2574-03-0

Basic information

• Product Name: [(4-nitrophenyl)methylidyne]azane oxide
• CAS NO: 2574-03-0
• Molecular Formula: C₇H₄N₂O₃
• Molecular Weight: 164.1183
• Mol File: 2574-03-0.mol

Chemical Properties

• Density: 1.32g/cm³
• Refractive Index: 1.589
• CAS DataBase Reference: [(4-nitrophenyl)methylidyne]azane oxide(CAS DataBase Reference)
• NIST Chemistry Reference: [(4-nitrophenyl)methylidyne]azane oxide(2574-03-0)
• EPA Substance Registry System: [(4-nitrophenyl)methylidyne]azane oxide(2574-03-0)

Safety Data

• Hazardous Substances Data: 2574-03-0(Hazardous Substances Data)

Upstream product

• 1011-84-3 4-nitrobenzohydroximoyl chloride 
• 1129-37-9 4-nitrobenzaldehyde oxime 
• 555-16-8 4-nitrobenzaldehdye 
• 122-04-3 4-nitro-benzoyl chloride 
• 58402-81-6 (Z)-4-nitrobenzohydroximoyl chloride 

Downstream Products

• 32527-68-7 4,6-dimethoxy-3-(4-nitro-phenyl)-3a,4,6,6a-tetrahydro-furo[3,4-d]isoxazole 
• 10221-34-8 2-methyl-5-[3-(4-nitro-phenyl)-[1,2,4]oxadiazol-5-yl]-2H-tetrazole 
• 30377-02-7 (Ξ)-3-(4-nitro-phenyl)-5-((4R,4'R)-2,2,2',2'-tetramethyl-(4rH)-tetrahydro-[4,4']bi[1,3]dioxolyl-5c-yl)-4,5-dihydro-isoxazole 
• 32527-70-1 4ξ,6-dimethoxy-3-(4-nitro-phenyl)-(3ar,6ac)-3a,4,6,6a-tetrahydro-furo[3,4-d]isoxazole-6ξ-carboxylic acid methyl ester 
• 30361-13-8 (4S)-O³-benzyl-O¹,O²-isopropylidene-4-[(Ξ)-3-(4-nitro-phenyl)-4,5-dihydro-isoxazol-5-yl]-β-L-threofuranose 
• 38708-01-9 5-nitromethyl-3-(4-nitro-phenyl)-4,5-dihydro-isoxazole 
• 39726-24-4 O¹,O²;O⁵,O⁶-diisopropylidene-3'-(4-nitro-phenyl)-4'H-spiro[α-D-3-deoxy-glucofuranose-3,5'-isoxazole] 
• 61428-19-1 5-methyl-5-nitromethyl-3-(4-nitro-phenyl)-4,5-dihydro-isoxazole 
• 71471-70-0 [5-((3aR)-6c-methoxy-2,2-dimethyl-(3ar,6ac)-tetrahydro-furo[2,3-d][1,3]dioxol-5c-yl)-3-(4-nitro-phenyl)-isoxazol-4-yl]-phosphonic acid diethyl ester 
• 71471-73-3 [5-((3aR)-6c-methoxy-2,2-dimethyl-(3ar,6ac)-tetrahydro-furo[3,4-d][1,3]dioxol-4c-yl)-3-(4-nitro-phenyl)-isoxazol-4-yl]-phosphonic acid diethyl ester 
• 34253-27-5 C₁₁H₁₅N₂O₅P 
• 50336-46-4 1,2,3,4,5,6-hexamethyl-9-(4-nitro-phenyl)-7-oxa-8-aza-tricyclo[4.3.0.0^2,5]nona-3,8-diene 
• 50438-70-5 5-(4-methoxy-phenethyloxy)-3-(4-nitro-phenyl)-5-phenyl-[1,4,2]oxathiazole 
• 71637-72-4 3a,5-diethyl-3-(4-nitro-phenyl)-6,6a-diphenyl-(3ar,6ac)-3a,6a-dihydro-cyclopenta[d]isoxazol-4-one 

Relevant articles and documents

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.

One-pot Synthesis of Some Novel Xanthine Derived Isoxazoles as Potent Antibacterial Agents

In search of better antibacterial agents, a series of novel xanthine derived 3,5-disubstituted isoxazole derivatives were synthesized (3a-3j) in one-pot using 8-chloro-1,3-dimethyl-7-(prop-2-yn-1-yl)-1H-purine-2,6(3H,7H)-dione and aromatic aldehydes and f

One-pot synthesis of novel ether-linked diisoxazole derivatives via sequential O-propargylation and 1,3-dipolar cycloaddition from 2-bromohomoallylic alcohols

A simple and efficient, one-pot approach for the synthesis of ether-linked diisoxazole derivatives has been developed through sequential reactions, which includes O-propargylation of 2-bromohomoallylic alcohols with propargyl bromide in the presence of so

1,3-Dipolar cycloaddition reactions of acyl phosphonates with nitrile oxides: synthesis of phosphonate-containing dioxazole derivatives

New phosphonate-containing five-membered heterocyclic dioxazole derivatives are synthesized via 1,3-dipolar cycloaddition reactions of nitrile oxides used as dipole with acyl phosphonates under basic conditions. Herein, acyl phosphonates take part in the

One Pot Synthesis and Antitumor Activity of Isoxazole-Pyrimido[4,5-c]isoquinolines

Abstract: A number of new isoxazole coupled pyrimido[4,5-c]isoquinolines has been synthesized in good to excellent yields by the one pot method. The Cu(I)-catalyzed cycloaddition reaction between the terminal alkyne 4 and various aldehydes has led to nitr

Cu(I)-Catalysis of One-Pot Synthesis of Some Novel Regioselective Isoxazole-Benzimidazole Hybrids and Their In Vitro Anti-Cancer Evaluation

Regioselective synthesis of some novel isoxazole-benzimidazole hybrids in high yields via Cu(I)-catalyzed tandem one-pot reaction of aromatic aldehydes with 1-prop-2-ynylbenzimidazole is developed. Structures of the synthesized compounds are confirmed by

An efficient protocol for the synthesis of six-membered N, O-heterocycles via a 1,3-dipolar (3+3) cycloaddition between nitrile oxide and α-diazo esters

In this manuscript, we are reporting an efficient protocol for the construction of highly functionalized N, O-heterocyclic derivatives such as 1,2,4-oxadiazine and 1,4,2-dioxazine-6-carboxylate derivatives via a 1,3-dipolar (3 + 3) cycloaddition between nitrile oxide and unprotected α-diazo esters in the presence of 2 mol% Cu(OTf)2 catalyst. The expected N, O-heterocycles were obtained in excellent yields. These N, O-heterocycles are known to exhibit insecticidal and acaricidal properties.

Synthesis, antimalarial activity, and target binding of dibenzazepine-tethered isoxazolines

Malaria, a complex and deadly parasitic infectious disease, is a huge public health problem in many endemic countries around the globe. The prevailing extensive resistance of malaria parasites to traditional drugs and emergence of resistance to the currently used frontline artemisinin-based chemotherapy calls for the development of new drugs. Towards this objective and since compounds containing the dibenzazepine moiety are effective in treating both gametocyte and asexual stage malaria parasites, including multi drug resistant parasites, a library of dibenzazepine tethered 3,5-disubstituted isoxazolines was synthesised via 1,3-dipolar cycloaddition reaction. An additional diversified group of dibenzazepine derivatives were accessed by Suzuki coupling of one of the above dibenzazepine derivatives with various organoboronic acids. All compounds were structurally characterized and were evaluated for their antimalarial activity. They exhibited good to excellent inhibitory activity against the growth of drug-sensitive Plasmodium falciparum 3D7 strain with IC50 values ranging from 0.2 to 7.7 μM. About 50% of the compounds were either minimally or not toxic to human cell lines. Five of the compounds (6j, 6k, 8c, 8k and 8l) that highly inhibited the parasite growth were further assessed for antimalarial activity using an additional chloroquine-sensitive (D6) and two chloroquine-resistant (W2 and 7G8) P. falciparum strains. These compounds were effective against all four strains (3D7, D6, W2 and 7G8), exhibiting IC50 values of 0.1 to 1.75 μM. The dibenzazepines were identified to target the metalloamino-peptidase of parasites. Molecular docking and dynamics simulation studies were performed to understand the binding mode and binding strengths of the selected compounds with the enzyme. In agreement with their excellent antimalarial activity, the data suggested that the compounds can strongly bind to the active site of the enzyme.

A facile one-pot synthesis of 3,5-disubstituted isoxazole derivatives using hydroxy (tosyloxy) iodobenzene

Hydroxy (tosyloxy) iodobenzene (HTIB), a hypervalent iodine reagent, has been extensively used for oxidative transformations. We have developed a one-pot synthesis wherein aldoximes when reacted with alkynes in the presence of HTIB result in the direct formation of isoxazoles. This simple and straightforward reaction allows for ease of purification while leading to the formation of high purity 3,5-disubstituted isoxazoles in moderate yields.