2564-04-7

Usage

Uses

Used in Agricultural Industry:
2-chloro-N-(3,4-dimethylphenyl)acetamide is used as a herbicide and nematocide for its ability to inhibit the growth of cells in the roots and shoots of plants, effectively preventing them from sprouting and growing. This makes it a valuable tool in controlling weeds in various crops and preventing sprouting in stored potatoes.
Used in Stored Potato Management:
2-chloro-N-(3,4-dimethylphenyl)acetamide is used as a sprout inhibitor for stored potatoes, ensuring that the potatoes remain in a dormant state and do not begin to sprout, which can affect their quality and marketability.

InChI:InChI=1/C10H12ClNO/c1-7-3-4-9(5-8(7)2)12-10(13)6-11/h3-5H,6H2,1-2H3,(H,12,13)

Upstream product

• 95-64-7 4-amino-o-xylene 
• 79-07-2 Chloroacetamide 
• 79-04-9 chloroacetyl chloride 
• 79-11-8 chloroacetic acid 

Downstream Products

• 102477-31-6 4-[(3,4-dimethyl-phenylcarbamoyl)-methyl]-piperazine-1-carboxylic acid benzyl ester 
• 109475-85-6 3-carbamoyl-1-[(3,4-dimethyl-phenylcarbamoyl)-methyl]-pyridinium; chloride 
• 3213-16-9 2-(diethylamino)-N-(3,4-dimethyl-phenyl)acetamide 
• 1239174-63-0 C₂₂H₂₅F₂N₅O₂ 
• 1016687-41-4 C₁₁H₁₆N₂O 
• 1031106-86-1 2-(3-benzyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl)-N-(3,4-dimethylphenyl)acetamide 
• 108850-30-2 morpholino-acetic acid-(3,4-dimethyl-anilide) 
• 133168-02-2 piperidino-acetic acid-(3,4-dimethyl-anilide) 
• 114402-15-2 pyrrolidino-acetic acid-(3,4-dimethyl-anilide) 
• 1160748-28-6 2-azido-N-(3,4-dimethyl-phenyl)-acetamide 

Relevant academic research and scientific papers

Design and synthesis of 2,4-dioxochroman-pyridinium-phenylacetamide derivatives as new anti-Alzheimer agents: in vitro and in silico studies

2,4-Dioxochroman-pyridinium-phenylacetamide derivatives 7a–n were synthesized and evaluated for their in vitro cholinesterase (ChE) inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Obtained results demonstrated that, among the synthesized compounds, two compounds, 7j and 7k, were more potent than the standard drug donepezil against BuChE and did not show cytotoxicity and carcinogenicity. Furthermore, through molecular modeling and molecular dynamic studies. we showed that these compounds can be located deep in the gorge cavity of BuChE and that they interacted with catalytic residues, acyl, and cholin-binding pockets of this enzyme. Support information.

Biology-Oriented Drug Synthesis (BIODS) Approach towards Synthesis of Ciprofloxacin-Dithiocarbamate Hybrids and Their Antibacterial Potential both in Vitro and in Silico

A novel series of ciprofloxacin-dithiocarbamate hybrids 7a?–?7l were designed, synthesized, and evaluated against Gram-positive and Gram-negative bacteria. A significant part of the title compounds showed considerable antibacterial activity against Gram-positive species. The most potent compound against Gram-positive bacteria was 2-chloro derivative 7h and the most potent derivative against Gram-negative bacteria was 3-chloro compound 7i. In?vitro antibacterial evaluation of compound 7h against clinically isolated bacteria methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-sensitive Staphylococcus aureus (MSSA) showed that this compound acted better than ciprofloxacin against the latter bacteria. Docking study of compound 7h in the active site of S.?aureus DNA gyrase revealed that this ciprofloxacin-dithiocarbamate derivative interacted with the main components of the active site of the enzyme.

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.]

Synthesis, biological evaluation, and structure-activity relationships of new tubulin polymerization inhibitors based on 5-amino-1,2,4-triazole scaffold

Based on our previous research, thirty new 5-amino-1H-1,2,4-triazoles possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities. Among them, compounds IIa, IIIh, and IIIm demonstrated significant antiproliferative activities against a panel of tumor cell lines, and the promising compound IIIm dose-dependently caused G2/M phase arrest in HeLa cells. Furthermore, analogue IIa exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 9.4 μM, and molecular modeling studies revealed that IIa formed stable interactions in the colchicine-binding site of tubulin, suggesting that 5-amino-1H-1,2,4-triazole scaffold has potential for further investigation to develop novel tubulin polymerization inhibitors with anticancer activity.

Synthesis of New Thieno[2,3-d]pyrimidines Containing a 1,2,3-Triazole Ring and Their Therapeutic Response in NCI-60 Cell Line Panel

Abstract: A series of new tetrahydro[1]benzothieno[2,3-d]pyrimidines containing a 1,2,3-triazole fragment linkedthrough an oxymethylene spacer have been synthesized by click reaction of4-(prop-2-yn-1-yloxy)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidines with various aryl and alkyl azides inthe presence of copper sulfate and sodium ascorbate as a catalyst. Thestructures of the synthesized compounds were characterized by variousspectroscopic techniques (1H and13C NMR, FT-IR, and mass spectrometry), and theirin vitro anticancer activity against NCI-60 human tumor cell lines wasevaluated. Among the compounds tested, N-(pyridine-3-yl)-acetamide derivative exhibited significantactivity against several cancer cell lines, including SF-539 (CNS cancer),HCT-116 (colon cancer), OVCAR-8 (ovarian cancer), PC-3 (prostate cancer), andCCRF-CEM (leukemia).

