105911-55-5

Basic information

• Product Name: 6-(3-chlorophenyl)hexanoic acid
• Synonyms: 6-(3-chlorophenyl)hexanoic acid
• CAS NO: 105911-55-5
• Molecular Formula: C₁₂H₁₅ClO₂
• Molecular Weight: 226.6993
• EINECS: -0
• Mol File: 105911-55-5.mol

Chemical Properties

• Boiling Point: 372.6±25.0 °C(Predicted)
• Appearance: /
• Density: 1.163±0.06 g/cm3(Predicted)
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: 6-(3-chlorophenyl)hexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(3-chlorophenyl)hexanoic acid(105911-55-5)
• EPA Substance Registry System: 6-(3-chlorophenyl)hexanoic acid(105911-55-5)

Safety Data

• Hazardous Substances Data: 105911-55-5(Hazardous Substances Data)

Upstream product

• 1034980-73-8 (5E,Z)-6-(3-chlorophenyl)hex-5-enoic acid 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 

Relevant articles and documents

Identification of highly potent N-acylethanolamine acid amidase (NAAA) inhibitors: Optimization of the terminal phenyl moiety of oxazolidone derivatives

N-acylethanolamine acid amidase (NAAA) is a cysteine hydrolase that participates in the deactivation of fatty acid ethanolamides, such as palmitoylethanolamide (PEA). NAAA inhibition may provide a potential therapeutic strategy for the treatment of diseases in which higher PEA level is desired. In the present study, we reported the structure-activity relationship (SAR) studies for oxazolidone derivatives as NAAA inhibitors. A series of substituents or alkyl replacements for the terminal phenyl ring of oxazolidone derivatives were examined. The results showed that the inhibition potency of these oxazolidone derivatives towards NAAA depends on the sizes, flexibility, and lipophilicity of the terminal groups. SAR results suggested that small lipophilic 3-phenyl substituents or hydroxy-containing 4-phenyl substituents were preferable for optimal potency. Furthermore, the distal aliphatic replacement is also preferred for high inhibitory potency. Rapid dilution and kinetic analysis suggested that oxazolidone derivatives with different terminal phenyl moieties inhibited NAAA via different mechanisms. This study identified several highly potent NAAA inhibitors, including 1a (F215, IC50 = 0.009 μM), 1o (IC50 = 0.061 μM) and 2e (IC50 = 0.092 μM), and also determined structural requirements of oxazolidone derivatives for potent inhibition against NAAA.

Conformationally constrained analogues of N-(piperidinyl)-5-(4- chlorophenyl)-1-(2,4- dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716): Design, synthesis, computational analysis, and biological evaluations

Structure-activity relationships (SARs) of 1 (SR141716) have been extensively documented, however, the conformational properties of this class have received less attention. In an attempt to better understand ligand conformations optimal for receptor recognition, we have designed and synthesized a number of derivatives of 1, including a four-carbon-bridged molecule (11), to constrain rotation of the diaryl rings. Computational analysis of 11 indicates a ～20 kcal/mol energy barrier for rotation of the two aryl rings. NMR studies have determined the energy barrier to be ～18 kcal/mol and suggested atropisomers could exist. Receptor binding and functional studies with these compounds displayed reduced affinity and potency when compared to 1. This indicates that our structural modifications either constrain the ring systems in a suboptimal orientation for receptor interaction or the introduction of steric bulk leads to disfavored steric interactions with the receptor, and/or the relatively modest alterations in the molecular electrostatic potentials results in disfavored Coulombic interactions.