134346-48-8

Basic information

• Product Name: 7-{4-[4-(cyclohexylmethyl)piperazin-1-yl]-4-oxobutoxy}-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one
• Synonyms: 1-[4-(cyclohexylmethyl)piperazin-1-yl]-4-[(2-hydroxy-4H-imidazo[4,5-b]quinolin-7-yl)oxy]butan-1-one; 1-butanone, 1-[4-(cyclohexylmethyl)-1-piperazinyl]-4-[(2-hydroxy-4H-imidazo[4,5-b]quinolin-7-yl)oxy]-
• CAS NO: 134346-48-8
• Molecular Formula: C₂₅H₃₃N₅O₃
• Molecular Weight: 451.5612
• Mol File: 134346-48-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 607.5°C at 760 mmHg
• Flash Point: 321.2°C
• Density: 1.232g/cm³
• Vapor Pressure: 1.06E-14mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: 7-{4-[4-(cyclohexylmethyl)piperazin-1-yl]-4-oxobutoxy}-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-{4-[4-(cyclohexylmethyl)piperazin-1-yl]-4-oxobutoxy}-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one(134346-48-8)
• EPA Substance Registry System: 7-{4-[4-(cyclohexylmethyl)piperazin-1-yl]-4-oxobutoxy}-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one(134346-48-8)

Safety Data

• Hazardous Substances Data: 134346-48-8(Hazardous Substances Data)

Upstream product

• 2550-36-9 Cyclohexylmethyl bromide 
• 412293-89-1 4-Cyclohexylmethyl-piperazine-1-carbaldehyde 
• 57184-23-3 1-cyclohexylmethylpiperazine 
• 130288-93-6 4-[(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)oxy]butanoic acid 

Relevant articles and documents

Inhibitors of Blood Platelet cAMP Phosphodiesterase. 3. 1,3-Dihydro-2H-imidazoquinolin-2-one Derivatives with Enhanced Aqueous Solubility

Two series of 1,3-dihydro-2H-imidazoquinolin-2-one derivatives incorporating an additional site for acid salt formation were synthesized and evaluated as inhibitors of human blood platelet cAMP phosphodiesterase (PDE) and ADP-induced platelet aggregation.The objective of this study was to identify compounds that blended potent biological activity with a satisfactory level of aqueous solubility.From a series of 7-aminoimidazoquinolin-2-ones, biological and physical properties were optimally combined in the 1-piperidinyl derivative 11c.However, this compound offered no significant advantage over earlier studied compounds as an antithrombotic agent in an animal model of small vessel thrombosis.A series of 7-alkoxy alkanoic piperazinamide derivatives, in which the additional basic nitrogen atom was remote from the heterocyclic nucleus and accomodated in a secondary binding region of the cAMP PDE enzyme, demonstrated greater intrinsic cAMP PDE inhibitory activity.Structural modifications of this series focused on variation of the piperazine substituent and side-chain length.The lipophilicity of the N-substituent influenced biological potency and aqueous solubility, with substituents of seven carbon atoms or less generally providing acceptable solubility properties.The N-(cyclohexylmethyl)piperazinamide 21h was identified from this series of compounds as a potent inhibitor of platelet cAMP PDE, IC50 = 0.4 nM and ADP-induced platelet aggregation, IC50 = 0.51 μM after a 3-min exposure and 0.1 μM after a 15-min exposure of platelet-rich plasma to the drug.Evaluation of 21h and representative analogues in vivo using a rabbit model of small vessel thrombosis revealed significantly greater antithrombotic efficacy compared to that of previously studied compounds with similar intrinsic biological activity measured in vitro but inferior aqueous solubility.