2879-79-0

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-METHYL-5-NITROPHENYL)ACETAMIDE is used as a pharmaceutical intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its presence of nitro and amide functional groups contributes to its utility in drug development.
Used in Medicinal Chemistry Research:
N-(2-METHYL-5-NITROPHENYL)ACETAMIDE is utilized in medicinal chemistry research due to its potential biological activities, including anti-inflammatory and analgesic properties. These properties make it a promising candidate for the development of new therapeutic agents.
However, it is important to note that as with any chemical, caution should be taken when handling N-(2-methyl-5-nitrophenyl)acetamide, as it may have potential health and environmental hazards.

InChI:InChI=1/C9H10N2O3/c1-6-3-4-8(11(13)14)5-9(6)10-7(2)12/h3-5H,1-2H3,(H,10,12)

Upstream product

• 120-66-1 N-(2-methylphenyl)acetamide 
• 108-24-7 acetic anhydride 
• 99-55-8 2-methyl-5-nitroaniline 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 95-53-4 o-toluidine 
• 75-36-5 acetyl chloride 

Downstream Products

• 3484-28-4 acetic acid-(6-methyl-2,3-dinitro-anilide) 
• 70343-12-3 2-acetamido-4,5-dinitrotoluene 
• 5434-30-0 N-(5-amino-2-methylphenyl)acetamide 
• 3484-29-5 2,3-dinitro-6-methylaniline 
• 70343-04-3 3,4-dinitro-6-methylaniline 
• 951-97-3 2-acetamido-4-nitrobenzoic acid 
• 91573-24-9 2-methyl-5-nitro-diacetanilide 
• 286461-72-1 4-Acetylamino-5-methyl-2-nitro-benzenesulfonyl chloride 
• 651733-07-2 2-acetamido-4-nitrobenzyl bromide 
• 78468-34-5 (2-Amino-4-nitrophenyl)methan-1-ol 
• 651733-13-0 2-acetamido-4-nitrobenzyl alcohol 
• 1025993-00-3 2-(4-Acetylamino-5-methyl-2-nitro-benzenesulfonylamino)-4-methyl-thiazole-5-carboxylic acid ethyl ester 
• 2836-00-2 3-amino-4-methylphenol 
• 55204-24-5 ethyl 2-amino-4-nitrobenzoate 

Relevant academic research and scientific papers

Nitrobenzocyclophosphamides as potential prodrugs for bioreductive activation: Synthesis, stability, enzymatic reduction, and antiproliferative activity in cell culture

In efforts to obtain potential anticancer prodrugs for gene-directed enzyme prodrug therapy using Eschericia coli nitroreductase, a series of four benzocyclophosphamide analogues were designed and synthesized incorporating a strategically placed nitro group in a position para to the benzylic carbon for reductive activation. All four analogues were found to be stable in phosphate buffer at pH 7.4 and 37 °C and were good substrates of E. coli nitroreductase with half lives between 7 and 24 min at pH 7.0 and 37 °C. However, only two analogues 6a and 6c, both with a benzylic oxygen in the phosphorinane ring para to the nitro group, showed a modest 33-36-fold enhanced cytotoxicity in E. coli nitroreductase-expressing cells. These results suggest that good substrate activity and the para benzylic oxygen are required for activation by E. coli nitroreductase. Compounds 6a and 6c represent a new structure type for reductive activation and a lead for further modification in the development of better analogues with improved selective toxicity to be used in gene-directed enzyme prodrug therapy.

INHIBITORS OF NECROPTOSIS

The invention relates to novel heterocyclic compounds of Formula (I) which inhibit necroptosis and methods for their use. The compounds may be useful in the treatment of conditions associated with deregulated necroptosis.

