82525-64-2

Basic information

• Product Name: 4-(2-Chloro-acetylamino)-benzoic acid methyl ester
• Synonyms: 4-(2-Chloro-acetylamino)-benzoic acid methyl ester;Nsc39579;4-[(2-chloro-1-oxoethyl)amino]benzoic acid methyl ester;CBDivE_004303;methyl 4-(2-chloroethanoylamino)benzoate;methyl 4-[(2-chloroacetyl)amino]benzoate;SBB004508;ZINC00123972
• CAS NO: 82525-64-2
• Molecular Formula: C₁₀H₁₀ClNO₃
• Molecular Weight: 227.65
• Mol File: 82525-64-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 413.2°C at 760 mmHg
• Flash Point: 203.7°C
• Appearance: /
• Density: 1.325g/cm³
• Vapor Pressure: 4.89E-07mmHg at 25°C
• Refractive Index: 1.579
• CAS DataBase Reference: 4-(2-Chloro-acetylamino)-benzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-Chloro-acetylamino)-benzoic acid methyl ester(82525-64-2)
• EPA Substance Registry System: 4-(2-Chloro-acetylamino)-benzoic acid methyl ester(82525-64-2)

Safety Data

• Hazardous Substances Data: 82525-64-2(Hazardous Substances Data)

Usage

Chemical compound

4-(2-Chloro-acetylamino)-benzoic acid methyl ester

Common uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Derivation

Derived from benzoic acid; contains a chlorine atom and an acetylamino group

Health risks

Should be handled with caution as it may pose health risks if not properly managed

Safety protocols

Important to follow safety protocols and use appropriate protective equipment when working with this compound

InChI:InChI=1/C10H10ClNO3/c1-15-10(14)7-2-4-8(5-3-7)12-9(13)6-11/h2-5H,6H2,1H3,(H,12,13)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 619-45-4 4-methoxycarbonyl aniline 
• 150-13-0 4-amino-benzoic acid 

Downstream Products

• 1013663-50-7 C₂₇H₂₅N₃O₆S 
• 1013663-55-2 C₂₇H₂₅N₃O₆S 
• 1215289-42-1 N-(4-carbomethoxyphenyl)-2-[4-oxo-2-(4-methoxyphenyl)pyrimido[1,2-a]benzimidazol-10(4H)-yl]-acetamide 
• 695194-13-9 2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(4-methoxycarbonylphenyl)acetamide 
• 1429653-58-6 C₂₄H₃₄N₂O₄Si 
• 1426446-38-9 (E)-methyl 4-(3-(2-azidophenyl)acrylamido)benzoate 
• 1426446-59-4 Cl^(1-)*C₂₈H₂₅NO₃P⁽¹⁺⁾ 
• 1393643-22-5 C₂₁H₂₃N₅O₃S 
• 63450-84-0 methyl 4-aminobenzoate hydrochloride 
• 153720-00-4 methyl 4-[(aminoacetyl)amino]benzoate 
• 100876-25-3 4-[(N,N-diethyl-glycyl)-amino]-benzoic acid methyl ester 

Relevant articles and documents

Highly Potent and Selective Butyrylcholinesterase Inhibitors for Cognitive Improvement and Neuroprotection

Butyrylcholinesterase (BChE) has been considered as a potential therapeutic target for Alzheimer's disease (AD) because of its compensation capacity to hydrolyze acetylcholine (ACh) and its close association with Aβ deposit. Here, we identified S06-1011 (hBChE IC50 = 16 nM) and S06-1031 (hBChE IC50 = 25 nM) as highly effective and selective BChE inhibitors, which were proved to be safe and long-acting. Candidate compounds exhibited neuroprotective effects and the ability to improve cognition in scopolamine- and Aβ1-42 peptide-induced cognitive deficit models. The best candidate S06-1011 increased the level of ghrelin, a substrate of BChE, which can function as improving the mental mood appetite. The weight gain of the S06-1011-treated group remarkably increased. Hence, BChE inhibition not only plays a protective role against dementia but also exerts a great effect on treating and nursing care.

Discovery and evaluation of new compounds targeting ribosomal protein S1 in antibiotic-resistant Mycobacterium Tuberculosis

The emergence of antibiotic-resistant Mycobacterium Tuberculosis (Mtb) infections compels new treatment strategies, of which targeting trans-translation is promising. During the trans-translation process, the ribosomal protein S1 (RpsA) plays a key role, and the Ala438 mutant is related to pyrazinamide (PZA) resistance, which shows its effects after being hydrolysed to pyrazinoic acid (POA). In this study, based on the structure of the RpsA C-terminal domain (RpsA-CTD) and POA complex, new compounds were designed. After being synthesized, the compounds were tested in vitro with saturation transfer difference (STD), fluorescence quenching titration (FQT) and chemical shift perturbation (CSP) experiments. Finally, six of the 17 new compounds have high affinity for both RpsA-CTD and its Ala438 deletion mutant. The active compounds provide new choices for targeting trans-translation in Mtb, and the analysis of the structure-activity relationships will be helpful for further structural modifications based on derivatives of 2-((hypoxanthine-2-yl)thio)acetic acid and 2-((5-hydroxylflavone-7-yl)oxy)acetamide.

Structural optimization of N1-aryl-benzimidazoles for the discovery of new non-nucleoside reverse transcriptase inhibitors active against wild-type and mutant HIV-1 strains

Non-nucleoside reverse transcriptase inhibitors (NNRTIs) are recommended components of preferred combination antiretroviral therapies used for the treatment of human immunodeficiency virus (HIV) infection. These regimens are extremely effective in suppressing virus replication. Recently, our research group identified some N1-aryl-2-arylthioacetamido-benzimidazoles as a novel class of NNRTIs. In this research work we report the design, the synthesis and the structure–activity relationship studies of new compounds (20–34) in which some structural modifications have been introduced in order to investigate their effects on reverse transcriptase (RT) inhibition and to better define the features needed to increase the antiviral activity. Most of the new compounds proved to be highly effective in inhibiting both RT enzyme at nanomolar concentrations and HIV-1 replication in MT4 cells with minimal cytotoxicity. Among them, the most promising N1-aryl-2-arylthioacetamido-benzimidazoles and N1-aryl-2-aryloxyacetamido-benzimidazoles were also tested toward a panel of single- and double-mutants strain responsible for resistance to NNRTIs, showing in vitro antiviral activity toward single mutants L100I, K103N, Y181C, Y188L and E138K. The best results were observed for derivatives 29 and 33 active also against the double mutants F227L and V106A. Computational approaches were applied in order to rationalize the potency of the new synthesized inhibitors.