20747-39-1

Usage

Uses

Used in Pharmaceutical Synthesis:
SYN-3-NITROBENZALDOXIME is used as a reagent in the synthesis of various pharmaceuticals and organic compounds. Its ability to form oximes, which are important intermediates in organic synthesis, makes it a crucial component in the production of a wide range of compounds.
Used in Organic Chemistry Reactions:
In the field of organic chemistry, SYN-3-NITROBENZALDOXIME is utilized as a reagent for various reactions, particularly in the formation of oximes. Its characteristic properties, due to the presence of the nitro group, contribute to its effectiveness in these reactions.
Used in Medicinal Research:
SYN-3-NITROBENZALDOXIME has been studied for its potential medicinal properties, particularly its ability to inhibit the growth of certain bacteria and fungi. This makes it a valuable compound for research into new antimicrobial agents and treatments.
Used in Chemical Compound Development:
As a derivative of benzaldehyde, SYN-3-NITROBENZALDOXIME is employed in the development of new chemical compounds with potential applications in various industries, including pharmaceuticals, agriculture, and materials science. Its versatility and unique properties make it a valuable asset in the creation of innovative and effective products.

Upstream product

• 79-24-3 Nitroethane 
• 99-61-6 3-nitro-benzaldehyde 
• 108-03-2 1-Nitropropane 
• 619-25-0 3-Nitrobenzyl alcohol 
• 7409-18-9 3-nitrobenzylamine 
• 99-08-1 1-methyl-3-nitrobenzene 
• 3848-31-5 3-nitro-benzaldehyde-((Z)-O-acetyl oxime ) 
• 3717-29-1 E-3-nitrobenzaldoxime 
• 71-43-2 benzene 
• 62-53-3 aniline 
• 932-90-1 syn-benzaldehyde oxime 
• 87-91-2 diethyl (2R,3R)-tartrate 
• 3717-30-4 3-nitrobenzaldoxime 
• 3848-32-6 3-nitro-benzaldehyde-(O-benzoyl oxime ) 

Downstream Products

• 31879-36-4 [5-(3-nitro-phenyl)-[1,2,4]oxadiazol-3-yl]-phenyl-methanone 
• 52629-37-5 O-Trimethylsilyl-p-nitrobenzaldoxim 
• 41542-57-8 N-Hydroxy-3-nitro-thiobenzimidic acid 2-diethylamino-ethyl ester 
• 51003-63-5 3,4-bis(3-nitrophenyl)furoxan 
• 20141-72-4 (C₄H₉)3SnONCHC₆H₄NO₂-3 
• 1449485-50-0 4-(benzo[d][1,3]dioxol-5-yl)-3-(3-nitrophenyl)-4H-spiro[isoxazole-5,3'-pyrido[1,2-a]pyrimidine]-2',4'-dione 
• 1449485-46-4 3-(3-nitrophenyl)-4-phenyl-4H-spiro[isoxazole-5,3'-pyrido[1,2-a]pyrimidine]-2',4'-dione 
• 1449485-48-6 4-(4-chlorophenyl)-3-(3-nitrophenyl)-4H-spiro[isoxazole-5,3'-pyrido[1,2-a]pyrimidine]-2',4'-dione 
• 383894-06-2 ethyl 3-(3-nitrophenyl)isoxazole-5-carboxylate 
• 1488385-43-8 3-(3-nitrophenyl)-5-(2-oxopyrrolidin-1-yl)-4,5-dihydroisoxazole 
• 1488385-70-1 3-(3-nitrophenyl)-5-(pyridin-4-yl)-4,5-dihydoisoxazole 
• 2243-73-4 5-nitrobenzanilide 

Relevant academic research and scientific papers

Synthesis and Antibacterial Evaluation of Benzofuran Based 3,5-Disubstituted Isoxazoles

A series of novel benzofuran-isoxazole 7a–7j hybrid heterocyclic molecules are synthesized. The structures of compounds 7a–7j are assessed by IR, NMR, MASS spectroscopy and elemental analysis. The target compounds 7a–7j are screened for their antibacterial activity and demonstrated excellent to moderate activity against gram-positive and gram-negative bacteria.

Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction

A novel structure of sinomenine isoxazole derivatives is synthesised from sinomenine hydrochloride and aromatic aldehydes and requires six steps. 19 target compounds have been obtained in good yields. The sinomenine hydrochloride transforms to 4-alkynyl sinomenine, which is a key intermediate product to synthesise the target sinomenine isoxazole compounds, after a neutralisation reaction with ammonia and substitution reaction with 3-chloropropyne. Another key intermediate product is 1,3-dipole, which can be obtained from aromatic aldehyde. After treatment with hydroxylamine hydrochloride and then sodium carbonate solution, aromatic aldehyde is converted to aldehyde oxime, which reacts with N-chlorosuccinimide (NCS) to afford aryl hydroximino chloride. 1,3-Dipole is eventually formed in situ while triethylamine (TEA) in DMF is added dropwise. Then 4-alkynyl sinomenine is added to provide the sinomenine isoxazole derivative via 1,3-dipolar cycloaddition reaction as the key step. All the target compounds are characterised by melting point, 1H NMR, 13C NMR, HRMS and FT-IR spectroscopy.

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.

HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids with arylaldehydes: one-pot synthesis of 1-arylisoquinolines

In this paper, a concise, open-vessel synthesis of 1-arylisoquinolines is describedviaHCl-mediated intermolecular cyclocondensation of oxygenated arylacetic acids with arylaldehydes in the presence of NH2OH and alcoholic solvents under mild and one-pot reaction conditions. A plausible mechanism is proposed and discussed herein. In the overall reaction process, only water was generated as the byproduct. Various environmentally friendly reaction conditions are investigated for convenient transformationviathe (4C + 1C + 1N) annulation. This protocol provides a highly effective ring closureviathe formations of one carbon-carbon (C-C) bond, two carbon-nitrogen (C-N) bonds and one carbon-oxygen (C-O) bond.

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.

One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies

Abstract: Regioselective synthesis of some novel 7-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one linked isoxazole hybrids via copper(I) catalyzed one-pot reaction of various aromatic aldehydes with 7-bromo-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one was developed. The structures of the compounds that are synthesized are confirmed by 1H NMR, 13C NMR, and mass spectra. All the hybrids have been tested for their in vitro anticancer activity against four human cancer cell lines, including HeLa, MCF-7, A549, and PC3. Three of the compounds exhibited remarkable anticancer activity compared to standard drug etoposide. Molecular docking studies with EGFR also strengthened the in vitro anticancer activity.

Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis

Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.

1,3-Dipolar Cycloaddition, HPLC Enantioseparation, and Docking Studies of Saccharin/Isoxazole and Saccharin/Isoxazoline Derivatives as Selective Carbonic Anhydrase IX and XII Inhibitors

Two series of saccharin/isoxazole and saccharin/isoxazoline hybrids were synthesized by 1,3-dipolar cycloaddition. The new compounds showed to be endowed with potent and selective inhibitory activity against the cancer-related human carbonic anhydrase (hCA) IX and XII isoforms in the nanomolar range, while no affinity was encountered for off-targets, such as hCA I and II. Successive enantioseparation on a milligram scale of the most representative compounds led to the discovery that (S)-isomers were more potent than their corresponding (R)-enantiomers. Lastly, molecular modeling studies were conducted to define those structural requirements that were responsible for the discrimination among selected human isoforms of carbonic anhydrases. Two nanomolar hCA IX and XII inhibitors were also screened for their selective toxicity against non tumoral primary cells (fibroblasts) and against a breast adenocarcinoma cell line (MCF7) in hypoxic environment. The efficacious combination of these compounds with doxorubicin on MCF7 cells was demonstrated after 72 h of treatment.

Microwave synthesis method of benzaldoxime compounds

The invention discloses a microwave synthesis method of benzaldoxime compounds. The method comprises the following steps: dissolving a substituted benzaldehyde, hydroxylamine hydrochloride and an alkaline compound in an organic solvent, placing the formed solution in a microwave reaction kettle for a reaction, spin-drying the solvent after the reaction is finished, conducting mixed extraction withethyl acetate and water, separating an organic phase, carrying out drying with anhydrous sodium sulfate, and successively performing filtering and desolventizing to obtain a benzaldoxime compound. Based on the structure of the substituted benzaldehyde, the substituted benzaldoxime compound is obtained by reacting the aldehyde with hydroxylamine hydrochloride in the microwave reaction kettle. Themethod is simple in process, convenient to operate, short in reaction time and high in yield, meets the requirement for environment friendliness and improves economic benefits.

A Synergic Activity of Urea/Butyl Imidazolium Ionic Liquid Supported on UiO-66-NH2 Metal–Organic Framework for Synthesis of Oximes

An efficient supported ionic liquid catalyst is designed for condensation reaction of aldehydes and ketones. The Zr-based metal–organic framework (MOF), UiO-66-NH2, was initially functionalized with N,N′-dibutyl imidazolium ionic liquid (UiO-66-NH2-ILBr–), and then urea was attached to the ionic liquid (IL) to form a task-specific IL. Bromide was exchanged with tetrafluoroborate and the catalyst exhibits excellent performance for the synthesis of oximes. The ionic liquid/urea coupling showed a synergistic effect on the efficiency of the reaction. The supported catalyst system was recycled simply by filtration and reused for five times without significant decrease in its activity. The catalyst was characterized with PXRD, FTIR, TGA, XPS, BET, FE-SEM, EDS, elemental mapping and elemental analysis (CHN). Graphic Abstract: MOF/IL/urea catalytic system was used for the synthesis of oximes[Figure not available: see fulltext.].