2856-79-3

Usage

Uses

Used in Pharmaceutical Industry:
Benzeneacetic acid, alpha-bromo-2-chloro-, ethyl ester is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex organic compounds that are integral to the development of various medications.
Used in Organic Synthesis:
In the field of organic chemistry, Benzeneacetic acid, .alpha.-broMo-2-chloro-, ethyl ester serves as a key intermediate in the synthesis of other organic compounds, facilitating the creation of a wide range of chemical products through its reactive functional groups.

Upstream product

• 40061-54-9 2-chlorophenylacetic acid ethyl ester 
• 2444-36-2 2'-chloro-benzeneacetic acid 
• 89-98-5 2-chloro-benzaldehyde 
• 1398179-33-3 o-chlorophenyldiazoacetic acid ethyl ester 
• 66985-47-5 2-chloro-α-[(trimethylsilyl)oxy]benzeneacetonitrile 
• 13511-30-3 ethyl 2-(2-chlorophenyl)-2-hydroxyacetate 

Downstream Products

• 77053-65-7 (1R,2S)-1-(2-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 111371-21-2 ethyl (+/-)-2-(2-chlorophenyl)-2-(1H-imidazol-1-yl)acetate 
• 58553-47-2 2-(2-chloro-phenyl)-4H-benzo[1,4]thiazin-3-one 
• 151954-60-8 3-<<4-phenyl>methyl>-5,7-dimethyl-2-ethyl-3H-imidazo<4,5-b>pyridine 
• 141109-25-3 (S)-(+)-2-bromo-2-(2-chlorophenyl)acetic acid 
• 151954-50-6 3-<<4-phenyl>methyl>-5,7-dimethyl-2-ethyl-3H-imidazo<4,5-b>pyridine 

Relevant academic research and scientific papers

Bromination of α-Diazo Phenylacetate Derivatives Using Cobalt(II) Bromide

A method for the bromination of α-diazo phenylacetate derivatives using cobalt(II) bromide is described. This bromination reaction features a short reaction time, broad substrate scope, operational simplicity, acid-free conditions, and gram-scalability. (Figure presented.).

THE METHOD OF MAKING OPTICALLY ACTIVE 2-HALO-2-(N-SUBSTITUTED PHENYL)ACETIC ACID ESTERS AND 2-HALO-2-(N-SUBSTITUTED PHENYL)ACETIC ACIDS BY ENZYMATIC METHOD

The present invention relates to the process for the preparation of optically active 2-halo-2-(n-substituted phenyl)acetic acid esters and optically active 2-halo-2-(n-substituted phenyl)acetic acids, which are used intensively as important chiral intermediates, represented by general formula 2 and 3 respectively from racemic 2-halo-2-(n-substituted phenyl)acetic acid ester represented by general formula 1. In more detail, this invention relates to the process for preparing optically active 2-halo-2-(n-substituted phenyl)acetic acid esters and optically active 2-halo-2-(n-substituted phenyl)acetic acids by stereospecific hydrolysis of racemic 2-halo-2-(n-substituted phenyl)acetic acid esters using hydrolases or hydrolase-producing microorganisms in the aqueous phase or organic phase including aqueous solvent. This method is useful in the practical process because the production and separation of compounds with high optical purity is easier.

ANTIMALARIAL AGENTS HAVING POLYAROMATIC STRUCTURE

Antimalarial agents having a novel pharmacophore of formula (I) are herein described. These polycyclic compounds are able to inhibit chloroquine-sensitive and chloroquine-resistant strains ofPlasmodium falciparum (Pf). Furthermore, the synthesis of these compounds involves few steps from commercial products with low cost of production.Λa présente invention concerne des agents antimalariaux comportant un nouveau pharmacophore de formule (I). Ces composés polycycliques sont susceptibles d''inhiber les souches sensibles à la chloroquine et résistantes à la chloroquine de Plasmodium falciparum (Pf). En outre, la synthèse de ces composés est peu onéreuse et implique peu d''étapes à partir des produits commerciaux.

