64834-58-8

Usage

Structure

A derivative of ethanol with a chlorine and benzyl group attached to the amino group

Potential applications

Pharmaceutical industry as a building block in the synthesis of various pharmaceutical compounds, and is being investigated for its potential therapeutic effects

Uses

Chemical research and development

Safety measures

Should be handled with caution and proper safety measures should be followed when working with 2-(2-CHLORO-BENZYLAMINO)-ETHANOL.

InChI:InChI=1/C9H12ClNO/c10-9-4-2-1-3-8(9)7-11-5-6-12/h1-4,11-12H,5-7H2

Upstream product

• 71006-02-5 2-(2-chloro-benzylideneamino)-ethanol 
• 89-98-5 2-chloro-benzaldehyde 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 141-43-5 ethanolamine 

Downstream Products

• 1123813-00-2 (R)-N₂-(2-chlorobenzyl)-N₁-(4-chlorophenyl)-N₂-(2-hydroxyethyl)pyrrolidine-1,2-dicarboxamide 
• 82771-60-6 7-chloro-1,2,3,4-tetrahydro-isoquinoline 
• 75416-50-1 8-chloro-1,2,3,4-tetrahydroisoquinoline 
• 61563-33-5 8-chloro-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 17683-37-3 2-[(2-chloro-benzyl)-methyl-amino]-ethanol 
• 102312-81-2 3-{2-[(2-chloro-benzyl)-methyl-amino]-ethoxy}-propionitrile 
• 106214-08-8 [2-(3-amino-propoxy)-ethyl]-(2-chloro-benzyl)-methyl-amine 

Relevant academic research and scientific papers

Synthesis and further transformations of 8-chloro-3,4-dihydroisoquinoline

Two procedures for the synthesis of barely accessible 8-chloro-3,4-dihydroisoquinoline were investigated. The first approach is based on a directed ortho-lithiation of N-pivaloyl meta-chlorophenylethylamine, followed by formylation and subsequent ring closure under acidic conditions. In the second, more advantageous variant, the N-hydroxyethyl ortho-chlorobenzylamine intermediate undergoes a Friedel-Crafts reaction, and the resulting tetrahydro derivative is oxidized with N-bromosuccinimide. The 8-chloro-3,4-dihydroisoquinoline key intermediate is then applied in Suzuki reactions to give various 8-aryl-3,4-dihydroisoquinolines, which are finally treated with alkyl or aryllithiums to give 1-substituted 8-aryl-1,2,3,4-tetrahydroisoquinolines. These novel 1,2,3,4-tetrahydroisoquinoline derivatives can be used as building blocks in the synthesis of potential drug candidates.

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.

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).