10147-71-4

Usage

Uses

Used in Pharmaceutical Industry:
ALPHA-CHLORO-3-NITROACETANILIDE is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new medications. Its analgesic and anti-inflammatory properties make it particularly valuable in the creation of pain relief and anti-inflammatory drugs.
Used in Dye Industry:
In the dye industry, ALPHA-CHLORO-3-NITROACETANILIDE serves as a crucial intermediate in the production of dyes. Its chemical structure allows for the creation of a range of colorants used in various applications, including textiles, plastics, and printing inks.

InChI:InChI=1/C10H9ClF3NO/c11-5-4-9(16)15-8-3-1-2-7(6-8)10(12,13)14/h1-3,6H,4-5H2,(H,15,16)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 99-09-2 3-nitro-aniline 
• 88-74-4 2-nitro-aniline 
• 6283-25-6 H₂NC₆H₃(Cl)NO₂ 
• 75-36-5 acetyl chloride 

Downstream Products

• 35763-43-0 N-(3-nitrophenyl)-2-(piperidin-1-yl)acetamide 
• 294193-71-8 N,N-dimethyl-glycine-(3-nitro-anilide) 
• 137813-84-4 2-(diethylamino)-N-(3-nitrophenyl)acetamide 
• 16231-13-3 diethoxythiophosphorylsulfanyl-acetic acid-(3-nitro-anilide) 
• 331981-25-0 thiocyanato-acetic acid-(3-nitro-anilide) 
• 108086-43-7 N-(3-Nitro-phenyl)-2-(4-oxo-4H-quinazolin-3-yl)-acetamide 
• 132659-17-7 2-[N'-(4-Hydroxy-6-methyl-pyrimidin-2-yl)-hydrazino]-N-(3-nitro-phenyl)-acetamide 
• 139438-03-2 2-[5-(4-{[1-(1H-Indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(3-nitro-phenyl)-acetamide 
• 139438-09-8 2-[4-(4-Chloro-phenyl)-5-(4-{[1-(1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(3-nitro-phenyl)-acetamide 
• 139438-14-5 N-(3-Nitro-phenyl)-2-[4-phenyl-5-(4-{[1-(2-phenyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetamide 
• 139438-18-9 2-[4-(4-Chloro-phenyl)-5-(4-{[1-(2-phenyl-1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(3-nitro-phenyl)-acetamide 
• 76809-65-9 2-iodo-N-(m-nitrophenyl)acetamide 
• 481038-62-4 2-benzyl-4-[(3-nitro-phenylcarbamoyl)-methyl]-piperazine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of novel 1,2,3-triazoles bearing 2,4 thiazolidinediones conjugates and their biological evaluation

Searching for new active molecules against M. Bovis BCG and Mycobacterium tuberculosis (MTB) H37Ra, a focused of 1,2,3-triazoles-incorporated 2,4 thiazolidinedione conjugates have been efficiently prepared via a click chemistry approach cyclocondensation of 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4), aryl aldehyde (5a–l), and mercapto acetic acid (6) with good to promising yields. The newly synthesized compounds were tested against drug-sensitive MTB and BCG. In particular, compounds 8g, 8h, 8j and 8l are highly potent against both the strains with IC90 values in the range of 1.20–2.70 and 1.24–2.65?μg/mL, respectively. Based on the results from the antitubercular activity, SAR for the synthesized series has been developed. Most of the active compounds were non-cytotoxic against MCF-7, HCT 116 and A549 cell lines. Most active compounds were having a higher selectively index, which suggested that these compounds were highly potent.

