Name: 2-(4-formylbenzamido)ethyl nitrate
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

4-[(2-Nitroxyethyl)aminocarbonyl]benzaldehyde;

IUPAC Name

2-[(4-formylbenzoyl)amino]ethyl nitrate

Canonical SMILES

C1=CC(=CC=C1C=O)C(=O)NCCO[N+](=O)[O-]

InChI

InChI=1S/C10H10N2O5/c13-7-8-1-3-9(4-2-8)10(14)11-5-6-17-12(15)16/h1-4,7H,5-6H2,(H,11,14)

InChIKey

MEAJXPIXWKHNPY-UHFFFAOYSA-N

Appearance

Soild powder

Shipping

Room temperature

Pharmaceutical Intermediates: 2-(4-formylbenzamido)ethyl nitrate serves as a valuable intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows for modifications that lead to the development of novel therapeutic agents. The ability to functionalize this compound enhances its potential in drug discovery, particularly in the fields of anti-inflammatory and analgesic drugs. By acting as a building block, it contributes to the design of more effective treatments with reduced side effects, thereby playing a crucial role in advancing pharmaceutical research and development.

Agricultural Chemicals: This compound is also utilized in the formulation of agricultural chemicals, particularly as a precursor in the synthesis of plant growth regulators and pesticides. Its chemical properties can be harnessed to create substances that improve crop yield and protect plants from pests and diseases. By promoting healthier plant growth and providing effective pest control solutions, 2-(4-formylbenzamido)ethyl nitrate supports sustainable agricultural practices and contributes to food security, which is increasingly important in the context of global population growth and environmental challenges.

Material Science: In the field of material science, 2-(4-formylbenzamido)ethyl nitrate finds applications in the development of polymers and advanced materials. Its nitrating properties can be leveraged to create modified polymers with enhanced performance characteristics, such as improved thermal stability and chemical resistance. These materials can be used in a variety of applications, including coatings, adhesives, and composites. By enabling the design of materials that meet specific industrial requirements, this compound plays a significant role in innovation and technology advancement within the materials sector.

Explosives: Another critical application of 2-(4-formylbenzamido)ethyl nitrate is in the synthesis of explosives. Its nitrate functional group imparts the compound with the necessary energetic properties that make it suitable for use in explosive formulations. The development of safer and more efficient explosive materials is vital for various industries, including construction, mining, and defense. By contributing to the formulation of advanced explosives that deliver high performance with minimized risk, this compound is essential in enhancing safety and effectiveness in explosive applications.

1. The novel anti-inflammatory agent VA694, endowed with both NO-releasing and COX2-selective inhibiting properties, exhibits NO-mediated positive effects on blood pressure, coronary flow and endothelium in an experimental model of hypertension and endothelial dysfunction

M C Breschi, A Di Capua, G Poce, S Consalvi, A Martelli, L Testai, G Caselli, P Patrignani, M Biava, L Sautebin, V Calderone, C Ghelardini, A Cappelli, M Anzini, A Giordani, L Rovati Pharmacol Res . 2013 Dec;78:1-9. doi: 10.1016/j.phrs.2013.09.008.

Selective cyclooxygenase 2 (COX2) inhibitors (COXIBs) are effective anti-inflammatory and analgesic drugs with improved gastrointestinal (GI) safety compared to nonselective nonsteroidal anti-inflammatory drugs known as traditional (tNSAIDs). However, their use is associated with a cardiovascular (CV) hazard (i.e. increased incidence of thrombotic events and hypertension) due to the inhibition of COX2-dependent vascular prostacyclin. Aiming to design COX2-selective inhibitors with improved CV safety, new NO-releasing COXIBs (NO-COXIBs) have been developed. In these hybrid drugs, the NO-mediated CV effects are expected to compensate for the COXIB-mediated inhibition of prostacyclin. This study evaluates the potential CV beneficial effects of VA694, a promising NO-COXIB, the anti-inflammatory effects of which have been previously characterized in several in vitro and in vivo experimental models. When incubated in hepatic homogenate, VA694 acted as a slow NO-donor. Moreover, it caused NO-mediated relaxant effects in the vascular smooth muscle. The chronic oral administration of VA694 to young spontaneously hypertensive rats (SHRs) significantly slowed down the age-related development of hypertension and was associated with increased plasma levels of nitrates, stable end-metabolites of NO. Furthermore, a significant improvement of coronary flow and a significant reduction of endothelial dysfunction were observed in SHRs submitted to chronic administration of VA694. In conclusion, VA694 is a promising COX2-inhibiting hybrid drug, showing NO releasing properties which may mitigate the CV deleterious effects associated with the COX2-inhibition.

