16555-60-5

Usage

Uses

Used in Pharmaceutical Industry:
(2-CHLORO-BENZOYLAMINO)-ACETIC ACID is used as an active pharmaceutical ingredient for the development of medications targeting neurological disorders and cardiovascular conditions. Its anticonvulsant properties make it a candidate for the treatment of epilepsy and other seizure-related conditions, while its cardiotonic activity suggests potential benefits in strengthening heart muscle contractions and improving cardiac function.
Used in Metabolic Research:
In the field of metabolic research, (2-CHLORO-BENZOYLAMINO)-ACETIC ACID serves as a valuable compound for studying the metabolic pathways of Isoprophenamine and Ticlopidine. Understanding its role as a metabolite can provide insights into drug metabolism, pharmacokinetics, and potential drug interactions, which are crucial for the development of safe and effective medications.
Used in Chemical Synthesis:
(2-CHLORO-BENZOYLAMINO)-ACETIC ACID can also be utilized as a key intermediate in the synthesis of various chemical compounds and pharmaceuticals. Its unique structure allows for further chemical modifications and the creation of new molecules with potential therapeutic applications.
Overall, (2-CHLORO-BENZOYLAMINO)-ACETIC ACID is a versatile compound with applications in the pharmaceutical industry, metabolic research, and chemical synthesis, highlighting its importance in the development of new treatments and understanding of biological processes.

InChI:InChI=1/C9H8ClNO3/c10-7-4-2-1-3-6(7)9(14)11-5-8(12)13/h1-4H,5H2,(H,11,14)(H,12,13)/p-1

Upstream product

• 1242052-34-1 C₁₃H₁₆ClNO₃ 
• 90562-52-0 2-chloro-N-(2-hydroxyethyl)benzamide 
• 609-65-4 o-chlorobenzoyl chloride 
• 66824-94-0 (2-Chloro-benzoylamino)-acetic acid ethyl ester 
• 125700-02-9 (2-chloro-benzoylamino)-acetic acid methyl ester 
• 118-91-2 ortho-chlorobenzoic acid 
• 56-40-6 glycine 

Downstream Products

• 4211-98-7 2-(2-chloro-phenyl)-4-thiophen-2-ylmethylene-4H-oxazol-5-one 
• 22269-63-2 2-(2-chloro-phenyl)-4-(4-dimethylamino-2-methyl-benzylidene)-4H-oxazol-5-one 
• 40547-08-8 2-(2-chloro-phenyl)-4-(3-nitro-benzylidene)-4H-oxazol-5-one 
• 40547-06-6 4-benzylidene-2-(2-chloro-phenyl)-4H-oxazol-5-one 
• 60776-70-7 2-(2-chloro-phenyl)-oxazole-4,5-dione 4-p-tolylhydrazone 
• 22635-16-1 2-(2-chloro-phenyl)-4-isopropylidene-4H-oxazol-5-one 
• 19500-44-8 3,3'-{4-[2-(2-chloro-phenyl)-5-oxo-oxazol-4-ylidenemethyl]-phenylazanediyl}-bis-propionitrile 
• 20063-42-7 3,3'-{4-[2-(2-chloro-phenyl)-5-oxo-oxazol-4-ylidenemethyl]-3-methyl-phenylazanediyl}-bis-propionitrile 
• 39052-65-8 4-[4-(benzyl-methyl-amino)-benzylidene]-2-(2-chloro-phenyl)-4H-oxazol-5-one 
• 159043-72-8 (+)-menthyl 2'-chloro-hippurate 
• 159043-71-7 (-)-menthyl 2'-chloro-hippurate 
• 173345-06-7 4-dimethylaminomethylene-2-(2-chlorophenyl)oxazol-5(4H)-one 
• 56-40-6 glycine 
• 118-91-2 ortho-chlorobenzoic acid 

Relevant academic research and scientific papers

Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents

As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value of 4Bs was above 526, indicating the favorable safety profile. Interestingly, unlike nucleoside analogue 3TC, 4Bs could significantly inhibit 3.5 kb pgRNA expression. Molecular docking study revealed that 4Bs could fit well into the dimer-dimer interface of HBV core protein by hydrophobic, π–π and H-bond interactions. Considering the potent anti-HBV activity, low toxicity and diverse anti-HBV mechanism from that of nucleoside anti-HBV agent 3TC, compound 4Bs might be a promising lead to develop novel non-nucleoside anti-HBV therapeutic agents, and warranted further investigation.

4-Sulfamoylphenylalkylamides as Inhibitors of Carbonic Anhydrases Expressed in Vibrio cholerae

A current issue of antimicrobial therapy is the resistance to treatment with worldwide consequences. Thus, the identification of innovative targets is an intriguing challenge in the drug and development process aimed at newer antimicrobial agents. The state-of-art of anticholera therapy might comprise the reduction of the expression of cholera toxin, which could be reached through the inhibition of carbonic anhydrases expressed in Vibrio cholerae (VchCAα, VchCAβ, and VchCAγ). Therefore, we focused our interest on the exploitation of sulfonamides as VchCA inhibitors. We planned to design and synthesize new benzenesulfonamides based on our knowledge of the VchCA catalytic site. The synthesized compounds were tested thus collecting useful SAR information. From our investigation, we identified new potent VchCA inhibitors, some of them displayed high affinity toward VchCAγ class, for which few inhibitors are currently reported in literature. The best interesting VchCAγ inhibitor (S)-N-(1-oxo-1-((4-sulfamoylbenzyl)amino)propan-2-yl)furan-2-carboxamide (40) resulted more active and selective inhibitor when compared with acetazolamide (AAZ) as well as previously reported VchCA inhibitors.

