5326-94-3

Usage

Uses

Used in Pharmaceutical Industry:
2-bromo-N-(2-nitrophenyl)acetamide is utilized as a key intermediate in the synthesis of pharmaceuticals for its antimicrobial and antibacterial properties. It aids in the creation of new drugs and pharmaceutical products that can combat various microbial infections.
Used in Organic Synthesis:
In the realm of organic synthesis, 2-bromo-N-(2-nitrophenyl)acetamide is employed as a reagent, facilitating various chemical reactions and experiments. Its unique structure allows it to participate in a range of reactions, making it a versatile tool in research laboratories.
Used in Research Laboratories:
2-bromo-N-(2-nitrophenyl)acetamide is also used in research settings to explore its chemical properties and potential applications. Its presence in experiments can provide insights into new methods of drug development and the understanding of chemical interactions at a molecular level.

InChI:InChI=1/C8H7BrN2O3/c9-5-8(12)10-6-3-1-2-4-7(6)11(13)14/h1-4H,5H2,(H,10,12)

Upstream product

• 88-74-4 2-nitro-aniline 
• 598-21-0 2-Bromoacetyl bromide 
• 22118-09-8 2-bromoacetyl chloride 

Downstream Products

• 493026-69-0 2-(5-methyl-4-p-tolyl-4H-[1,2,4]triazol-3-ylsulfanyl)-N-(2-nitro-phenyl)-acetamide 
• 1194046-54-2 C₃₀H₃₃N₅O₈S 

Relevant academic research and scientific papers

Synthesis and anticoccidial activities of novel N-(2-Aminophenyl)-2- quinazolinone-acetamide hydrochloride

Eight novel N-(2-aminophenyl)-2-quinazolinone-acetamide hydrochloride were synthesized and their structures were identified by 1H NMR, MS and IR spectra. Seven of the new compounds were chosen for anticoccidial activity test and the results showed that N-(2- aminophenyl)-2-(6-methyl-8-bromo quinazolinone) acetamide hydrochloride (3h) exhibited anticoccidial activity against Eimeria tenella in the chicken' diet with a dose of 18 mg/Kg.

Design, synthesis, in vitro antiproliferative evaluation and in silico studies of new VEGFR-2 inhibitors based on 4-piperazinylquinolin-2(1H)-one scaffold

Angiogenesis is essential in the growth of solid tumors which need oxygen and nutrients supply to grow in size. The VEGF/VEGFR-2 signaling pathway plays an important role in tumor angiogenesis. Sorafenib is an FDA approved cancer therapeutic with activity

Facile synthesis, antimicrobial evaluation and molecular docking studies of pyrazole-imidazole-triazole hybrids

A series of eighteen pyrazole-imidazole-triazole hybrid (2-(4-((2-(substituted-1H-pyrazol-1-yl)-4-phenyl-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)-N-(substituted)phenylacetami- de) (6a-6r) are synthesized through click reaction between in situ gener

Synthesis and evaluation of novel pyrazole-imidazole hybrids as antimicrobial candidates

The present study describes a facile and efficient synthesis of 1-(N-arylacetamide)-4-phenyl-2-pyrazolyl-imidazole 7a–7t by reacting 1-(4-phenyl-1H-imidazol-2-yl)-1H-pyrazole (3a)/3,5-dimethyl-1-(4-phenyl-1H-imidazol-2-yl)-1H-pyrazole (3b) with 2-bromo-N-

Synthesis and antidiabetic evaluation of benzimidazole-tethered 1,2,3-triazoles

Some novel benzimidazole-tethered 1,2,3-triazole derivatives (4a–r) were synthesized by a click reaction between 2-substituted 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole and in situ azide. The structures of the synthesized compounds were confirmed by spectroscopic studies (one- and two-dimensional nuclear magnetic resonance, Fourier transform infrared, and high-resolution mass spectra). The synthesized compounds were evaluated for their antidiabetic activity. Compounds 4a–r exhibited a good-to-moderate α-amylase and α-glucosidase inhibitory activity, with IC50 values ranging from 0.0410 to 0.0916 μmol/ml and 0.0146 to 0.0732 μmol/ml, respectively. Compounds 4e, 4g, and 4n were found to be most active. Furthermore, the binding conformation of the most active compounds was ascertained by docking studies.

Amide-Based Cinchona Alkaloids as Phase-Transfer Catalysts: Synthesis and Potential Application

Herein we present a library of simple amide derivatives of Cinchona alkaloids in the form of quaternary ammonium salts. The obtained derivatives can be generated very easily and efficiently from inexpensive and commercially available substrates. We tested this class of alkaloids in the alkylation of glycine derivative, carried out under phase-transfer catalyst conditions. The presented hybrid catalysts offer both high reaction yields (up to 97%) and high enantioselectivities of the obtained product (up to 94% ee).

