58622-66-5

Basic information

• Product Name: 4-chloro-N-(3,4-dichlorophenyl)-2-hydroxybenzamide
• Synonyms: 4-chloro-N-(3,4-dichlorophenyl)-2-hydroxybenzamide
• CAS NO: 58622-66-5
• Molecular Weight: 316.571
• Mol File: 58622-66-5.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 4-chloro-N-(3,4-dichlorophenyl)-2-hydroxybenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-N-(3,4-dichlorophenyl)-2-hydroxybenzamide(58622-66-5)
• EPA Substance Registry System: 4-chloro-N-(3,4-dichlorophenyl)-2-hydroxybenzamide(58622-66-5)

Safety Data

• Hazardous Substances Data: 58622-66-5(Hazardous Substances Data)

Upstream product

• 5106-98-9 4-chlorosalicylic acid 
• 95-76-1 m,p-dichloroaniline 

Downstream Products

• 1552270-41-3 O-{5-chloro-2-[(3,4-dichlorophenyl)carbamoyl]phenyl}O,O-diethyl phosphate 
• 1227476-93-8 BrH*C₂₂H₁₇Cl₃N₂O₃ 
• 1227476-92-7 BrH*C₁₈H₁₇Cl₃N₂O₃ 
• 1227477-33-9 4-chloro-N-{(2S)-1-[(3,4-dichlorophenyl)amino]-1-oxo-3-phenylpropan-2-yl}-2-hydroxybenzamide 
• 1227477-32-8 4-chloro-N-{(2S)-1-[(3,4-dichlorophenyl)amino]-3-methyl-1-oxobutan-2-yl}-2-hydroxybenzamide 
• 1422904-48-0 C₂₀H₁₂Cl₃NO₃ 
• 1403607-24-8 5-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl 4-(trifluoromethyl)benzoate 
• 1426258-44-7 4-chloro-1-[(3,4-dichlorophenyl)carbamoyl]phenyl pyrazine-2-carboxylate 
• 1261296-11-0 (S)-5-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoate 

Relevant articles and documents

2-Hydroxy-N-Phenylbenzamides and their esters inhibit acetylcholinesterase and Butyrylcholinesterase

The development of novel inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) represents a viable approach to alleviate Alzheimer’s disease. Thirty-six halogenated 2-hydroxy-N-phenylbenzamides (salicylanilides) with various substitution patterns and their esters with phosphorus-based acids were synthesized in yields of 72% to 92% and characterized. They were evaluated for in vitro inhibition of AChE from electric eel and BuChE from equine serum using modified Ellman’s spectrophotometric method. The benzamides exhibited a moderate inhibition of AChE with IC50 values in a narrow concentration range from 33.1 to 85.8 μM. IC50 values for BuChE were higher (53.5–228.4 μM). The majority of derivatives inhibit AChE more efficiently than BuChE and are comparable or superior to rivastigmine—an established cholinesterases inhibitor used in the treatment of Alzheimer’s disease. Phosphorus-based esters especially improved the activity against BuChE with 5-chloro-2-{[4-(trifluoromethyl)phenyl]carbamoyl}phenyl diethyl phosphite 5c superiority (IC50 = 2.4 μM). This derivative was also the most selective inhibitor of BuChE. It caused a mixed inhibition of both cholinesterases and acted as a pseudo-irreversible inhibitor. Several structure-activity relationships were identified, e.g., favouring esters and benzamides obtained from 5-halogenosalicylic acids and polyhalogenated anilines. Both 2-hydroxy-N-phenylbenzamides and esters share convenient physicochemical properties for blood-brain-barrier penetration and thus central nervous system delivery.

Novel salicylanilides from 4,5-dihalogenated salicylic acids: Synthesis, antimicrobial activity and cytotoxicity

Salicylanilides have proved their activity against tuberculosis (TB). One weak electron-withdrawing substituent is favored at the salicylic part, specially Cl or Br atoms at positions 4 or 5. On the other hand, the antimycobacterial activity of salicylanilides is negatively affected when a strong electron-withdrawing substituent ([sbnd]NO2) is present at the same positions. Herein we describe the synthesis and characterization of novel salicylanilides possessing two weak electron-withdrawing groups (halogen atoms) at their salicylic part and compare their antitubercular activity with their monohalogenated analogues. All dihalogenated derivatives proved to possess antitubercular activity at a very narrow micromolar range (MIC?=?1–4?μM), similar with their most active monohalogenated analogues. More importantly, the most active final molecules were further screened against multidrug resistant strains and found to inhibit their growth at the range of 0.5–4?μM.

Salicylanilide diethyl phosphates: Synthesis, antimicrobial activity and cytotoxicity

A series of 27 salicylanilide diethyl phosphates was prepared as a part of our on-going search for new antimicrobial active drugs. All compounds exhibited in vitro activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium strains, with minimum inhibitory concentration (MIC) values of 0.5-62.5 μmol/L. Selected salicylanilide diethyl phosphates also inhibit multidrug-resistant tuberculous strains at the concentration of 1 μmol/L. Salicylanilide diethyl phosphates also exhibited mostly the activity against Gram-positive bacteria (MICs ≥1.95 μmol/L), whereas their antifungal activity is significantly lower. The IC50 values for Hep G2 cells were within the range of 1.56-33.82 μmol/L, but there is no direct correlation with MICs for mycobacteria.