2. Activity of nicorandil, a nicotinamide derivative with a nitrate group, in the experimental model of pain induced by formaldehyde in mice

Raquel R Menezes, Adriana M Godin, Leandro F S Bastos, Isabela C César, Débora P Araújo, Ângelo de Fátima, Renes R Machado, Márcio M Coelho, Wallace C Ferreira, Marcela M G B Dutra, João Gabriel T Seniuk, Darly G Soares, Gerson A Pianetti, Elias B Nascimento Jr Pharmacol Biochem Behav . 2013 May;106:85-90. doi: 10.1016/j.pbb.2013.03.004.

Nicorandil (2-nicotinamide ethyl nitrate), an antianginal drug characterized by the coupling of nicotinamide with a nitric oxide (NO) donor, activates guanylyl cyclase and opens ATP-dependent K(+) channels. In the present study, we investigated the effects induced by per os (p.o.) administration of nicorandil (12.5, 25 or 50 mg/kg) or equimolar doses (corresponding to the highest dose of nicorandil) of N-(2-hydroxyethyl) nicotinamide (NHN), its main metabolite, or nicotinamide in the model of nociceptive response induced by formaldehyde in mice. Nicorandil, but not NHN or nicotinamide, inhibited the second phase of the nociceptive response. This activity was observed when nicorandil was administered between 30 and 120 min before the injection of formaldehyde. Ipsilateral intraplantar injection of nicorandil (125, 250 or 500 μg/paw) did not inhibit the nociceptive response. After p.o. administration of nicorandil (50 mg/kg), peak plasma concentrations of this compound and NHN were observed 0.63 and 4 h later, respectively. Nicotinamide concentrations were not increased after administration of nicorandil. 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one (ODQ; 1 or 2 mg/kg), a guanylyl cyclase inhibitor, partially attenuated the antinociceptive activity of nicorandil. However, this activity was not changed by glibenclamide (30 or 60 mg/kg), an inhibitor of ATP-dependent K(+) channels. In conclusion, we demonstrated the antinociceptive activity of nicorandil in a model of pain that exhibits both a nociceptive and an inflammatory profile. This activity is not mediated by nicotinamide or NHN. The coupling of an NO-donor to nicotinamide results in a compound with an increased potency. The NO-cGMP pathway, but not ATP-dependent K(+) channels, partially mediates the antinociceptive activity of nicorandil.

3. Mutagenicity of new lead compounds to treat sickle cell disease symptoms in a Salmonella/microsome assay

Eliana A Varanda, Lídia Moreira Lima, Chung Man Chin, Jean Leandro dos Santos Int J Mol Sci . 2010 Feb 25;11(2):779-88. doi: 10.3390/ijms11020779.

A series of phthalimide derivatives planned as drugs candidates to treat the symptoms of sickle cell anemia were evaluated in a mutagenicity test using strains of Salmonella typhimurium TA100 and TA102, without and with addition of S9 mixture, with the aim to identify the best structural requirements for a drug candidate without genotoxic activity. The compounds (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl nitrate (1); (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl nitrate (2); 3-(1,3-dioxo-1,3-dihydro-2H-iso-indol-2-yl)benzyl nitrate (3); 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-hydroxy-benzenesulfonamide (4); 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)benzyl nitrate (5) and 2-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]ethyl nitrate (6) presented mutagenic potency ranging between 0-4,803 revertants/micromol. These results allowed us to propose that a methyl spacer linked to a nitrate ester subunit associated to meta aromatic substitution decreases mutagenicity.