Design, synthesis and antiproliferative evaluation of novel disulfides containing 1,3,4-thiadiazole moiety

A series of novel disulfides containing 1,3,4-thiadiazole moiety were designed, synthesized, and the structures of all products were identified by spectral data (IR, NMR, and high resolution (HR)-MS). Their in vitro antiproliferative activities were evalu

Synthesis, Antimicrobial Evaluation, and Docking Studies of Substituted Acetylphenoxymethyl-triazolyl-N-phenylacetamides

A series of molecules containing acetylphenoxymethyl, triazole, and N-phenylacetamide moieties were synthesized via the click chemistry approach. All the synthesized compounds were screened for their antimicrobial activities in vitro. The synthesized compounds 8a, 8b, 8m, and 8n showed better activities. We further performed exploratory docking studies to gain some insight regarding the molecular mechanism of antibacterial action of these compounds that could guide further structure-activity relationship (SAR) studies. We examined the interaction of the most active compound with DNA gyrase (pdb id:1KZN). Based on antimicrobial and docking studies, the compounds 8a, 8b, 8m, and 8n were identified as potential antimicrobial agents.

Synthesis and anti-leishmanial evaluation of 1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline derivatives against Leishmania infantum

In the present study, antileishmanial activity of sixteen novel series of tetrahydro-β-carboline derivatives against transgenic infrared fluorescent Leishmania infantum strain has been reported. Among these reported analogues, most of the compounds exhibited potent inhibition against both promastigote (IC50from 1.99?±?1.40 to 20.69?±?0.95?μM) and amastigote (IC50from 0.67?±?0.05 to 4.16?±?0.008?μM) forms of L.?infantum. Moreover, compound 7l, displayed most potent and selective inhibition of parasite amastigote form with IC500.67?±?0.05?μM, selectivity index >298.5 and was comparable with standard drug amphotericin B. From this study, a new class of tetrahydro-β-carboline derivatives with potent antileishmanial activity was identified and it needs further extensive study to optimize the lead molecules to win the battle against severe and neglected disease leishmaniasis.

Benzylidene thiazolidinediones: Synthesis, in vitro investigations of antiproliferative mechanisms and in vivo efficacy determination in combination with Imatinib

Thiazolidinedione (TZD) has been an interesting scaffold due to its proven antidiabetic activity and encouraging findings in anticancer drug discovery. We synthesised benzylidene thiazolidinedione derivatives which exhibited excellent antiproliferative effects in chronic myeloid leukemic cells K562 and the most active compounds 3t and 3x had GI50 value of 0.9 and 0.23 μM respectively. Both the compound was found to arrest the growth of K562 cells in G0/G1 phase in a time and dose dependent manner. Further, western blot analysis revealed that 3t and 3x could also inhibit the expression of cell proliferation markers, PCNA and Cyclin D1 and compound 3x up-regulated apoptosis markers, cleaved PARP1 and activated caspase 3, which could be a possible mechanism for the excellent antiproliferative effects exhibited by these compounds. In vitro combination studies of 3t and 3x with Imatinib found to potentiate the antitumor effects of Imatinib. Further in vivo efficacy in K562 xenografts, of 3t and 3x alone and in combination with Imatinib was found to be promising and far better than control group and combination treatment was found to be more effective as compared to only Imatinib treated or test compound treated animals. Thus, our findings suggest that these compounds are promising antitumor agents and could help to enhance the anticancer effects of Imatinib and other tyrosine kinase inhibitors, when used in combination.

Synthesis and bioactivity of some novel 5-arylmethylideneamino-1,3,4- thiadiazole-2-ylthioacetanilide derivatives

Some novel of 5-arylmethylideneamino-1,3,4-thiadiazole-2-ylsulfanyl acetamide derivatives were synthesized by the S-alkylation of 5-arylmethylideneamino-2-mercapto-1,3,4-thiadiazoles with chloroacetyl anilide under solid-liquid phase transfer catalysis us

Structure-based design, synthesis, and biological evaluation of isatin derivatives as potential glycosyltransferase inhibitors

