90096-18-7

Basic information

• Product Name: Butanoic acid, 3-oxo-, 2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl ester
• CAS NO: 90096-18-7
• Molecular Formula: C16H21FN2O3
• Molecular Weight: 308.34800
• Mol File: 90096-18-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 3-oxo-, 2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 3-oxo-, 2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl ester(90096-18-7)
• EPA Substance Registry System: Butanoic acid, 3-oxo-, 2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl ester(90096-18-7)

Safety Data

• Hazardous Substances Data: 90096-18-7(Hazardous Substances Data)

Upstream product

• 2252-63-3 1-(4-Fluorophenyl)piperazine 
• 674-82-8 4-methyleneoxetan-2-one 
• 90096-38-1 2-<4-(4-fluorophenyl)piperazin-1-yl>ethanol 

Downstream Products

• 90095-93-5 2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 90119-99-6 2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl methyl 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 90095-92-4 ethyl 2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 89226-76-6 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethyl} ester 5-methyl ester 

Relevant articles and documents

Syntheses, calcium channel antagonist and anticonvulsant activities of substituted 1,4-dihydro-3,5-pyridinedicarboxylates containing various 3-alkyl ester substituents

A group of 3-alkyl-5-isopropyl 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates 10-20 containing an amine, quaternary ammonium, aryl(heteroaryl)alkenyl, 4-(4-fluorophenyl)-piperazin-1-yl or methoxy moiety in the C-3 alkyl ester R-substituent in combination with a C-4 phenyl ring bearing a 2,3-Cl2, 3-NO2, 3-NMe2, 4-NMe2 or 3,4,5-(OMe)3 X-substituent were prepared using the Hantzsch 1,4-dihydropyridine reaction. In vitro calcium channel antagonist activity (CCA) was determined using a guinea pig ileum longitudinal smooth muscle assay. In the C-4 3-nitrophenyl series of compounds, the C-3 ester R substituent was a determinant CCA activity where the relative potency order was -CH2CH2CH=C-(2-methylphenyl)2 ≤ -CH2CH2NMe2.HCl > -CH2CH2CH=C (3-methyl-2-thienyl)2 > -CH2CH2+NMe3I-. The position and nature of the C-4 phenyl X-substituent, were also determinants of CCA activity where the relative activity order was 3-NMe2>4-NMe2>3,4,5-(OMe)3. Anticonvulsant activities were determined in mice using the subcutaneous metrazol (scMet) and maximal electroshock (MES) screens. The compounds investigated were generally not effective for protecting against scMet induced seizures, except for 10 {X = 2,3-Cl2, R = 2-[4-(4-fluorophenyl)piperazin-1-yl]ethyl} and 14a (X = 3-NMe2.HCl, R = CH2CH2OMe), which exhibited modest activity. Compound 11a (X = 3-NO2, R = -CH2CH2NMe2.HCl) was the most effective agent in the MES screen. All of the compounds investigated, except for 11b (X = 3-NO2, R = -CH2CH2+NMe3 I-, Kp = 0.15) are lipophilic with n-octanol/aqueous phosphate buffer (pH = 7.4) partition coefficients (Kp) in the 121-424 range relative to the reference drug nimodipine (Kp = 187). The structure-activity relationship acquired reinforce the concept that calcium is only one of several factors that are involved in seizure generation.

New 1,4-dihydropyridine derivatives with potent and long-lasting hypotensive effect

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