106841-13-8

Basic information

• Product Name: N-benzyl-4-chloro-2-hydroxybenzamide
• Synonyms: N-benzyl-4-chloro-2-hydroxybenzamide
• CAS NO: 106841-13-8
• Molecular Weight: 261.708
• Mol File: 106841-13-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-benzyl-4-chloro-2-hydroxybenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-4-chloro-2-hydroxybenzamide(106841-13-8)
• EPA Substance Registry System: N-benzyl-4-chloro-2-hydroxybenzamide(106841-13-8)

Safety Data

• Hazardous Substances Data: 106841-13-8(Hazardous Substances Data)

Upstream product

• 5106-98-9 4-chlorosalicylic acid 
• 100-46-9 benzylamine 
• 89-75-8 2,4-dichlorobenzoyl chloride 
• 5397-16-0 N-benzyl-2,4-dichlorobenzamide 
• 50-84-0 2,4 dichlorobenzoic acid 
• 3287-99-8 benzylamine hydrochloride 
• 82944-13-6 4-chloro-2-hydroxybenzoyl chloride 

Relevant articles and documents

Structure-activity relationships of N-benzylsalicylamides for inhibition of photosynthetic electron transport

Inhibition of photosynthetic electron transport (PET) in spinach chloroplasts by sixty-one ring-substituted N-benzylsalicylamides was investigated. The inhibitory potency of the compounds expressed by IC50 value varied from 2.0 to 425.3 μmol/L. Several evaluated compounds can be considered as effective PET inhibitors; these include N-(3,4- dichlorobenzyl)-2-hydroxy-5-nitrobenzamide (IC50 = 2.0 μmol/L), 3,5-dibromo-N-(3,4-dichlorobenzyl)-2-hydroxybenzamide (IC50 = 2.3 μmol/L) and 3,5-dibromo-N-(4-chlorobenzyl)-2-hydroxybenzamide (IC50 = 2.6 μmol/L) with activity comparable with that of the standard Diuron (IC50 = 1.9 μmol/L). The PET inhibiting activity increased approximately linearly with increasing lipophilicity of the compounds as well as with the increasing sum of Hammett σ constants of the substituents on the acyl fragment (R1 = H, 5-OCH3, 5-CH3, 5-Cl, 5-Br, 5-NO2, 4-OCH3, 4-Cl, 3,5-Cl and 3,5-Br) and the benzylamide fragment (R2 = H, 4-OCH3, 4-CH3, 4-F, 4-Cl and 3,4-Cl). Based on the evaluated structure-PET inhibiting activity relationships (QSAR) it was confirmed that the inhibitory activity of the compounds depends on lipophilicity (log P or distributive parameters π1 and π2 of individual substituents) and electronic properties of the substituents on the acyl (σ1) and the benzylamide fragments (σ2), the contribution of σ1 being more significant than that of σ2.

Design and synthesis of highly potent and selective (2-arylcarbamoyl- phenoxy)-acetic acid inhibitors of aldose reductase for treatment of chronic diabetic complications

Recent efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective (2-arylcarbamoyl-phenoxy)-acetic acid aldose reductase inhibitors. The compound class features a core template that utilizes an intramolecular hydrogen bond to position the key structural elements of the pharmacophore in a conformation, which promotes a high binding affinity. The lead candidate, example 40, 5-fluoro-2-(4-bromo-2-fluoro-benzylthiocarbamoyl)-phenoxyacetic acid, inhibits aldose reductase with an IC50 of 30 nM, while being 1100 times less active against aldehyde reductase, a related enzyme involved in the detoxification of reactive aldehydes. In addition, example 40 lowers nerve sorbitol levels with an ED50 of 31 mg/kg/d po in the 4-day STZ-induced diabetic rat model.