Design and synthesis of potent antimalarial agents based on clotrimazole scaffold: Exploring an innovative pharmacophore

Identification of new molecular scaffolds structurally unrelated to known antimalarials may represent a valid strategy to overcome resistance of P. falciparum (Pf) to currently available drugs. We describe herein the investigation of a new polycyclic phar

Non-Peptide Angiotensin II Receptor Antagonists. 2. Design, Synthesis, and Biological Activity of N-Substituted (Phenylamino)phenylacetic Acids and Acyl Sulfonamides

The design, synthesis, and biological activity of a new class of highly potent non-peptide AII receptor antagonists derived from N-substituted (phenylamino)phenylacetic acids and acyl sulfonamides which exhibit a high selectivity for the AT1 receptor are described.A series of N-substituted (phenylamino)phenylacetic acids (9) and acyl sulfonamides (16) and a tetrazole derivative (19) were synthesized and evaluated in the in vitro AT1 (rabbit aorta) and AT2 (rat midbrain) binding assay.The (phenylamino)phenylacetic acids 9c (AT1 IC50=4 nM, AT2 IC50=0.74 μM), 9d (AT1 IC50=5.3 nM, AT2 IC50=0.49 μM), and 9e (AT1 IC50=5.3 nM, AT2 IC50=0.56 μM) were found to be the most potent AT1-selective AII antagonists in the acid series.Incorporation of various substituents in the central and bottom phenyl rings led to a decrease in the AT1 and AT2 binding affinity of the resulting compounds.Replacement of the carboxylic acid (CO2H) in 9c, 9d, and 9e with the bioisostere acyl sulfonamide (CONHSO2Ph) resulted in a (5-7)-fold increase in the AT1 potency of 16a (AT1 IC50=0.9 nM, AT2 IC50=0.2 μM), 16b (AT1 IC50=1 nM, AT2 IC50=2.9 μM), and 16c (AT1 IC50=0.8 nM, AT2 IC50=0.42 μM) and yielded acyl sulfonamides with subnanomolar AT1 activity.Incorporation of the acyl sulfonamide (CONHSO2Ph) for the CO2H of 9c not only enhanced the AT1 potency but also effected a marked increase in the AT2 potency of 16a (AT2 IC50=0.74 μM of 9c vs 0.2 μM of 16a) and made it the most potent AT2 antagonist in this study.Replacement of the CO2H of 9b with the bioisostere tetrazole resulted in 19 (AT1 IC50=15 nM) with a 2-fold loss in the AT1 and a complete loss in the AT2 binding affinity. (Phenylamino)phenylacetic acid 9c demonstrated good oral activity in AII-infused conscious normotensive rats at an oral dose of 1.0 mg/kg by inhibiting the pressor response for >6 h.Acyl sulfonamides 16a-c displayed excellent in vivo activity by blocking the AII-induced pressor response for >6 h after oral administration in conscious rats at a 3.0 mg/kg dose level.Both acyl sulfonamides 16a and 16c exhibited superior in vivo activity in rats compared to that of (phenylamino)phenylacetic acid 9c.

1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents

A series of 1-aryl-3-azabicyclohexanes was synthesized by hydride reduction of 1-arylcyclopropanedicarboximides.Hydroxyphenyl analogues 20, 22, and 24 were prepared by EtSNa-DMF ether cleavage of the corresponding methoxyphenyl analogues 2m, 2n, and 23, respectively, with the secondary amines 20 and 22 going through the N-formyl intermediates 19 and 21.The p-ethoxy analogue 26 was obtained by O-ethylation of 19, followed by base hydrolysis of the amide 25.The greatest analgesic potency in mouse writhing and rat paw-pain assays was observed for para-substituted compounds.Bicifadine, 1-(4-methylphenyl)-3-azabicyclohexane (2b), was the most potent member of the series and is presently undergoing clinical trials in man.Analgesic activity of 2b is limited to the (+) enantiomer 2v, which has the 1R,5S absolute configuration as determined by single-crystal X-ray analysis.The N-methyl analogue (27d) of 2b showed significant analgesic potency, whereas the N-allyl (27a), N-(cyclopropylmethyl) (27b), and N-(n-hexyl) (27c) analogues were inactive.Bicifadine (2b) showed a nonnarcotic profile different from analogous azabicycloalkane and 3-phenylpyrrolidine analgesics.