Peptidoglycan glycosyltransferase (PGT) has been shown to be an important pharmacological target for the inhibition of bacterial cell wall biosynthesis. Structure-based virtual screening of about 3 000 000 commercially available compounds against the crystal structure of the glycosyltransferase (GT) domain of the Staphylococcus aureus penicillin-binding protein 2 (S. aureus PBP2) resulted in identification of an isatin derivative, 2-(3-(2-carbamimidoylhydrazono)-2-oxoindolin-1-yl)-N-(m-tolyl)acetamide (4) as a novel potential GT inhibitor. A series of 4 derivatives were synthesized. Several compounds showed more active antimicrobial activity than the initial hit compound 4, in particular 2-(3-(2-carbamimidoylhydrazono)-2-oxoindolin-1-yl)-N-(3-nitrophenyl)acetamide (4l), against Gram-positive Bacillus subtilis and S. aureus with MIC values of 24 and 48 lg/mL, respectively. Saturation transfer difference (STD) NMR study revealed that there is a binding contact between 4l and the GT domain of S. aureus PBP2. Competitive STD-NMR further proved that 4l and moenomycin A bind to GT domain in a competitive manner. Molecular docking study suggests a potential binding pocket of 4l in the GT domain of S. aureus PBP2. Taken together, compound 4l would provide a new scaffold for further development of potent GT inhibitors.

Design, synthesis, antibacterial and quorum quenching studies of 1,2,5-trisubstituted 1,2,4-triazoles

Abstract: In view of discovering novel bioactive molecules, 1-phenyl-1H-2-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-3-(N-aryl-carbamoylmethylthio)-1,2,4-triazoles (8a–n) were designed and synthesized in good yield. Preliminary antibacterial activity was tested against Chromobacterium violaceum and Xanthomonas campestris pv. Campestris (Xcc). Out of 14 derivatives, compound 8g selectively possessed antibacterial activity against C. violaceum. Further derivatives that possessed an electron-withdrawing group and halogen atoms in N-phenylacetamide moiety were moderately active against Xcc (plant pathogen). After observing the reduction of violacein production through plate assay, compounds 8a, 8c, 8h, 8i and 8m were subjected to quantification of quorum sensing inhibition. Compounds with the electron-withdrawing group in N-phenylacetamide moiety showed admirable activity with > 80% inhibition of violacein. Mainly compound 8c which was inactive against the growth of bacteria were identified as excellent QSI which could be a lead compound for further development. Graphic abstract: One of the best approaches to acquire anti-virulence strategies and new direction for the discovery of antibacterial drugs[Figure not available: see fulltext.]

Design, synthesis and biological evaluation of novel thienylpyridyl-and thioether-containing acetamides and their derivatives as pesticidal agents

Referring to the structural information of the “hit” compound A from the reported pharmacophore-based virtual screening, a series of novel thienylpyridyl-and thioether/sulfoxide/ sulfone-containing acetamide derivatives have been designed and synthesized.

Synthesis, pharmacological evaluation, and in-silico studies of thiophene derivatives

The relevance of Retinoic acid receptor-related orphan receptors in cancer progression has sparked interest in developing multifunctional therapeutics. In the search for potentially active novel compounds with anticancer characteristics, the Gewald reaction was employed to develop different thiophene derivatives (8a–8i). Physicochemical and spectroanalytical investigations verified the molecular structures of the synthesized derivatives. Using an in vitro primary anticancer assay, NCI chose all of the synthesized molecules as prototypes and assessed their anticancer efficacy against a panel of various cancer cell lines representing nine distinct neoplasms. The compounds were found to have a wide range of anticancer activity. Following significant anticancer efficacy against all cell lines in the initial screening, compound 8e was chosen for a five-dose test. Compound 8e inhibited growth at concentrations ranging from 0.411 to 2.8 μM. The antioxidant activity of the compounds was further evaluated using the radical scavenging action of the stable DPPH free radical. In comparison to Ascorbic Acid, compounds 8e and 8i showed outstanding antioxidant activity, while the remaining compounds in the series demonstrated acceptable antioxidant activity. In a molecular docking investigation, 8e demonstrated excellent docking scores inside the binding pocket of the specified pdb-id (6q7a), complementing the results of anticancer screening. Based on our results, novel ethyl 5-acetyl-2-amino-4-methylthiophene-3-carboxylate derivatives could be useful in the development of potential anticancer treatments.