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Home > Nitro Compounds > 287118-97-2
287118-97-2 | Benzoic acid, 2-(acetyloxy)-, 4-[(nitrooxy)methyl]phenyl ester
CAS No: 287118-97-2 Catalog No: AG002W7O MDL No:
Product Description
Catalog Number:
AG002W7O
Chemical Name:
Benzoic acid, 2-(acetyloxy)-, 4-[(nitrooxy)methyl]phenyl ester
CAS Number:
287118-97-2
Molecular Formula:
C16H13NO7
Molecular Weight:
331.2769
IUPAC Name:
[4-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate
InChI:
InChI=1S/C16H13NO7/c1-11(18)23-15-5-3-2-4-14(15)16(19)24-13-8-6-12(7-9-13)10-22-17(20)21/h2-9H,10H2,1H3
InChI Key:
CTHNKWFUDCMLIQ-UHFFFAOYSA-N
SMILES:
[O-][N+](=O)OCc1ccc(cc1)OC(=O)c1ccccc1OC(=O)C
Properties
Complexity:
454
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
331.069g/mol
Formal Charge:
0
Heavy Atom Count:
24
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
331.28g/mol
Monoisotopic Mass:
331.069g/mol
Rotatable Bond Count:
7
Topological Polar Surface Area:
108A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.9
Literature
| Title | Journal |
|---|---|
| Quinone-induced activation of Keap1/Nrf2 signaling by aspirin prodrugs masquerading as nitric oxide. | Chemical research in toxicology 20121217 |
| Synthesis and biological activity of acetyl-protected hydroxybenzyl diethyl phosphates (EHBP) as potential chemotherapeutic agents. | Bioorganic & medicinal chemistry letters 20111201 |
| New microtubule polymerization inhibitors comprising a nitrooxymethylphenyl group. | Bioorganic & medicinal chemistry 20110701 |
| Nitric oxide-donating acetylsalicylic acid induces apoptosis in chronic lymphocytic leukemia cells and shows strong antitumor efficacy in vivo. | Clinical cancer research : an official journal of the American Association for Cancer Research 20110115 |
| Modulation of stress genes expression profile by nitric oxide-releasing aspirin in Jurkat T leukemia cells. | Biochemical pharmacology 20100615 |
| NCX 4040, a nitric oxide-donating aspirin, exerts anti-inflammatory effects through inhibition of I kappa B-alpha degradation in human monocytes. | Journal of immunology (Baltimore, Md. : 1950) 20100215 |
| Nitro-aspirin inhibits MCF-7 breast cancer cell growth: effects on COX-2 expression and Wnt/beta-catenin/TCF-4 signaling. | Biochemical pharmacology 20091115 |
| Modulation of carcinogen metabolism by nitric oxide-aspirin 2 is associated with suppression of DNA damage and DNA adduct formation. | The Journal of biological chemistry 20090814 |
| Comparative effects of aspirin and NO-releasing aspirins on differentiation, maturation and function of human monocyte-derived dendritic cells in vitro. | International immunopharmacology 20090701 |
| The thioredoxin system mediates redox-induced cell death in human colon cancer cells: implications for the mechanism of action of anticancer agents. | Cancer research 20081015 |
| NCX 4040, an NO-donating acetylsalicylic acid derivative: efficacy and mechanisms of action in cancer cells. | Nitric oxide : biology and chemistry 20080901 |
| Nitrates and NO-NSAIDs in cancer chemoprevention and therapy: in vitro evidence querying the NO donor functionality. | Nitric oxide : biology and chemistry 20080901 |
| A comparison of the effectiveness of selected non-steroidal anti-inflammatory drugs and their derivatives against cancer cells in vitro. | Cancer chemotherapy and pharmacology 20080201 |
| NCX-4040, a nitric oxide-releasing aspirin, sensitizes drug-resistant human ovarian xenograft tumors to cisplatin by depletion of cellular thiols. | Journal of translational medicine 20080101 |
| Quinone formation as a chemoprevention strategy for hybrid drugs: balancing cytotoxicity and cytoprotection. | Chemical research in toxicology 20071201 |
| Chemical insights in the concept of hybrid drugs: the antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin. | Journal of medicinal chemistry 20070517 |
| Study of molecular mechanisms of pro-apoptotic activity of NCX 4040, a novel nitric oxide-releasing aspirin, in colon cancer cell lines. | Journal of translational medicine 20070101 |
| Molecular characterization of cytotoxic and resistance mechanisms induced by NCX 4040, a novel NO-NSAID, in pancreatic cancer cell lines. | Apoptosis : an international journal on programmed cell death 20060801 |
| Efficacy of a nitric oxide-releasing nonsteroidal anti-inflammatory drug and cytotoxic drugs in human colon cancer cell lines in vitro and xenografts. | Molecular cancer therapeutics 20060401 |
| Nitric oxide-donating aspirin induces apoptosis in human colon cancer cells through induction of oxidative stress. | Proceedings of the National Academy of Sciences of the United States of America 20051122 |
| Pro-apoptotic effect of a nitric oxide-donating NSAID, NCX 4040, on bladder carcinoma cells. | Apoptosis : an international journal on programmed cell death 20051001 |
| Expression and functional activity of phosphodiesterase type 5 in human and rabbit vas deferens. | Molecular human reproduction 20050201 |
| NO-donating aspirin inhibits the growth of leukemic Jurkat cells and modulates beta-catenin expression. | Biochemical and biophysical research communications 20050107 |
| Nitroaspirins and morpholinosydnonimine but not aspirin inhibit the formation of superoxide and the expression of gp91phox induced by endotoxin and cytokines in pig pulmonary artery vascular smooth muscle cells and endothelial cells. | Circulation 20040831 |
| Nitric oxide donating nonsteroidal anti-inflammatory drugs induce apoptosis in human prostate cancer cell systems and human prostatic stroma via caspase-3. | The Journal of urology 20040701 |
| Nitric oxide-donating aspirin inhibits beta-catenin/T cell factor (TCF) signaling in SW480 colon cancer cells by disrupting the nuclear beta-catenin-TCF association. | Proceedings of the National Academy of Sciences of the United States of America 20031028 |
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