5818-63-3

Basic information

• Product Name: 3-[1-(4-bromophenyl)-1H-pyrrol-2-yl]-2-cyano-N-phenylprop-2-enamide
• CAS NO: 5818-63-3
• Molecular Formula: C₂₀H₁₄BrN₃O
• Molecular Weight: 392.2487
• Mol File: 5818-63-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 601.9°C at 760 mmHg
• Flash Point: 317.8°C
• Density: 1.34g/cm³
• Vapor Pressure: 1.92E-14mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: 3-[1-(4-bromophenyl)-1H-pyrrol-2-yl]-2-cyano-N-phenylprop-2-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[1-(4-bromophenyl)-1H-pyrrol-2-yl]-2-cyano-N-phenylprop-2-enamide(5818-63-3)
• EPA Substance Registry System: 3-[1-(4-bromophenyl)-1H-pyrrol-2-yl]-2-cyano-N-phenylprop-2-enamide(5818-63-3)

Safety Data

• Hazardous Substances Data: 5818-63-3(Hazardous Substances Data)

Upstream product

• 108-31-6 maleic anhydride 
• 496-15-1 1-indoline 

Relevant articles and documents

Rational Design of an Indolebutanoic Acid Derivative as a Novel Aldose Reductase Inhibitor Based on Docking and 3D QSAR Studies of Phenethylamine Derivatives

A series of 45 phenethylamine derivatives were synthesized and evaluated for their inhibitory activity against pig kidney aldose reductase (ALR2, EC 1.1.1.21). Their IC50 values ranged from 400 μM to 24 μM. The binding modes of compounds at the active site of ALR2 were examined using flexible docking. The results indicated that phenethylamine derivatives nicely fit into the active pocket of ALR2 by forming various hydrogen bonding and hydrophobic interactions. 3D-QSAR analysis was also conducted using FlexX-docked alignment of the compounds. The best prediction was obtained by CoMSIA combined with hydrophobic and hydrogen bond donor/acceptor field (q 2 = 0.557, r2 = 0.934). A new derivative, 4-oxo-4-(4-hydroxyindole)butanoic acid, was designed, taking into account the CoMSIA field and the binding mode derived by FlexX docking. This rationally designed compound exhibits an ALR2 inhibition with an IC50 value of 7.4 μM, which compares favorably to that of a well-known ALR2 inhibitor, tolrestat (IC50 = 16 μM) and represents a potency approximately 240-fold higher than that of an original phenethylamine lead compound, YUA001.