960233-38-9

Upstream product

• 178948-50-0 O²-methyl 1-(4-ethoxycarbonylpiperazin-1-yl)diazen-1-ium-1,2-diolate 
• 178948-50-0 O₂-methyl-1-(4-ethoxycarbonylpiperazin-1-yl)diazen-1-ium-1,2-diolate 

Downstream Products

• 1246199-56-3 O₂-methyl 1-[4-(propargyloxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate 

Relevant academic research and scientific papers

Piperazine as a linker for incorporating the nitric oxide-releasing diazeniumdiolate group into other biomedically relevant functional molecules

Synthetic procedures have been devised to exploit the bifunctional amine piperazine (pip) as a linker capable of attaching the nitric oxide (NO)- releasing diazeniumdiolate functional group [N(O)NO]- to a diverse selection of biomedically useful molecules. One of the amino groups bears the diazeniumdiolate, which may be substituted on oxygen as necessary to control its dissociation to NO, while the other is used to provide a site suitable for covalent bonding to the molecule requiring NO donor capability. N,N'- Disubstituted piperazines of the structure R-pip-N(O)=NOE were prepared either by using the nucleophilic character of the amino group or by converting it into an electrophilic moiety for reaction with nucleophilic centers in the molecules to be derivatized. Examples are reported in which E = CH3 and the R groups are bound to the N'-nitrogen: via amide linkages to the carboxyl groups of the drug ibuprofen and the amino acid derivative N- acetylmethionine; through a urea grouping to the ε-amino group of a protected lysine; via a carbamate linkage to poly(ethylene glycol); and by replacing the NH2 nitrogens of nicotinamide and adenosine. Synthesis of analogues in which E = vinyl has been facilitated by introduction of BrCH2CH2OSO2Cl as a novel, efficient bromoethylating agent. Spontaneous NO releasers in the diazeniumdiolated piperazine series include both a fluorescent anion of half-life 5.5 min in which E = Na and R = dansyl and 'MOM-PIPERAZI/NO' (E = CH3OCH2, R = H), whose half-life for NO release was estimated as 17 days. The latter agent has made possible the conversion of poly(vinyl chloride) and phosphatidylethanolamine to NO-releasing derivatives. This chemistry should allow introduction of diazeniumdiolate groups into a wide variety of natural products, drugs, polymers, and other molecules whose activities could be beneficially combined with the ability to generate NO for biomedical applications.

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.

Biopolymer-bound nitric oxide-releasing compositions, pharmaceutical compositions incorporating same and methods of treating biological disorders using same

A polymeric composition capable of releasing nitric oxide under physiological conditions which includes a biopolymer, such as a peptide, polypeptide, protein, oligonucleotide or nucleic acid, to which is bound a nitric oxide-releasing N2O2?functional group; pharmaceutical compositions comprising the polymeric composition; and methods of treating biological disorders in which dosage with nitric oxide is therapeutic.

Use of nitric oxide-releasing agents for reducing metastasis risk

A method for inhibiting the adherence between cancerous cells and noncancerous structures in a mammal, comprising the administration to the mammal of a nitric oxide-releasing compound containing a nitric oxide-releasing N2 O2- functional group. The compound is capable of releasing an adherence-inhibiting effective amount of nitric oxide to the mammal.