10147-70-3

Usage

Uses

Used in Organic Chemistry Research:
ALPHA-CHLORO-2-NITROACETANILIDE is used as a research compound for its role in facilitating various organic reactions. It is particularly valuable in the synthesis of complex chemical compounds, contributing to the advancement of organic chemistry knowledge and the development of new materials and substances.
Used in Laboratory Settings:
In laboratory environments, ALPHA-CHLORO-2-NITROACETANILIDE is used as a reagent in chemical experiments. Its stable properties make it suitable for a range of applications, including the study of reaction mechanisms and the development of new synthetic pathways.

InChI:InChI=1/C8H7ClN2O3/c9-5-8(12)10-6-3-1-2-4-7(6)11(13)14/h1-4H,5H2,(H,10,12)

Upstream product

• 88-74-4 2-nitro-aniline 
• 79-04-9 chloroacetyl chloride 
• 99-09-2 3-nitro-aniline 
• 62-53-3 aniline 
• 587-65-5 N-chloroacetyl-aniline 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 

Downstream Products

• 100138-78-1 pyrrolidino-acetic acid-(2-nitro-anilide) 
• 35204-11-6 N-(2-nitro-phenyl)-2-piperidin-1-yl-acetamide 
• 35204-30-9 N,N-diethyl-glycine-(2-nitro-anilide) 
• 855277-06-4 4-{[(2-nitro-phenylcarbamoyl)-methyl]-amino}-benzoic acid ethyl ester 
• 35204-33-2 N-(2-aminophenyl)-2-(N-methyl-N-n-butylamino)acetamide 
• 63238-21-1 [3-(2-nitro-phenyl)-4-oxo-thiazolidin-2-ylidene]-cyanamide 
• 757879-84-8 N,N-dibutyl-glycine-(2-amino-anilide) 
• 134268-72-7 2-(2'-Hydroxy-biphenyl-2-yloxy)-N-(2-nitro-phenyl)-acetamide 
• 88-74-4 2-nitro-aniline 
• 79-11-8 chloroacetic acid 
• 76809-66-0 2-iodo-N-(o-nitrophenyl)acetamide 
• 108086-42-6 N-(2-Nitro-phenyl)-2-(4-oxo-4H-quinazolin-3-yl)-acetamide 
• 132659-16-6 2-[N'-(4-Hydroxy-6-methyl-pyrimidin-2-yl)-hydrazino]-N-(2-nitro-phenyl)-acetamide 

Relevant academic research and scientific papers

Design, synthesis, bioactivity, and computational studies of some morpholine-clubbed coumarinyl acetamide and cinnamide derivatives

Abstract: The novel derivatives of morpholine-clubbed 3-substituted coumarinyl acetamide and cinnamide derivatives 5a–5j and 6a–6j have been synthesized via various 2-chloro-N-phenyl acetamide and cinnamoyl chloride derivatives, respectively. The required motif has been generated through Vilsmeier–Haack reaction on 4-hydroxycoumarin annelation of morpholine followed by imine formation and subsequently condensation with various 2-chloro-N-phenylacetamide and cinnamoyl chloride to furnish the desired molecule. The synthesized molecules were characterized by various spectroscopic methods viz IR, 1H NMR, 13C NMR. Their antimicrobial activities against various strains of bacteria and fungi have been evaluated, and computational studies have also been performed for all the newly synthesized analogs. Graphical Abstract: [Figure not available: see fulltext.].

