166809-85-4

Basic information

• Product Name: 4-(4-nitrophenyl)-3-(2-cyanoethoxy)carbonyl-3-buten-2-one
• Synonyms: 4-(4-nitrophenyl)-3-(2-cyanoethoxy)carbonyl-3-buten-2-one
• CAS NO: 166809-85-4
• Molecular Weight: 288.26
• Mol File: 166809-85-4.mol

Chemical Properties

• CAS DataBase Reference: 4-(4-nitrophenyl)-3-(2-cyanoethoxy)carbonyl-3-buten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-nitrophenyl)-3-(2-cyanoethoxy)carbonyl-3-buten-2-one(166809-85-4)
• EPA Substance Registry System: 4-(4-nitrophenyl)-3-(2-cyanoethoxy)carbonyl-3-buten-2-one(166809-85-4)

Safety Data

• Hazardous Substances Data: 166809-85-4(Hazardous Substances Data)

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 65193-87-5 2-cyanoethylacetoacetate 
• 110-89-4 piperidine 

Downstream Products

• 166809-88-7 3-(2-cyanoethoxycarbonyl)-5-(benzyloxycarbonyl)-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine 
• 251930-31-1 4-(4-nitrophenyl)-6-methyl-2-methoxy-3,4-dihydropyrimidine-5-carboxylic acid cyanoethyl ester 
• 166808-36-2 5-[3-(4-methoxycarbonyl-4-phenyl-piperidin-1-yl)-propylcarbamoyl]-2,6-dimethyl-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2-cyano-ethyl ester 
• 166808-37-3 5-[3-(4-methoxycarbonyl-4-phenyl-piperidin-1-yl)-propylcarbamoyl]-2,6-dimethyl-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 
• 166809-89-8 3-(2-cyanoethoxycarbonyl)-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine-5-carboxylic acid 
• 251930-34-4 5-(cyanoethoxycarbonyl)-1-{N-[3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)propyl]carboxamido}-4-methyl-6-(4-nitrophenyl)-2-oxo-1,2,3,6-tetrahydropyrimidine 
• 251930-36-6 3-[3-(4-methoxycarbonyl-4-phenyl-piperidin-1-yl)-propylcarbamoyl]-6-methyl-4-(4-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid 
• 251930-33-3 5-(2-cyanoethoxycarbonyl)-1,6-dihydro-2-methoxy-4-methyl-6-(4-nitrophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine 
• 251930-31-1 2-methoxy-6-methyl-4-(4-nitro-phenyl)-1,4-dihydro-pyrimidine-5-carboxylic acid 2-cyano-ethyl ester 

Relevant articles and documents

Design and synthesis of novel α1a adrenoceptor-selective dihydropyridine antagonists for the treatment of benign prostatic hyperplasia

We report the synthesis and evaluation of novel ttia adrenoceptor subtype-selective antagonists. Systematic modification of the lipophilic 4,4-diphenylpiperidinyl moiety of the dihydropyridine derivatives 1 and 2 provided several highly selective and potent α1a antagonists. From this series, we identified the 4-(methoxycarbonyl)-4-phenylpiperidine analogue SNAP 5540 (-) [(-)-63] for further characterization. When examined in an isolated human prostate tissue assay, this compound was found to have a Ki of 2.8 nM, in agreement with the cloned human receptor binding data (Ki = 2.42 nM). Further evaluation of the compound in isolated dog prostate tissue showed a Ki of 3.6 nM and confirmed it to be a potent antagonist (Kb = 1.6 nM). In vivo, this compound effectively blocked the phenylephrine-stimulated increase in intraurethral pressure (IUP) in mongrel dogs, at doses which did not significantly affect the arterial pressure (diastolic blood pressure, DBF), with a DBF Kb/IUP-Kb ratio of 16. In addition, (-)-63 also showed greater than 40 000-fold selectivity over the rat L-type calcium channel and 200-fold selectivity over several G protein-coupled receptors, including histamine and serotonin subtypes. These findings prove that aia adrenoceptor-subtype selective antagonists such as (-)-63 may be developed as uroselective agents for an improved treatment of BPH over nonselective 0.1 antagonists such as prazosin and terazosin, with fewer side effects.