1297540-77-2

Basic information

• Product Name: (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile
• Synonyms: (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile
• CAS NO: 1297540-77-2
• Molecular Weight: 278.716
• Mol File: 1297540-77-2.mol

Chemical Properties

• CAS DataBase Reference: (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile(1297540-77-2)
• EPA Substance Registry System: (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile(1297540-77-2)

Safety Data

• Hazardous Substances Data: 1297540-77-2(Hazardous Substances Data)

Upstream product

• 1297540-76-1 2-Chloro-6-fluoro-4-(1H-pyrazol-5-yl)benzonitrile 
• 79069-13-9 (S)-2-t-butoxycarbonylaminopropan-1-ol 
• 1297540-76-1 2-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrile 
• 96042-30-7 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 147252-84-4 tert-butyl (1-hydroxypropan-2-yl)carbamate 
• 1297540-69-2 4-bromo-3-chloro-5-fluoroaniline 
• 1095188-13-8 4-amino-2-chloro-6-fluorobenzonitrile 
• 1297540-72-7 2-Chloro-6-fluoro-4-iodobenzonitrile 
• 1297540-73-8 2-Chloro-6-fluoro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile 
• 4863-91-6 3-chloro-5-fluoroaniline 

Downstream Products

• 1403332-70-6 (S)-5-(Bromomethyl)-N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)isoxazole-3-carboxamide 
• 1403332-68-2 (S)-5-((1H-Imidazol-1-yl)methyl)-N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)isoxazole-3-carboxamide 
• 1403333-92-5 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-cyclopropyl-1H-pyrazole-3-carboxamide 
• 1403332-54-6 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxamide 
• 1403332-61-5 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-isopropyl-1,2,4-oxadiazole-5-carboxamide 
• 1403332-49-9 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-6-cyanoimidazo[1,2-a]pyridine-2-carboxamide 
• 1403332-72-8 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-oxo-5,6-dihydroimidazo[1,2-c]pyrimidine-2-carboxamide 
• 1403333-23-2 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3,3'-bipyridine-6-carboxamide 
• 1403333-28-7 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-6-(3,3-dimethylureido)imidazo[1,2-a]pyridine-2-carboxamide 
• 1403333-34-5 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-6-(methylsulfonamido)imidazo[1,2-a]pyridine-2-carboxamide 
• 1403333-40-3 N-((S)-1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1-hydroxy-2-methylpropyl)isoxazole-3-carboxamide 
• 1403333-47-0 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1,5-dimethyl-1H-pyrazol-3-yl)-1,2,4-oxadiazole-3-carboxamide 
• 1403333-54-9 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(isoxazol-3-yl)-1,2,4-oxadiazole-3-carboxamide 
• 1403333-66-3 (S)-N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-(1-trityl-1H-imidazol-4-yl)-1H-pyrazole-5-carboxamide 

Relevant articles and documents

Discovery and biological evaluation of darolutamide derivatives as inhibitors and down-regulators of wild-type AR and the mutants

Androgen receptor (AR) has been a target of prostate cancer (PC) for nearly six decades. Recently, downregulating or degrading AR and the mutants especially the splice variant 7 (AR-V7) lacking ligand binding domain (LBD) emerged as an advantageous therapeutic approach to overcome drug resistance. Here, the structural modification of darolutamide resulted in the discovery of dual-action AR inhibitors and down-regulators. Unlike other traditional AR antagonists targeting the AR-LBD, compounds 4k and 4b not only inhibit the activities of wt-AR and AR-F876L mutant but also downregulate the protein expression of full-length (AR-full) and AR variant 7 (AR-V7) at mRNA level. In cell proliferation assays, compounds 4k and 4b exhibited better antiproliferative activities than darolutamide and enzalutamide against AR-V7-positive 22Rv1 cells and VCaP cells. In addition, 4k demonstrated better antitumor activity than clinically used enzalutamide in castration-resistant VCaP xenograft model. Collectively, combining the activities of AR inhibition and downregulation, compound 4k is proposed as an advantageous lead compound to disrupt AR signaling and overcome resistance.

ANDROGEN RECEPTOR MODULATING CARBOXAMIDES

Compounds of formula (I) or (II) wherein Rx, Rz, R9, R10, R14, R14′, R15, R15′, A and B are as defined in the claims and pharmaceutically acceptable salts and esters thereof, are disclosed. The compounds possess utility as tissue-selective androgen receptor modulators (SARM) and are useful as medicaments in the treatment of prostate cancer and other AR dependent conditions and diseases where AR antagonism is desired.

ANDROGEN RECEPTOR MODULATING CARBOXAMIDES

Compounds of formula (I) wherein Rx, Rz, R9, R10, R14, R14', R15, R15', A and B are as defined in the claims and pharmaceutically acceptable salts and esters thereof, are disclosed. The compounds possess utility as tissue-selective androgen receptor modulators (SARM) and are particularly useful as medicaments in the treatment of prostate cancer and other AR dependent conditions and diseases where AR antagonism is desired.

ANDROGEN RECEPTOR MODULATING COMPOUNDS

Compounds of formula (I) wherein R1 to R16, A. B and E are as defined in the claims and pharmaceutically acceptable salts and esters thereof, are disclosed. The compounds of formula (I) possess utility as tissue-selective androgen receptor modulators (SARM) and are particularly useful as medicaments in the treatment of prostate cancer and other AR dependent conditions and diseases where AR antagonism is desired.