Synthesis, crystal structure and antimicrobial activity of 2-((2-(4-(1H-1,2,4-triazol-1-yl)phenyl)quinazolin-4-yl)oxy)-N-phenylacetamide derivatives against phytopathogens

Abstract: A total of eighteen 2-((2-(4-(1H-1,2,4-triazol-1-yl)phenyl)quinazolin-4-yl)oxy)-N-phenylacetamide derivatives were designed and synthesized, via hybrid pharmacophore approach. Among these compounds, chemical structure of compound 4a was unambiguously confirmed by means of single-crystal X-ray diffraction analysis. All the compounds were evaluated in vitro for their inhibition activity against several important phytopathogenic bacteria and fungi in agriculture. The obtained results indicated that several compounds demonstrated potent antibacterial activity against Xanthomonas oryzae pv. oryzae (Xoo). For example, compounds 4c, 4g and 4q had EC50 values of 35.0, 36.5 and 32.4 μg/mL toward this bacterium, respectively, around 1.5 times more active than commercial bactericide bismerthiazol (EC50 = 89.8 μg/mL). Additionally, compounds 4j and 4p were found to display comparable antifungal activity against Gloeosporium fructigenum at 50 μg/mL, to commercial fungicide hymexazol. Finally, the relationships between antibacterial activities and molecular structures of this class of compounds were discussed in detail. Graphical abstract: [Figure not available: see fulltext.].

A search for dual action HIV-1 reverse transcriptase, bacterial RNA polymerase inhibitors

Using molecular modeling approach, potential antibacterial agents with triazole core were proposed. A moderate to weak level of antibacterial activity in most of the compounds have been observed, with best minimal inhibitory concentration (MIC) value of 0

Synthesis of novel 1,2,4-triazole derivatives containing the quinazolinylpiperidinyl moiety and: N -(substituted phenyl)acetamide group as efficient bactericides against the phytopathogenic bacterium Xanthomonas oryzae pv. oryzae

A series of novel 1,2,4-triazole derivatives (7a-7p) containing the quinazolinylpiperidinyl moiety and N-(substituted phenyl)acetamide group were designed, synthesized and evaluated for their antimicrobial activities in vitro. These compounds were fully characterized by 1H NMR, 13C NMR, HRMS and IR spectra. Notably, the structure of compound 7p was further confirmed through the single-crystal X-ray diffraction method. The obtained bioassay results indicated that most of these compounds exhibited good to excellent antibacterial activities against the rice bacterial pathogen Xanthomonas oryzae pv. oryzae (Xoo). For example, compounds 7e, 7g, 7n, 7l, 7i, 7k, 7a and 7h had EC50 (half-maximal effective concentration) values of 34.5, 38.3, 39.0, 46.0, 47.5, 54.6, 55.0 and 58.2 μg mL-1 against the bacterium, respectively, which were significantly lower than the control agent Bismerthiazol (85.6 μg mL-1). Additionally, antifungal experiments demonstrated that all the compounds did possess weak inhibition capabilities against three phytopathogenic fungi at 50 μg mL-1, except in the cases of compounds 7e and 7p against the fungus Gibberella zeae. The above experimental results proved that 1,2,4-triazole derivatives bearing both a quinazolinylpiperidinyl fragment and N-(substituted phenyl)acetamide unit are promising candidates for the development of new agricultural bactericides against the pathogenic bacterium Xoo, deserving further investigation in the future.

Searching for novel scaffold of triazole non-nucleoside inhibitors of HIV-1 reverse transcriptase

Azoles are a promising class of the new generation of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). From thousands of reported compounds, many possess the same basic structure of an aryl substituted azole ring linked by a thioglycolamide chain with another aromatic ring. In order to find novel extensions for this basic scaffold, we explored the 5-position substitution pattern of triazole NNRTIs using molecular docking followed by the synthesis of selected compounds. We found that heterocyclic substituents in the 5-position of the triazole ring are detrimental to the inhibitory activity of compounds with four-membered thioglycolamide linker and this substitution seems to be viable only for compounds with shorter two-membered linker. Promising compound, N-(4-carboxy-2-chlorophenyl)-2-((4-benzyl-5-methyl-4H-1,2,4-triazol-3-yl)sulfanyl)acetamide, with potent inhibitory activity and acceptable aqueous solubility has been identified in this study that could serve as lead scaffold for the development of novel water-soluble salts of triazole NNRTIs.