Synthesis and in vitro kinetic study of novel mono-pyridinium oximes as reactivators of organophosphorus (OP) inhibited human acetylcholinesterase (hAChE)

A series of mono pyridinium oximes linked with arenylacetamides as side chains were synthesized and their in vitro reactivation potential was evaluated against human acetylcholinesterase (hAChE) inhibited by organophosphorus inhibitors (OP) such as sarin, VX and tabun. The reactivation data of the synthesized compounds were compared with those obtained with standard reactivators such as 2-PAM and obidoxime. The dissociation constant (KD) and specific reactivity (kr) of the oximes were also determined by performing reactivation kinetics against OP inhibited hAChE. Among the synthesized compounds, oximes 1-(2-(4-cyanophenylamino)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridinium chloride (12a) and 4-((hydroxyimino)methyl)-1-(2-(4-methoxyphenylamino)-2-oxoethyl)pyridinium chloride (2a) were found most potent reactivators for hAChE inhibited by sarin. In case of VX inhibited hAChE majority of the oximes have shown good reactivation efficacies. Among these oximes 1-(2-(benzylamino)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridinium chloride (18a), 4-((hydroxyimino)methyl)-1-(2-(4-(methoxycarbonyl)phenylamino)-2-oxoethyl)pyridinium-chloride (14a) and 12a were found to surpass the reactivation potential of 2-PAM and obidoxime. However, the synthesized oximes showed marginal reactivation efficacies in case of tabun inhibited hAChE. The pKa value of the oximes were determined and correlated with their observed reactivation potential.

Design, synthesis, and QSAR study of novel 2-(2,3-dioxo-2,3- dihydro-1H-indol-1-yl)-N-phenylacetamide derivatives as cytotoxic agents

This study deals with the synthesis of novel 2- (2,3-dioxo-2,3-dihydro-1H- indol-1-yl)-N-phenylacetamide derivatives (6a-j) from isatin (3) and 5,7-dibromoisatin (4). All newly synthesized compounds were characterized using IR, 1H NMR, MS, and elemental analysis followed by evaluation of their cytotoxic activity by XTT assay on breast cancer cell line MCF-7 and non-cancer African green monkey cell line VERO. Correlation study for QSAR and in vitro assay was performed. The outcomes indicated that electron withdrawing substitutions at para position of phenyl ring and 5, 7 positions of isatin ring and increasing lipophilicity of the compound increased the cytotoxic activity. The 2-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)- N-(4-nitrophenyl)acetamide (6b) was found to be the most active compound in the series and demonstrated higher selectivity toward MCF-7 cell line. The IC50 values were 1.96 and 1.90 lM for test compound (6b) and vinblastin (reference drug), respectively. This indicates compound (6b) may possess equipotent cytotoxic activity to vinblastine. The compound (6b) is particularly promising, since it could kill cancer cells 19-20 times more effectively than the non-cancer cells. This property of (6b) may enable us to effectively control tumors with low side effects. Hence, we propose that 2-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1Hindol- 1-yl)-N-(4-nitrophenyl)acetamide may be used as lead for further development. Springer Science+Business Media, LLC 2010.

Design, synthesis, biological evaluation, and molecular modeling of coumarin-piperazine derivatives as acetylcholinesterase inhibitors

Acetylcholinesterase (AChE) is an important drug target for the treatment of Alzheimer's disease. A novel series of coumarin-piperazine derivatives were synthesized and their potency to inhibit human AChE enzyme (hAChE) was studied. All the final compounds were characterized by infrared, 1H NMR, 13C NMR, and elemental analysis. Docking experiments of the designed coumarin-piperazine derivatives were carried out in order to compare the theoretical and experimental binding affinities toward hAChE, to delineate the inhibitory mechanism. Subsequently, a structure-activity relationship (SAR) study using the molecular field method showed that the hydrophobic field and positive charge center conferred by the coumarin and piperazine moieties demonstrated an inhibitory mechanism. Among the compounds tested, 3f, 3j, and 3m were found to be the most potent inhibitors of hAChE. New coumarin-piperazine derivatives were synthesized and studied for their potency to inhibit the human acetylcholinesterase enzyme (hAChE). Docking experiments were carried out in order to compare the theoretical and experimental binding affinities toward hAChE. The hydrophobic field and positive charge center conferred by the coumarin and piperazine moieties demonstrated an inhibitory mechanism.

