCaP and PC-3) and androgen receptor target gene prostate-specific antigen (PSA) inhibitory activity in LNCaP cells. Several compounds showed potent antiproliferative activity against LNCaP cells and showed a promising PSA downregulation rate. Among these, compound 10e selectively inhibited LNCaP cell growth with an IC50 value of 18 mu mol/l and showed a PSA downregulation rate of 46%, which was better than the lead compound T3. 

Androgen receptor; Antagonist; Prostate cancer; Pyrazole derivatives; 3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 amine; 3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 carboxylic acid; 3 bromo 4 fluoro n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]aniline; 3 bromo n [3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]benzamide; 3 bromo n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl] 2 methylaniline; 3 bromo n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]aniline; 3 chloro 2 fluoro n [[3 (4 fluorophenyl) 1 methyl 1h pyrazol 5 yl]methyl]aniline; 3 chloro 4 fluoro n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]aniline; 3 chloro n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]aniline; 3 [[[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]amino]benzonitrile; 4 bromo n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]aniline; 4 chloro n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl] 3 (trifluoromethyl)aniline; 4 chloro n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]aniline; 4 fluoro n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]aniline; 4 [[[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]amino]benzonitrile; 4 [[[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl]amino]phthalonitrile; 5 (chloromethyl) 3 (4 fluorophenyl) 1 methyl 1h pyrazole; androgen receptor antagonist; antineoplastic agent; enzalutamide; ethyl 3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 carboxylate; ethyl 3 (4 fluorophenyl) 1h pyrazole 5 carboxylate; ethyl 4 (4 fluorophenyl) 2 hydroxy 4 oxobut 2 enoate; ethyl [3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl] carbamate; n (3 bromobenzyl) 3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 amine; n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl] 3 (trifluoromethyl)aniline; n [[3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl]methyl] 4 (trifluoromethyl)aniline; pyrazole derivative; unclassified drug; unindexed drug; [3 (4 fluorophenyl) 1 methyl 1h pyrazole 5 yl] methanol; 4-fluoro-N-((3-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-yl)methyl)aniline; aniline derivative; antineoplastic agent; benzamide derivative; prostate specific antigen; pyrazole derivative; antigen expression; antineoplastic activity; apoptosis; Article; comparative study; Curtius rearrangement; down regulation; drug screening; drug synthesis; human; human cell; IC50; in vitro study; LNCaP cell line; male; priority journal; prostate cancer; proton nuclear magnetic resonance; thin layer chromatography; antagonists and inhibitors; chemistry; metabolism; prostate tumor; structure activity relation; synthesis; tumor cell line; Aniline Compounds; Antineoplastic Agents; Benzamides; Cell Line, Tumor; Down-Regulation; Humans; Male; Prostate-Specific Antigen; Prostatic Neoplasms; Pyrazoles; Structure-Activity Relationship