55860-22-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-N-(2-methoxyphenyl)acetamide is used as a chemical intermediate for the synthesis of various drugs, leveraging its diverse biological activities. Its presence in the acetamide class makes it a valuable component in the development of pharmaceuticals with potential therapeutic applications.

InChI:InChI=1/C14H13ClFNO/c1-9-7-11(14(18)8-15)10(2)17(9)13-6-4-3-5-12(13)16/h3-7H,8H2,1-2H3

Upstream product

• 79-04-9 chloroacetyl chloride 
• 255873-36-0 tert-butyl-N-{4-[allyl(dimethyl)silyl]-2-methoxyphenyl}carbamate 
• 90-04-0 2-methoxy-phenylamine 
• 262433-01-2 (4-bromo-2-methoxyphenyl)carbamic acid tert-butyl ester 
• 59557-91-4 4-bromo-2-methoxyaniline 

Downstream Products

• 38367-24-7 N-(2-methoxy-phenyl)-2-piperidin-1-yl-acetamide 
• 5466-88-6 3,4-dihydro-3-oxo-2H-1,4-benzoxazine 
• 332016-46-3 2-amino-N-(2-methoxyphenyl)ethanamide 
• 50824-49-2 N,N-diethyl-glycine o-anisidide 
• 101862-83-3 S--L-cystein 
• 108086-39-1 N-(2-Methoxy-phenyl)-2-(4-oxo-4H-quinazolin-3-yl)-acetamide 
• 134268-73-8 2-(2'-Hydroxy-biphenyl-2-yloxy)-N-(2-methoxy-phenyl)-acetamide 
• 93-26-5 2-methoxyacetanilide 
• 77775-76-9 N-glycoloyl-o-anisidine 
• 77775-77-0 N-ethoxyacetyl-o-anisidine 
• 79143-75-2 Diethyl-[(2-methoxy-phenylcarbamoyl)-methyl]-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride 
• 17172-64-4 p-formylphenyl o-methoxyphenylcarbamoylmethyl ether 
• 139438-00-9 2-[5-(4-{[1-(1H-Indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(2-methoxy-phenyl)-acetamide 
• 139438-07-6 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-(2-methoxy-phenyl)-acetamide 

Relevant academic research and scientific papers

Synthesis and Anti-inflammatory Activity of Some New 1,2,3-Benzotriazine Derivatives Using 2-(4-Oxo-6-phenylbenzo[d][1,2,3]triazin-3(4H)-yl)acetohydrazide as a Starting Material

In continuation to our search for new heterocyclic system-based anti-inflammatory activity, a series of novel 1,2,3-benzotriazine derivatives were synthesized. The pharmacological screening showed that many of these compounds have good anti-inflammatory activity. The structure assignments of the new synthesized compounds are based on spectroscopic data, and pharmacological properties are reported.

Design, synthesis, docking study and urease inhibitory activity evaluation of novel 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-arylacetamide derivatives

In this paper, novel 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-arylacetamide derivatives (7a–l) are designed, synthesized, and evaluated in vitro for their urease inhibitor activities. The compounds are synthesized efficiently in three steps in high isolated yields from amines, 2-chloroacetyl chloride, hydrazinecarbothioamide, and carbon disulfide. The molecular docking simulation were performed using AutoDock4 by docking all synthesized compound and standard inhibitors into the crystal structure of Jack bean urease. Comparison between the urease inhibitory activity of compounds 7a–l with the IC50 of (2.85–5.83 μM) and thiourea and hydroxyurea as standards inhibitors with the IC50 of (22.00 and 100.00 μM, respectively) proved the high activity of the synthesized compounds against the mentioned enzyme. Docking results were in good agreement with experimental results and indicate that synthesized compounds could interact well with the active site of the urease enzyme and among all; compound 7j shows more favorable interactions with the active site which confirm its great inhibitory activity with IC50 of 2.85 μM. Therefore, compound 7j might be a promising candidate for further evaluation.

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.

A copper-catalyzed synthesis of aryloxy-tethered symmetrical 1,2,3-triazoles as potential antifungal agents targeting 14 α-demethylase

The search for potent therapeutic agents has prompted the design and synthesis of a library of twenty-six aryloxy-tethered and amide-linked symmetrical 1,2,3-triazoles (8a-z) using a copper(i)-catalyzed click chemistry approach. All the synthesized compounds have been screened for theirin vitroantifungal activity against four different fungal strains as well as the enzymatic study for the inhibition of 14 α-demethylase enzyme. The bioactivity results show that most of the synthesized compounds were found to be better antifungal agents as compared to Miconazole. Among them, compound8ashowed the most promising antifungal activity against all the tested fungal strains. Furthermore, the enzymatic study reveals that compounds8iand8oare the most promising inhibitors of the 14 α-demethylase enzyme. In support of these results, the molecular docking study of the synthesized molecules against the sterol 14 α-demethylase (CYP51) could provide the structural basis for the antifungal activity. These compounds have also been analyzed for the ADME properties.

