96980-64-2

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Chloro-N-(chloroacetyl)-4-fluoroaniline is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 3-chloro-N-(chloroacetyl)-4-fluoroaniline is employed as a building block in the creation of compounds that protect crops from pests and diseases, enhancing agricultural productivity.
Used in Dye and Pigment Manufacturing:
3-Chloro-N-(chloroacetyl)-4-fluoroaniline is utilized as a precursor in the production of dyes and pigments, contributing to the coloration of textiles, plastics, and other materials.

InChI:InChI=1/C8H6Cl2FNO/c9-4-8(13)12-5-1-2-7(11)6(10)3-5/h1-3H,4H2,(H,12,13)

Upstream product

• 367-21-5 3-chloro-4-fluorophenylamine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 141079-24-5 N-(3-Chloro-4-fluoro-phenyl)-2-(4-chloro-3-methyl-phenoxy)-acetamide 
• 1018074-64-0 C₁₆H₁₀Cl₃F₂N₅OS 
• 1236306-18-5 N-(3-chloro-4-fluorophenyl)-2-(4-(4-(pyridin-4-ylmethyl)phthalazin-1-yl)piperazin-1-yl)acetamide 
• 1236306-31-2 N-(3-chloro-4-fluorophenyl)-2-(4-(4-benzylphthalazin-1-yl)piperazin-1-yl)acetamide 
• 553640-38-3 N-(3-chloro-4-fluorophenyl)-2-(4-formylphenoxy)acetamide 
• 1266715-54-1 (Z)-N-(3-chloro-4-fluorophenyl)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide 
• 1310561-78-4 N-(3-chloro-4-fluorophenyl)-2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide 
• 1310561-65-9 N-(3-chloro-4-fluorophenyl)-2-(4-((2,4,6-trioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide 
• 1304771-72-9 2-(2-methylquinoxalin-3-ylthio)-N-(3-chloro-4-fluorophenyl)acetamide 
• 1239174-65-2 C₂₀H₁₉ClF₃N₅O₂ 
• 1040320-69-1 C₉H₁₀ClFN₂O 
• 1384282-41-0 6,6'-bis{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-N,N'-diethyl-5,5'-dimethoxybiphenyl-2,2'-dicarboxamide 
• 1387000-08-9 N-(3-chloro-4-fluorophenyl)-2-(6-methoxy-2-oxo-2H-chromen-7-yloxy)acetamide 
• 881940-82-5 2-(3-chloro-4-fluorophenylimino)-5-(4-hydroxy-3-methoxybenzylidene)-4-thiazolidinone 

Relevant academic research and scientific papers

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

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.]

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)

Design, Synthesis, Antibacterial Activity, and Mechanisms of Novel 1,3,4-Thiadiazole Derivatives Containing an Amide Moiety

To discover novel antibacterial agents, a series of novel 1,3,4-thiadiazole derivatives containing an amide moiety were designed and synthesized, and their antibacterial activities were tested. Compound 30 was designed and synthesized according to the CoMFA model. Compound 30 exhibited higher antibacterial activities against Xanthomonas oryzae pv. oryzicola and Xanthomonas oryzae pv. oryzae, with EC50 values of 2.1 and 1.8 mg/L, respectively, which were superior to those of thiodiazole copper (99.6 and 92.5 mg/L). The protective and curative activities of compound 30 against rice bacterial leaf blight were 51.3 and 46.1%, respectively, which were better than those of thiodiazole copper (37.8 and 38.5%). The protective and curative activities of compound 30 against rice bacterial leaf streak were 45.9 and 40.5%, respectively, which were better than those of thiodiazole copper (36.2 and 31.1%). In addition, the protective activity of compound 30 against rice bacterial leaf streak was related to increased activities of related defense enzymes and upregulated the differentially expressed proteins of the glycolysis/gluconeogenesis pathway.

Design, synthesis and biological evaluation of novel 2,4-disubstituted quinazoline derivatives targeting H1975 cells via EGFR-PI3K signaling pathway

In order to find new and highly effective anti-tumor drugs with targeted therapeutic effects, a series of novel 4-aminoquinazoline derivatives containing N-phenylacetamide structure were designed, synthesized and evaluated for antitumor activity against four human cancer cell lines (H1975, PC-3, MDA-MB-231 and MGC-803) using MTT assay. The results showed that the compound 19e had the most potent antiproliferative activity against H1975, PC-3, MDA-MB-231 and MGC-803 cell lines. At the same time, compound 19e could significantly inhibit the colony formation and migration of H1975 cells. Compound 19e also arrested the H1975 cell cycle in the G1 phase and mediated cell apoptosis, promoted the accumulation of ROS in H1975 cells. Furthermore, compound 19e exerted antitumor effect in vitro by reducing the expression of anti-apoptotic protein Bcl-2 and increasing the pro-apoptotic protein Bax and p53. Mechanistically, compound 19e could significantly decreased the phosphorylation of EGFR and its downstream protein PI3K in H1975 cells. Which indicated that compound 19e targeted H1975 cell via interfering with EGFR-PI3K signaling pathway. Molecular docking showed that compound 19e could bind into the active pocket of EGFR. Those work suggested that compound 19e would have remarkable implications for further design of anti-tumor agents.