Evaluation of glycolamide esters of indomethacin as potential cyclooxygenase-2 (COX-2) inhibitors

A number of novel indomethacin glycolamide esters were synthesized and tested for their cyclooxygenase (COX-1 and COX-2) inhibition properties in vitro. Many of these compounds proved to be selective COX-2 inhibitors, and subtle structural changes in the substituents on the glycolamide ester moiety altered the inhibitory properties as well as potencies significantly. Their in vitro data were rationalized through molecular modeling studies. Few of them displayed anti-inflammatory activity in vivo. Compound 32, [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2-morpholin-4-yl-2-oxo ethyl ester, was identified as a promising compound in this class and its good anti-inflammatory activity was demonstrated in the in vivo model.

Synthesis, bioevaluation and molecular docking study of new piperazine and amide linked dimeric 1,2,3-triazoles

In search of more potent new antitubercular agents, a library of novel piperazine tethered dimeric 1,2,3-triazoles were designed by assembling 1,2,3-triazoles and piperazine in a single molecular architectural framework. The titled compounds (3a–m) were synthesized by 1,3-dipolar cycloaddition of 1,4-di(prop-2-yn-1-yl)piperazine (1) and various azides (2a–m) using click chemistry approach with good yields. All the synthesized compounds (3a–m) have been screened for their in vitro antitubercular, antifungal and antioxidant activities against their respective strains. Among them, 3b, 3d, and 3i have revealed promising antitubercular activity against Mycobacterium tuberculosis (Mtb) H37Rv with MIC 12.5 μg/mL. Molecular docking results provided well-clustered solutions to the mode of binding for these molecules into the active site of Mtb enoyl reductase (InhA). In addition to this, most of synthesized compounds were found to have potential antifungal as well as antioxidant activity.

Synthesis and antimicrobial activity of novel thienopyrimidine linked rhodanine derivatives

This work presents the preparation of a new series of N-(substituted phenyl)-2-(4-oxo-5-(4-(thieno[2,3-d]-pyrimidin-4-yloxy)benzylidene)-2-thioxothiazolidin-3-yl)acetamide derivatives (8a-8l). A condensation reaction of thienopyrimidin-2-thioxothiazolidin

New 4,5-diphenylimidazole-acetamide-1,2,3-triazole hybrids as potent α-glucosidase inhibitors: synthesis, in vitro and in silico enzymatic and toxicity evaluations

Herein, a new series of 4,5-diphenylimidazole-acetamide-1,2,3-triazole hybrids as potent α-glucosidase inhibitors was designed and synthesized. All the synthesized compounds exhibited excellent inhibition potencies (IC50 values = 55.6–149.2 μM)

Azolylthioacetamide: A highly promising scaffold for the development of metallo-β-lactamase inhibitors

A new scaffold, azolylthioacetamide, was constructed and assayed against metallo-β-lactamases (MβLs). The obtained molecules specifically inhibited MβL ImiS, and 1c was found to be the most potent inhibitor, with a Ki = 1.2 μM using imipenem as substrate. Structure-activity relationships reveal that the aromatic carboxyl improves inhibitory activity of the inhibitors, but the aliphatic carboxyl does not. Compounds 1c-d and 1h-i showed the best antibacterial activities against E. coli BL21(DE3) cells producing CcrA or ImiS, resulting in 32- and 8-fold reduction in MIC values, respectively; 1c and 1f-j resulted in a reduction in MIC against P. aeruginosa. Docking studies revealed that 1a, 1c, and 1d fit tightly into the substrate binding site of CphA as a proxy for ImiS with the aromatic carboxylate forming interactions with Lys224, the Zn(II) ion, the backbone of Asn233, and hydrophobic portions of the inhibitors aligning with hydrophobic patches of the protein surface.

Synthesis, and in vitro biological evaluations of novel naphthoquinone conjugated to aryl triazole acetamide derivatives as potential anti-Alzheimer agents

Alzheimer's disease is a neurodegenerative disorder that deteriorates mental ability. Two main cholinesterases named, acetylcholinesterase and butyrylcholinesterase are potential targets against Alzheimer's disease. Cholinesterase inhibitors have benefici