Triazole sulfonamides derivatives and their use in agriculture

The invention provides a novel triazole sulfonamide derivative and application thereof in agriculture. , The invention relates to a triazole sulfonamides derivative as shown in a formula (I) and a preparation method thereof. I In formula (R)1 And R2 Are each independently hydrogen. C1 -6 Alkyl and the like, R3 Document C3 -8 Cycloalkyl, R4 -SO2 - NRa Rb , SO2 - C1 -6 Alkyl group, SO2 - C3 -8 Cycloalkyl, SO2 - C1 -3 Alkylene - C3 -8 Cycloalkyl, SO2 - Rc , C1 -3 Alkylene - C (＝ O) O-C1 -6 Alkyl or - C1 -3 Alkylene - C (＝ O) - NRd Re , Ra , Rb , Rc , Rd And Re Having the meaning of the invention. The compound, the composition containing the compound and/or the preparation provided by the invention has good bactericidal activity and can be used as a bactericide in agriculture.

Design, synthesis and biological evaluation of novel naturally-inspired multifunctional molecules for the management of Alzheimer's disease

In our overall goal to overcome the limitations associated with natural products for the management of Alzheimer's disease and to develop in-vivo active multifunctional cholinergic inhibitors, we embarked on the development of ferulic acid analogs. A systematic SAR study to improve upon the cholinesterase inhibition of ferulic acid with analogs that also had lower logP was carried out. Enzyme inhibition and kinetic studies identified compound 7a as a lead molecule with preferential acetylcholinesterase inhibition (AChE IC50 = 5.74 ± 0.13 μM; BChE IC50 = 14.05 ± 0.10 μM) compared to the parent molecule ferulic acid (% inhibition of AChE and BChE at 20 μM, 15.19 ± 0.59 and 19.73 ± 0.91, respectively). Molecular docking and dynamics studies revealed that 7a fits well into the active sites of AChE and BChE, forming stable and strong interactions with key residues Asp74, Trp286, and Tyr337 in AChE and with Tyr128, Trp231, Leu286, Ala328, Phe329, and Tyr341 in BChE. Compound 7a was found to be an efficacious antioxidant in a DPPH assay (IC50 = 57.35 ± 0.27 μM), and it also was able to chelate iron. Data from atomic force microscopy images demonstrated that 7a was able to modulate aggregation of amyloid β1-42. Upon oral administration, 7a exhibited promising in-vivo activity in the scopolamine-induced AD animal model and was able to improve spatial memory in cognitive deficit mice in the Y-maze model. Analog 7a could effectively reverse the increased levels of AChE and BChE in scopolamine-treated animals and exhibited potent ex-vivo antioxidant properties. These findings suggest that 7a can act as a lead molecule for the development of naturally-inspired multifunctional molecules for the management of Alzheimer's and other neurodegenerative disorders.

Synthesis and evaluation of moxifloxacin derivatives for effects on proliferation and apoptosis of NCI-H1299 cells

Eight novel moxifloxacin (MXF) derivatives 4a-h were synthesized by functional modification of the N-5-Aza ring. Their growth inhibitory activities on human non-small lung cancer cell NCI-H1299 and A549 were evaluated by the MTT colorimetric assay. Based on the half inhibitory concentration (IC50) values, we determined that compounds 4b was the most efficacious derivative (IC50 = 2.56 ± 0.07 μM for NCI-H1299 and IC50 = 13.69 ± 0.70 μM for A549, respectively) that inhibited the proliferation of NCI-H1299 cells. Of these, Compound 4b (1 – cyclopropyl – 6 – fluoro – 8 – methoxy – 4 – oxo – 7 – ((4aS,7aS) – 1 – (2 – oxo – 2 – (p – tolylamino) ethyl) hexahydro – 1H – pyrrolo [3,4-b] pyridine – 6(2H)-yl) – 1,4 – dihydroquinoline – 3-carboxylic acid) showed good potency against the growth of NCI-H1299 cells and also selectivity on HUVEC cells (IC50 > 500 μM). The dose-response relationship of the characteristic morphological changes of NCI-H1299 cells induced by Compound 4b was confirmed by AO/EB fluorescent staining. Furthermore, Compound 4b triggered apoptosis of NCI-H1299 in a concentration-dependent manner and arrested cells in the G0/G1 phase. These data indicate that the N-(p-tolyl)propanamide functionalized N-5-Aza ring of moxifloxacin may be a promising lead compound and candidate for the development of new agents against non-small-cell lung cancer.

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.

Antidiabetic compounds

Compounds for the treatment of hyperglycemia and/or diabetes are provided. The compounds, which inhibit the enzyme dipeptidyl peptidase (DPP-4), are based on the structure where X may be present or absent an may be OH, Ar is an aryl group; and n ranges from 0 to 5.

Discovery of Soft-Drug Topical Tool Modulators of Sphingosine-1-phosphate Receptor 1 (S1PR1)

In order to study the role of S1PRs in inflammatory skin disease, S1PR modulators are dosed orally and topically in animal models of disease. The topical application of S1PR modulators in these models may, however, lead to systemic drug concentrations, wh