16327-95-0

Basic information

• Product Name: 2-(4-Chlorobenzylideneamino)ethanol
• Synonyms: 2-(4-Chlorobenzylideneamino)ethanol;N-(4-CHLOROBENZYLIDENE)ETHANOLAMINE
• CAS NO: 16327-95-0
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.63
• Mol File: 16327-95-0.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-Chlorobenzylideneamino)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Chlorobenzylideneamino)ethanol(16327-95-0)
• EPA Substance Registry System: 2-(4-Chlorobenzylideneamino)ethanol(16327-95-0)

Safety Data

• Hazardous Substances Data: 16327-95-0(Hazardous Substances Data)

Usage

Molecular weight

320.88 g/mol

Appearance

White crystalline powder

Solubility

Practically insoluble in water, soluble in chloroform and ethanol

Melting point

174-179°C

Antimalarial and anti-inflammatory properties

Inhibits the growth of the malaria parasite in the red blood cells and has immunomodulatory effects

Common uses

Treatment and prevention of malaria, management of autoimmune conditions such as rheumatoid arthritis and lupus erythematosus

Potential efficacy

Treating certain viral infections, including COVID-19

Caution

Use with caution and under the supervision of a healthcare professional due to potential side effects and interactions with other medications.

Upstream product

• 141-43-5 ethanolamine 
• 39184-66-2 (4-chlorophenyl)chlorodiazirine 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 127536-01-0 (2-Allyloxy-ethyl)-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amine 
• 25870-65-9 3-(4-chlorophenyl)-1-(4-nitrophenyl)-2-propen-1-one 
• 40172-04-1 2-(4-chlorobenzylamino)ethanol 
• 1018909-08-4 tert-butyl (2-azidoethyl)(4-chlorobenzyl)carbamate 
• 1018909-30-2 tert-butyl 4-chlorobenzyl(2'-(methylamino)ethyl)carbamate 
• 127536-11-2 (2-Allyloxy-ethyl)-(4-chloro-benzyl)-amine 
• 31867-41-1 2-(4-chloro-phenyl)-oxazolidine-3-carbothioic acid methylamide 
• 21168-88-7 2-(4-chloro-phenyl)-oxazolidine-3-carboxylic acid methylamide 
• 956-04-7 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one 
• 84905-10-2 4-[(4-Chloro-phenyl)-(2-hydroxy-ethylamino)-methyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 21169-30-2 2-(4-chloro-phenyl)-oxazolidine-3-carboxylic acid 3,4-dichloro-anilide 
• 21167-47-5 2-(4-chloro-phenyl)-oxazolidine-3-carboxylic acid anilide 
• 21169-31-3 2-(4-chloro-phenyl)-oxazolidine-3-carbothioic acid ethylamide 

Relevant articles and documents

Discovery of highly potent and selective inhibitors of neuronal nitric oxide synthase by fragment hopping

Selective inhibition of neuronal nitric oxide synthase (nNOS) has been shown to prevent brain injury and is important for the treatment of various neurodegenerative disorders. This study shows that not only greater inhibitory potency and isozyme selectivity but more druglike properties can be achieved by fragment hopping. On the basis of the structure of lead molecule 6, fragment hopping effectively extracted the minimal pharmacophoric elements in the active site of nNOS for ligand hydrophobic and steric interactions and generated appropriate lipophilic fragments for lead optimization. More potent and selective inhibitors with better druglike properties were obtained within the design of 20 derivatives (compounds 7-26). Our structure - based inhibitor design for nNOS and SAR analysis reveal the robustness and efficiency of fragment hopping in lead discovery and structural optimization, which implicates a broad application of this approach to many other therapeutic targets for which known druglike small-molecule modulators are still limited.

PROLINE UREA CCR1 ANTAGONISTS FOR AUTOIMMUNE DISEASES & INFLAMMATION

Compounds of the formulae (I) and (II) are disclosed. The compounds are CCRl antagonists which are useful for the treatment and prevention of inflammatory and autoimmune diseases. Other embodiments are also disclosed.

Structural studies on bioactive compounds. 34.1 Design, synthesis, and biological evaluation of triazenyl-substituted pyrimethamine inhibitors of Pneumocystis carinii dihydrofolate reductase

The triazenyl-pyrimethamine derivative 3a (TAB), a potent and selective inhibitor of Pneumocystis carinii DHFR, was selected as the starting point for a lead optimization study. Molecular modeling studies, corroborated by a recent crystal structure determination of the ternary complex of P. carinii DHFR-NADPH bound to TAB, predicted that modifications to the acetoxy residue of the lead inhibitor could exploit binding opportunities in the vicinity of an active site pocket bounded by residues Ile33, Lys37, and Leu72. Substitutions in the benzyl moiety with electron-donating and electron-withdrawing groups were predicted to probe face-edge interactions with amino acid Phe69 unique to the P. carinii enzyme. New triazenes 10a-v and 12a-f were prepared by coupling the diazonium tetrafluoroborate salt 6b of aminopyrimethamine with substituted benzylamines or phenethylamines. The most potent of the new inhibitors against P. carinii DHFR was the naphthylmethyl-substituted triazene 10t (IC50: 0.053 μM), but a more substantial increase in potency against the rat liver DHFR led to a reduction in selectivity (ratio rat liver DHFR IC50/P. carinii DHFR IC50: 5.36) compared to the original lead structure 3a (ratio rat liver DHFR IC50/P. carinii DHFR IC50: 114).