16327-95-0

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

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Novel pyrrolidine ureas as C-C chemokine receptor 1 (CCR1) antagonists

Monocyte infiltration is implicated in a variety of diseases including multiple myeloma, rheumatoid arthritis, and multiple sclerosis. C-C chemokine receptor 1 (CCR1) is a chemokine receptor that upon stimulation, particularly by macrophage inflammatory protein 1a (MIP-1a) and regulated on normal T-cell expressed and secreted (RANTES), mediates monocyte trafficking to sites of inflammation. High throughput screening of our combinatorial collection identified a novel, moderately potent CCR1 antagonist 3. The library hit 3 was optimized to the advanced lead compound 4. Compound 4 inhibited CCR1 mediated chemotaxis of monocytes with an IC50 of 20 nM. In addition, the compound was highly selective over other chemokine receptors. It had good microsomal stability when incubated with rat and human liver microsomes and showed no significant cytochrome P450 (CYP) inhibition. Pharmacokinetic evaluation of the compound in the rat showed good oral bioavailability.

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.

POTENT AND HIGHLY SELECTIVE HETEROAROMATIC INHIBITORS OF NEURONAL NITRIC OXIDE SYNTHASE

Peptidomimetic compounds as can inhibit neuronal nitric oxide synthase (nNOS) for potential treatment in neurodegenerative diseases, such as but not limited to stroke, Alzheimer's disease, Parkinson's disease, Huntington's disease.

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).

Substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-ones and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones as hypoglycemic agents

A series of substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-ones and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones was synthesized from amino alcohols or amino thiols and keto acids. A pharmacological model based on the results obtained with these compounds led to the synthesis and evaluation of a series of isoxazoles and other monocyclic compounds. These were evaluated for their ability to enhance glucose utilization in cultured L6 myocytes. The in vivo hypoglycemic efficacy and potency of these compounds were evaluated in a model of type 2 diabetes mellitus (non-insulin-dependent diabetes mellitus), the ob/ob mouse. 25a(2S) (SDZ PGU 693) was selected for further pharmacological studies.

Photolysis of 3-chloro-3-aryldiazirines in the presence of amines and allyl alcohol

When photolysis of arylchlorodiazirines is performed in the presence of either alkyl- or allyl-substituted amines, either N-alkyl- or N-allyl-substituted amines result as the sole high-yield (64-93%) products. Photolysis in the presence of phenylally-lami

REACTION OF 2-(ARYLIDENEAMINO)ETHANOLS WITH CARBONYL COMPOUNDS

With acetophenone and p-nitroacetophenone in the presence of catalytic amounts of acid 2-(arylideneamino)ethanols form α,β-unsaturated ketones, and with antipyrine they form products from addition at the azomethine bond.