Synthesis and Quantitative Structure-activity Relationships Study for Arylpropenamide Derivatives as Inhibitors of Hepatitis B Virus Replication

A series of new arylpropenamide derivatives containing different aryl groups were synthesized, characterized, and evaluated for their anti-hepatitis B virus (HBV) activities. A new high accuracy QSAR model of arylpropenamide was constructed based on a more completely activities data and calculation parameter. The 2D-QSAR equations, by using DFT and multiple linear regression analysis methods, revealed that higher value of thermal energy (TE) and lower entropy (S?) increase the anti-HBV activities of the arylpropenamide molecules. Predictive 3D-QSAR models were established by SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction.

Ruthenium hydride catalyzed direct oxidation of alcohols to carboxylic acids via transfer hydrogenation: Styrene oxide as oxygen source

Direct oxidation of alcohols to carboxylic acids using styrene epoxide as oxidant in the presence of [RuHCl(CO)(PPh3)3] complex as catalyst is reported. By this catalytic system, a variety of primary alcohols including substituted benzyl alcohols as well as linear ones were directly converted into carboxylic acids in good to excellent yields. Georg Thieme Verlag Stuttgart · New York.

Direct oxidation of alcohols to carboxylic acids over ruthenium hydride catalyst with diphenyl sulfoxide oxidant

In the present work, a new method for the synthesis of carboxylic acids over ruthenium hydride catalyst is reported. Direct oxidation of alcohols to their corresponding carboxylic acids with diphenyl sulfoxide oxidant over RuHCl(CO)(PPh3)3 catalyst was investigated. Mild reaction conditions, short reaction times and excellent yields make this method as an appealing way for preparation of carboxylic acids.

A convenient method for synthesis of 5-chloro-2-aryloxazole-4-carbaldehyde with vilsmeier reagent

A convenient method for synthesis of 5-chloro-2-aryloxazole-4-carbaldehyde 3 in moderate to good yields had been developed via the Vilsmeier reaction of readily available N-arylglycine 2 at 100 °C, provided a novel route for the construction of nitrogen heterocycles. A series of these compounds were synthesized by this method and optimization of conditions was performed. The Japan Institute of Heterocyclic Chemistry.

Structural effects of N-aromatic acyl-amino acid conjugates on their deconjugation in the cecal contents of rats: Implication in design of a colon-specific prodrug with controlled conversion rate at the target site

N-aromatic acyl-amino acid conjugates possess a colon-targeted property, implying that such conjugates are stable and are not absorbable until reaching the large intestine in which they are microbially converted (hydrolysed) to the parent drugs that are therapeutically active. To investigate the structural effect of N-aromatic acyl-amino acid conjugates on the large intestinal deconjugation, the hydrolysis of various N-aromatic acyl-amino acid conjugates was examined in the cecal contents. On incubation of conjugates with glycine,d or/andl forms of alanine or phenylalanine in the cecal contents, the conjugates withd amino acids were not hydrolysed. The other conjugates are susceptible to the hydrolysis, the rates of which decreased as the size of the substituent on the 2-position of the amino acids increased. The conjugates with alkyl analogs (2-4 carbons) of glycine and taurine were resistant to the hydrolysis, while taurine- and glycine-conjugates were hydrolysed effectively. The hydrolysis of N-aromatic acyl-glycine conjugates was enhanced by para-substitution of electron withdrawing groups on the aromatic acyl moiety and vice versa for electron-donating groups. While a methyl, methoxy or chloro group on the ortho-position retarded the hydrolysis, a hydroxyl group on the position accelerated it. Our data may provide useful information for the design of a colon-specific prodrug with controlled conversion rate in the large intestine.

Substituents effect on the erlenmeyer-ploechl reaction: Understanding an observed process reaction time

A systematic study on hippuric acid substituents was performed in order to better understand the influence of stereoelectronic factors on the Erlenmeyer reaction rate. In addition, two reaction systems were evaluated: Huenig's base solvent free conditions and catalytic sodium acetate in 2-methyl-THF. The effect on reaction rate of electron withdrawing and electron donating groups are reported. Specifically, the study led to the conclusion that stereoelectronic factors have significant influence in one of our key Erlenmeyer reaction by affecting its reaction rate.

Inhibitors of Diacylglycerol Acyltransferase

Provided herein are amides containing at least a four ring structure, which are inhibitors of diacylglycerol acyltransferase and are useful for the treatment of diseases such as, for example, obesity, type II diabetes mellitus and metabolic syndrome.

Complementarity between a docking and a high-throughput screen in discovering new cruzain inhibitors

Virtual and high-throughput screens (HTS) should have complementary strengths and weaknesses, but studies that prospectively and comprehensively compare them are rare. We undertook a parallel docking and HTS screen of 197861 compounds against cruzain, a thiol protease target for Chagas disease, looking for reversible, competitive inhibitors. On workup, 99% of the hits were eliminated as false positives, yielding 146 well-behaved, competitive ligands. These fell into five chemotypes: two were prioritized by scoring among the top 0.1% of the docking-ranked library, two were prioritized by behavior in the HTS and by clustering, and one chemotype was prioritized by both approaches. Determination of an inhibitor/cruzain crystal structure and comparison of the high-scoring docking hits to experiment illuminated the origins of docking false-negatives and false-positives. Prioritizing molecules that are both predicted by docking and are HTS-active yields well-behaved molecules, relatively unobscured by the false-positives to which both techniques are individually prone.