35447-75-7

Usage

Uses

Used in Pharmaceutical Industry:
ALPHA-CHLORO-2-NITROBENZALDOXIME is used as an intermediate in the synthesis of pharmaceuticals for its versatile building block properties.
Used in Organic Chemistry:
ALPHA-CHLORO-2-NITROBENZALDOXIME is used as a reagent in organic chemistry reactions due to its nitro and aldoxime functional groups.
Used in Research and Development:
ALPHA-CHLORO-2-NITROBENZALDOXIME is used in the research and development of new drugs, contributing to the discovery and creation of novel pharmaceutical compounds.

InChI:InChI=1/C7H5ClN2O3/c8-7(9-11)5-3-1-2-4-6(5)10(12)13/h1-4,11H/b9-7+

Upstream product

• 4836-00-4 (E)-2-nitrobenzaldehyde oxime 
• 3717-25-7 2-nitrobenzaldehyde oxime 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 22179-83-5 N'-hydroxy-2-nitrobenzimidamide 
• 72590-53-5 3'-(2-nitro-phenyl)-4'H-spiro[adamantane-2,5'-isoxazole] 
• 14442-25-2 3-(2-nitrophenyl)-5-phenyl-1,2-oxazole 
• 128694-18-8 5-Ethoxy-6,6,7,7-tetramethyl-2-(2-nitro-phenyl)-4-oxa-1,3-diaza-bicyclo[3.2.0]hept-2-ene 
• 119931-24-7 3-(2-nitrophenyl)-5-pentylisoxazole 
• 89109-62-6 O-benzoyl-2-nitrobenzohydroximoyl chloride 
• 91956-03-5 ethyl 3-(2-nitrophenyl)-5-methylisoxazole-4-carboxylate 
• 79831-34-8 2-(2-nitrophenyl)-4,5-dihydro-1H-imidazole 
• 103855-76-1 5-ethoxy-3-(2-nitro-phenyl)-isoxazole 
• 325744-47-6 3-(2-nitrophenyl)-5-hydroxymethylisoxazole 
• 957828-76-1 [5-(4-bromophenyl)-3-(2-nitrophenyl)-4,5-dihydroisoxazol-4-yl](phenyl)methanone 
• 957828-77-2 [5-(2,3-dichlorophenyl)-3-(2-nitrophenyl)-4,5-dihydroisoxazol-4-yl](phenyl)methanone 
• 957828-78-3 [5-(2,4-dichlorophenyl)-3-(2-nitrophenyl)-4,5-dihydroisoxazol-4-yl](phenyl)methanone 
• 957828-79-4 [5-(3,4-dichlorophenyl)-3-(2-nitrophenyl)-4,5-dihydroisoxazol-4-yl](phenyl)methanone 

Relevant academic research and scientific papers

Design, synthesis, in vitro and in silico evaluation of new 3-phenyl-4,5-dihydroisoxazole-5-carboxamides active against drug-resistant mycobacterium tuberculosis

A new series of 3-phenyl-4,5-dihydroisoxazole-5-carboxamides were designed, synthesized, and evaluated for their potency against Mtb H37Rv. Designed molecules were synthesized by one-pot cycloaddition reaction in good to excellent yields. Anti-Tubercular evaluation of all synthesized derivatives identified 6k to be highly potent (MIC 1 μg/mL) against Mtb and drug-resistant strains. All potent derivatives were found to be non-toxic when tested against Vero cells. Also, in silico studies were employed to explore the binding patterns of designed compounds to target Mycobacterial membrane protein Large-3. All derivatives exhibited excellent binding patterns with the receptor. The excellent in silico Absorption, Distribution, Metabolism, and Excretion properties and druggability parameters positions these molecules as promising lead candidates for the future development of new drugs to treat drug-resistant Tuberculosis.

Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

Site selective synthesis and anti-inflammatory evaluation of Spiro-isoxazoline stitched adducts of arteannuin B

A library of new spiroisoxazoline analogues of arteannuin B was synthesized through 1, 3-dipolar cycloaddition in stereoselective fashion and consequently screened for anti-inflammatory activity in RAW 264.7 macrophage cells. Three potent analogues (8i, 8 m, and 8n) were found to attenuate the LPS induced release of cytokines IL-6 and TNF-α more potently than the parent molecule. Also, the inhibition of LPS induced nitric oxide production in these cells show moderate to high efficacy. None of the three potent molecules have altered the viability of RAW 264.7 cells following 48 h incubation suggesting that the inhibition of cytokines and nitric oxide production exhibited in the cells was not due to toxicity. In addition, these compounds exhibit an IC50 range of 0.17 μM-1.57 μM and 0.09 μM-0.35 μM for the inhibition of IL-6 release and nitric oxide production respectively. The results disclose potent inhibition of pro-inflammatory mediators which are encouraging and warrant further investigations to develop new therapeutic agents for inflammatory diseases.

Synthesis method of parecoxib sodium isomeric impurities

The invention provides a synthesis method of parecoxib sodium isomeric impurities. Structures of the parecoxib sodium isomeric impurities are shown in formulae I and II in the description. The synthesis method comprises the following steps: the compound as shown in the formula I is subjected to reaction with the compound as shown in formula II or the compound as shown in formula III under the action of alkali, and a compound as shown in formula IV is generated; the corresponding parecoxib sodium isomeric impurities are generated by reduction reaction, diazotization, sulfonylation, amino substitution reaction and acylation reaction; the total reaction yield is higher than 22%, and purity of a target product is higher than 99%.

Simple one-pot synthesis of 5-(chloromethyl)isoxazoles from aldoximes and 2,3-dichloro-1-propene

[Figure not available: see fulltext.] A one-pot synthesis of 3-substituted 5-chloromethylisoxazoles from available starting aldoximes and 2,3-dichloro-1-propene, serving both as a solvent and reagent, is proposed. Excess 2,3-dichloro-1-propene is recovered after the reaction. The synthesis is effective for oximes of both aromatic and aliphatic aldehydes.

Synthesis and biological activity of ethyl 2-(5-methyl-3-arylisoxazole-4-carboxamido)-4-alkylthiazole-5-carboxylate

A series of novel ethyl 2-(5-methyl-3-arylisoxazole-4-carboxamido)-4-alkylthiazole-5-carboxylates I-1-6 were synthesized. The structures of all target compounds were characterized by 1H NMR, 13C NMR, IR,MS and elemental analyses. Their fungicidal and herbicidal activities were evaluated. The results of preliminary bioassays show that the title compounds I-4 possess 20-50% inhibition against most of the tested plants at the dosage of 150 g ai/ha, while the title compounds I-1-5 possess 32-58% inhibition against FusaHum graminearum, Thanatephorus cucumeris, Botrytis cinereapers and Fusarium oxysporum in vitro at the concentration of 100 mg/L.

Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates

A new approach to hetaryl carbamates through a tandem condensation/rearrangement reaction of 2-aminohetarene N-oxides was developed. The developed reaction is suitable for both five- and six-membered heterocycles and proceeds through the condensation of 2

Preparation technology for 3-aryl-4-nitro isoxazole compound

The invention discloses a preparation technology for a 3-aryl-4-nitro isoxazole compound. The preparation technology comprises the following steps: synthesizing a compound shown as formula II through the nucleophilic addition of hydroxylamine hydrochloride and the compound shown as formula I used as the raw material; acquiring the compound shown as formula III through the substitution reaction of the compound shown as formula II and N-chlorosuccinimide; preparing 1-dimethyl amino-2-nitro ethylene through the reaction of N,N-dimethylformamide dimethyl acetal and nitromethane used as the raw material; and acquiring a target product 3-aryl-4-nitro isoxazole compound through the cyclization reaction of the compound shown as formula III and 1-dimethyl amino-2-nitro ethylene. The raw materials in the synthesis route are low in cost and easily acquired, the operation condition is mild and is easily controlled, the product is easily purified and the preparation technology is a new method for synthesizing the 3-aryl-4-nitro isoxazole compound.

A Novel Route to 2-Arylquinolines: Reductive Cleavage of 2′-Nitroaryl-Δ2 -isoxazolines

A novel synthetic route for the synthesis of quinolines starting from Δ 2 -isoxazolines under reductive conditions is reported. The reductive cyclization to quinolines is achieved under both metal and metal-free conditions. The reaction proceeds via an intramolecular N-H?O hydrogen bond intermediate, accelerating the reductive cleavage 1000-fold (DFT calculations) in comparison with non-hydrogen bonded system.

Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions

[3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn(OAc)3 mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 μM, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 μM. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin.