138475-09-9

Usage

Chemical Properties

White to yellow powder

InChI:InChI=1/C4H10N3O2/c1-3-6(4-2)7(9)5-8/h3-4H2,1-2H3/q-1

Upstream product

• 109-89-7 diethylamine 

Downstream Products

• 109-89-7 diethylamine 
• 1412945-43-7 C₂₃H₂₉N₉O₇S 
• 1433997-58-0 C₂₃H₂₉N₉O₇S 
• 1402070-26-1 C₂₈H₃₃N₅O₇S 
• 1412945-39-1 C₂₆H₃₁N₅O₇S₂ 
• 1433997-57-9 C₂₆H₃₁N₅O₇S₂ 
• 55-18-5 N-Nitrosodiethylamine 
• 1093078-06-8 O₂-(2,4-dinitro-5-fluorophenyl) 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate 
• 1093077-91-8 1-[1-(N,N-dimethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-[1-(N,N-diethylamino)diazen-1-ium-1,2-diol-2-ato]benzene 
• 694-54-2 tetrahydro-2H-2-pyranol 
• 1037206-77-1 O₂-tetrahydropyran-2-yl 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate 
• 1070883-64-5 O⁽²⁾-((5-nitro-2-(tetrahydropyran-2-yloxy)phenyl)methyl)-1-( N,N-diethylamino)diazen-1-ium-1,2-diolate 
• 112753-64-7 1-n-Propoxy-2-oxo-3,3-diethyl-1-triazene 
• 143706-24-5 1-((2-Hydroxycyclohexyl)oxy)-2-oxo-3,3-diethyl-1-triazene 

Relevant academic research and scientific papers

Synthesis of 1-[(nitroxyalkoxy)methoxy]-1-triazene 2-oxides, new hybrid nitrogen monoxide donors

1-[(Nitroxyalkoxy)methoxy]-3,3-dialkyl-1-triazene 2-oxides were obtained by the reaction of 3,3-dialkyl-1-hydroxy-1-triazene 2-oxide sodium salts with β- or γ-nitroxyalcohol chloromethyl ethers or by the reaction of 3,3-dialkyl-1-(bromoalkoxymethoxy)-1-triazene 2-oxides with silver nitrate. These compounds can be of interest as new hybrid NO donors in living organisms.

Synthesis and Evaluation of O 2-Derived Diazeniumdiolates Activatable via Bioorthogonal Chemistry Reactions in Living Cells

A class of O2-alkyl derived diazeniumdiolates 3a-f and 4a-c were designed and synthesized as new bioorthogonal NO precursors, which can be effectively uncaged in the presence of a palladium catalyst via bioorthogonal bond cleavage reactions to generate NO in living cancer cells, eliciting potent antiproliferative activity.

Synthesis of methylene-bis(1-oxy-3,3-dialkyl-1-triazene 2-oxides) and their analogs

Synthetic procedures towards methylene-bis(1-oxy-3,3-dialkyl-1-triazene 2-oxides), the first representatives of a new class of promising exogenous nitric oxide (NO) donors, which can release NO in living organisms, were developed. Synthesis involves the reactions of salts of 1-hydroxy-3,3-dialkyl-1-triazene 2-oxides with either dibromomethane or 1-chloromethoxy-3,3-dialkyl-1-triazene 2-oxides.

O 2-3-Aminopropyl diazeniumdiolates suppress the progression of highly metastatic triple-negative breast cancer by inhibition of microvesicle formation via nitric oxide-based epigenetic regulation

Currently, there is no effective therapy for the treatment of highly metastatic triple-negative breast cancer (TNBC). Microvesicle (MV) formation is crucial for the metastasis of TNBC. Here we report a novel strategy to inhibit the generation of MVs for the intervention of TNBC. O2-3-Aminopropyl diazeniumdiolates 3a-f are designed and synthesized, which can be activated by lysyloxidase over-expressed in TNBC cells. The most active compound 3f is able to selectively release high levels of NO in TNBC cells, inhibit the cell proliferation, and reduce the adhesion, invasion and migration of TNBC cells in vitro. Furthermore, 3f significantly suppresses the growth and metastasis of implanted TNBC in vivo through attenuating MV formation by an epigenetic modification of miR-203/RAB22A expression in an NO-dependent manner, providing the first evidence of NO donor(s) acting as epigenetic modulators to fight highly metastatic TNBC.

Design, synthesis and cytotoxic evaluation of nitric oxide-releasing derivatives of isosteviol

Twenty-six novel isosteviol derivatives coupled with two types of nitric oxide (NO) donors (furoxans and NONOates) were synthesized and screened for cytotoxic activities against four human cancer cell lines with sunitinib as the positive control. The results showed that seven furoxan-based derivatives (8a, 8b, 8c, 8d, 8e, 9e, and 9f) exhibited desirable cytotoxic activities, while NONOate-based derivatives displayed poor potency because of unstability. Compared with sunitinib, compounds 8a and 8e were more active on all tested cell lines, especially in HCT116 (8a, IC50?=?0.48?±?0.02?μm; 8e, IC50?=?0.94?±?0.01?μm); compounds 8b and 8d were more potent on HCT116 (IC50?=?3.39?±?0.06 and 3.29?±?0.03?μm), HepG2 (IC50?=?1.05?±?0.03 and 5.37?±?0.08?μm), and SW620 (IC50?=?1.33?±?0.02 and 4.11?±?0.05?μm) cell lines, and 8c exhibited higher activities on HepG2 cells with an IC50?=?4.76?±?0.14?μm. NO-releasing experiment of compounds 8a–e, 17a, 18a, 19a, and 21a reminded us that NO-releasing amount of this series of isosteviol derivatives positively correlates with their cytotoxic activities.

COMPOSITIONS AND METHODS OF DIAZENIUMDIOLATE-BASED PRODRUGS FOR TREATING CANCER

The present disclosure provides methods utilizing the diazeniumdiolate-based prodrugs for the treatment of cancer via various mechanisms and procedures. The disclosure also provides kits comprising the diazeniumdiolate-based prodrugs. Despite the fact tha

ALLOSTERIC HEMOGLOBIN MODIFIERS WITH NITRIC OXIDE RELEASING MOIETY

Allosteric hemoglobin (Hb) modifiers of hemoglobin which contain nitric oxide (NO) moieties allowing for the release of NO in vivo. The compounds retain the oxygen delivery capability of the allosteric hemoglobin modifier to bind Hb and enhance Hb's abili

Synthesis and properties of 2-hydroxyethyl derivatives of methylene-bis(1-oxy-3, 3-dialkyl-1-triazene 2-oxides)

Synthetic approach to 2-hydroxyethyl derivatives of methylene-bis(1-oxy-3, 3-dialkyl-1triazene 2-oxides), promising NO donors, which can release NO in living organisms was developed. Some transformations of the hydroxyethyl moiety of the synthesized compounds were studied.

DUAL ACTION NITRIC OXIDE DONORS AND THEIR USE AS ANTIMICROBIAL AGENTS

The present invention relates generally to conjugates comprising a nitric oxide donor and an acyl homoserine lactone, fimbrolide, fimbrolide derivative, dihydropyrrolone or indole, and to the use of such conjugates as antimicrobial agents.

Hybrid molecule from O2-(2,4-dinitrophenyl)diazeniumdiolate and oleanolic acid: A glutathione S-transferase π-activated nitric oxide prodrug with selective anti-human hepatocellular carcinoma activity and improved stability

A series of hybrids from O2-(2,4-dinitrophenyl)diazeniumdiolate and oleanolic acid (OA) were designed, synthesized, and biologically evaluated as novel nitric oxide (NO)-releasing prodrugs that could be activated by glutathione S-transferase π (GSTπ) overexpressed in a number of cancer cells. It was discovered that the most active compound, 21, released high levels of NO selectively in HCC cells but not in the normal cells and exhibited potent antiproliferative activity in vitro as well as remarkable tumor-retarding effects in vivo. Compared with the reported GSTπ-activated prodrugs JS-K and PABA/NO, 21 exhibited remarkably improved stability in the absence of GSTπ. Importantly, the decomposition of 21 occurred in the presence of GSTπ and was much more effective than in glutathione S-transferase α. Additionally, 21 induced apoptosis in HepG2 cells by arresting the cell cycle at the G2/M phase, activating both the mitochondrion-mediated pathway and the MAPK pathway and enhancing the intracellular production of ROS.