Synthesis and Anti-Inflammatory Properties of Substituted 5-(Tetrahydro-4-phenyl-2H-pyran-4-yl)-4H-1,2,4-triazole-3-thiols

Abstract: 5-(Tetrahydro-4-phenyl-2H-pyran-4-yl)-4H-1,2,4-triazole-3-thiol was synthesized by the reaction of 4-phenyltetrahydropyran-4-carbonyl chloride with thiosemicarbazide and subsequent cyclization of the resulting amide in the presence of KOH. The c

Design, Synthesis, and Bioactivity of α-Ketoamide Derivatives Bearing a Vanillin Skeleton for Crop Diseases

A series of novel α-ketoamide derivatives bearing a vanillin skeleton were designed and synthesized. Bioactivity tests on virus and bacteria were performed. The results indicated that some compounds exhibited excellent antitobacco mosaic virus (TMV) activities, such as compound 34 exhibited an inactivation activity of 90.1percent and curative activity of 51.8percent and compound 28 exhibited a curative activity of 54.8percent at 500 μg mL-1, which is equivalent to that of the commercial ningnanmycin (inactivation of 91.9percent and curative of 51.9percent). Moreover, the in vitro antibacterial activity test illustrated that compounds 2, 22, and 33 showed much higher activities than commercial thiodiazole copper, which could be used as lead compounds or potential candidates. The findings of transmission electron microscopy and molecular docking indicated that the synthesized compounds exhibited strong and significant binding affinity to the TMV coat protein and could obstruct the self-assembly and increment of TMV particles. This study revealed that α-ketoamide derivatives bearing a vanillin skeleton could be used as a novel potential pesticide for controlling the plant diseases.

Ultrasonic-Assisted Synthesis of Pyrazolo[3,4-d]pyrimidin-4-ol Tethered with 1,2,3-Triazoles and Their Anticancer Activity

Abstract: In the presents work synthesis and characterization of new heterocyclic derivatives containing pyrazolo[3,4-d]pyrimidine linkage with 1,4-disubstituted-1,2,3-triazoles via methylene-oxy group. The selected synthesized compounds were tested for their in-vitro anticancer activity against various cancer cell lines. Synthesis of compounds was done under ultrasonic-assisted Huisgen 1,3-dipolar cycloaddition reaction with good yields. Some of the newly synthesized compounds demonstrated good to moderate anticancer activity, most of compounds shows activity against renal cancer cell lines.

Discovery and optimization of 3,4,5-trimethoxyphenyl substituted triazolylthioacetamides as potent tubulin polymerization inhibitors

Based on our previous research, three series of new triazolylthioacetamides possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities and inhibition of tubulin polymerization. The most promising compounds 8b and 8j demonstrated more significant antiproliferative activities against MCF-7, HeLa, and HT-29 cell lines than our lead compound 6. Moreover, analogues 8f, 8j, and 8o manifested more potent antiproliferative activities against HeLa cell line with IC50 values of 0.04, 0.05 and 0.16 μM, respectively, representing 100-, 82-, and 25-fold improvements of the activity compared to compound 6. Furthermore, the representative compound, 8j, was found to induce significant cell cycle arrest at the G2/M phase in HeLa cell lines via a concentration-dependent manner. Meanwhile, compound 8b exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 5.9 μM, which was almost as active as that of CA-4 (IC50 = 4.2 μM). Additionally, molecular docking analysis suggested that 8b formed stable interactions in the colchicine-binding site of tubulin.

Side chain-functionalized aniline-derived ursolic acid derivatives as multidrug resistance reversers that block the nuclear factor-kappa B (NF-κB) pathway and cell proliferation

A series of inhibitors of NF-κB based on ursolic acid (UA) derivatives containing functionalized aniline or amide side chains were synthesized and evaluated for inhibition of NF-κB as well as their antitumor effects. These compounds exhibited significant inhibition activity toward NF-κB with IC50 values at micromolar concentrations in the NCI-H460 lung adenocarcinoma cell line. A docking study of the most active compound 5Y8 revealed key interactions between 5Y8 and the active site of NF-κB in which the functionalized amide moiety at the C-28 position and an ester group at the C-3 position were important for improving the activity. In particular, compound 5Y8 appeared to be the most potent compound against the NCI-H460 cell line, and displayed similar efficiency in drug-sensitive versus drug-resistant cancer cell lines, at least partly, by blocking the NF-κB signaling pathway and inducing apoptosis. Mechanistically, compound 5Y8 might trigger the apoptotic signaling pathway. Thus, the rational design of UA derivatives with functionalized aniline or amide side chains offers significant potential for the discovery of a new class of NF-κB inhibitors with the ability to induce apoptosis and reverse multidrug resistance in the NCI-H460 lung adenocarcinoma cell line.