Functionalization of quinazolin-4-ones part 1: Synthesis of novel 7-substituted-2-thioxo quinazolin-4-ones from 4-substituted-2-aminobenzoic acids and PPh3(SCN)2

4-(Nitro, amino, acetylamino)-2-aminobenzoic acid were allowed to react with PPh3(SCN)2 and gave the crossholding 7-nitro, 7-acetylamino- and 7-amino-2-thioxo quinazolin-4-ones respectively. The nature of the substituent at position 4 of the 2-aminobenzoic acids has significant influence on the outcome of the cyclisation reaction with PPh 3(SCN)2. Similarly, the nature of the substituent at position 7 of the 2-substituted quinazolin-4-ones significantly affected the ease with which alkylation reactions could be performed. The alkylation selectivity of the 7- substiuted-2-thioxo quinazolin-4-ones was found to depend on the nature of the alkyl halide and the nature of the substituent at position 2.

A new ferrocene-based bulky pyridine as an efficient reusable homogeneous catalyst

An effective approach to reusing a homogeneous catalyst has been demonstrated. A ferrocene-based bulky pyridine has been synthesized and utilized as a homogeneous catalyst for the synthesis of benzoylfumarates as well as for acetylation. After the reaction, the catalyst was separated by simple precipitation and reused without appreciable loss of activity. The Royal Society of Chemistry 2013.

3 -CYANO- 5 -ARYLAMINO-7 -CYCLOALKYLAMINOPYRROLO [1, 5 -A] PYRIMIDINE DERIVATIVES AND THEIR USE AS ANTITUMOR AGENTS

The invention relates to chemical compounds of Formula (I): or a salt thereof. In some embodiments, the invention relates to inhibitors of CK2. In still further embodiments, the invention relates to pharmaceutical compositions comprising compounds disclosed herein and their use in the prevention and treatment of CK2-related conditions and diseases, e.g., cancer.

New diarylureas and diarylamides possessing acet(benz)amidophenyl scaffold: Design, synthesis, and antiproliferative activity against melanoma cell line

A series of new diarylurea and diarylamide derivatives possessing acet(benz)amidophenyl scaffold was synthesized. Their in vitro antiproliferative activity was tested against A375P human melanoma cell line. Compounds 1c,d and 2c,d showed the highest potencies with IC50 values in sub-micromolar scale. In addition, compounds 1b,e,l and 2e,l were more potent than Sorafenib but with IC50 values in micromolar range. Moreover, compound 2c was equipotent to Vemurafenib, and 2d showed higher potency than Vemurafenib against A375P. Molar refractometry calculation and ADME profiling of the highest potent four derivatives 1c,d and 2c,d are also reported.

Nitroaryl phosphoramide compositions and methods for targeting and inhibiting undesirable cell growth or proliferation

The present invention relates to nitroaryl-substituted phosphoramide prodrug compounds and methods of producing the same for use in targeting and inhibiting undesirable cell growth or proliferation.

Nitroaryl Phosphoramides as Novel Prodrugs for E. coli Nitroreductase Activation in Enzyme Prodrug Therapy

Cyclic and acyclic nitroaryl phosphoramide mustard analogues were activated by E. coli nitroreductase, an enzyme explored in GDEPT. The more active acyclic 4-nitrobenzyl phosphoramide mustard (7) showed 167 500x selective cytotoxicity toward nitroreductase-expressing V79 cells with an IC50 as low as 0.4 nM. This is about 100x more active and 27x more selective than CB1954 (1). The superior activity was attributed to its better substrate activity (kcat/Km 19x better than 1) and/or excellent cytotoxicity of phosphoramide mustard released.

Effect of substituents in the formation of diacetanilides

A number of diacetanilides, including some which have not been reported so far, have been synthesized from the corresponding monoacetyl derivatives and characterized by spectral and elemental analyses.A tlc/fid method for the quantitative estimation of the relative amounts of mono- and diacetyl derivatives has been standardized.Linear correlation of the extent of diacetylation with Hammett ?-values of substituents and basicity constants of monoacetyl derivatives has been established.A plausible mechanism for the diacetylation reaction based on experimental observations has been suggested.An explanation for the anomalous behaviour of acetanilides containing electron-withdrawing substituents in the ortho-position has been put forth.