Novel vanillin derivatives containing a 1,3,4-thiadiazole moiety as potential antibacterial agents

In this study, thirty-four novel vanillin derivatives containing a 1,3,4-thiadiazole structure were obtained and their antibacterial activities were evaluated. The results indicate that most of the title compounds displayed inhibitory effects on Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc). Among them, compound 29 exhibited excellent antibacterial activities against Xoo and Xoc in vitro, with the EC50 values of 3.14 and 8.83 μg/mL, respectively, much superior to thiodiazole copper (87.03 and 108.99 μg/mL) and bismerthiazol (67.64 and 79.26 μg/mL). Under greenhouse condition, the protective efficiency of compound 29 against rice bacterial leaf blight was 49.34%, and curative efficiency was 40.96%. In addition, compound 29 can reduce the exopolysaccharides production of Xoo, increase the permeability of cell membrane and damage cell membrane.

Novel 2-(substituted phenyl Imino)-5-benzylidene-4-thiazolidinones as possible non-ulcerogenic tri-action drug candidates: synthesis, characterization, biological evaluation And docking studies

The present research was aimed at the synthesis and screening of 35 novel 2-(substituted phenyl imino)-5-benzylidene-4-thiazolidinones having different substitutions at imino phenyl and arylidene groups. The title compounds were synthesized by Knoevenagel

Substituted Aminoacetamides as Novel Leads for Malaria Treatment

Herein we describe the optimization of a phenotypic hit against Plasmodium falciparum based on an aminoacetamide scaffold. This led to N-(3-chloro-4-fluorophenyl)-2-methyl-2-{[4-methyl-3-(morpholinosulfonyl)phenyl]amino}propanamide (compound 28) with low-nanomolar activity against the intraerythrocytic stages of the malaria parasite, and which was found to be inactive in a mammalian cell counter-screen up to 25 μm. Inhibition of gametes in the dual gamete activation assay suggests that this family of compounds may also have transmission blocking capabilities. Whilst we were unable to optimize the aqueous solubility and microsomal stability to a point at which the aminoacetamides would be suitable for in vivo pharmacokinetic and efficacy studies, compound 28 displayed excellent antimalarial potency and selectivity; it could therefore serve as a suitable chemical tool for drug target identification.

Anti-proliferative activity, molecular modeling studies and interaction with calf thymus DNA of novel ciprofloxacin analogues

Abstract: In our pursuit to expand new potential anticancer leads, a series of eighteen novel 1-cyclopropyl-6-fluoro-4-oxo-7-(4-substituted piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid analogues have been synthesized, characterized and evaluated anti-proliferative activity against five human cancer cell lines such as A549 (lung cancer), Mia Paca (pancreatic cancer), HeLa (cervical cancer), MDA MB-231 (breast cancer), MCF-7 (breast cancer) and normal embryonic kidney?cell line (HEK) were carried out using MTT assay. Few of the synthesized analogues exhibited potent anticancer activity against the cancer cell lines at a lower concentration. The synthesized compounds showed the less toxic effect on normal human embryonic kidney?cell line (HEK) compared with doxorubicin. Noticeably, compound 3o exhibited potent activity against all five cancer cell lines compared with ciprofloxacin. Further study exposed that compound 3o could competently intercalate into calf thymus DNA to form 3o-DNA complex which might block DNA replication to apply anti-proliferative activity. Docking simulation studies supported by molecular interactions with DNA type II topoisomerase. These derivates can become lead structures for the development of potential anticancer drugs. Graphical Abstract: Eighteen CP analogues were synthesized and evaluated for anti-proliferative activity. The interactions with DNA topoisomerase II were supported by molecular docking studies. 3o showed promising anticancer activity than CP against MCF7 cell line and interaction with calf thymus DNA was studied by fluorescence spectroscopy.[Figure not available: see fulltext.].

1,3-dimethyl-7-substituted-quinazolinyl-2,4-diones, and synthesis method and application thereof

The invention discloses 1,3-dimethyl-7-substituted-quinazolinyl-2,4-diones. The structural general formula of the compounds is disclosed in the specification, wherein R1 is hydrogen or ethyl; and R2 is a benzene ring, benzene ring derivative, heterocyclic ring or aliphatic hydrocarbon. Part of compounds have favorable inhibiting activities for Candida albicans, Aspergillus flavus, Torula histolytica and Aspergillus fumigatus. The compounds have obvious inhibiting activities for chitin synthetase, have favorable antibacterial effects, and can be used for preparing drugs for anti-pathogenic microorganisms.