NO-aspirin

Base Information

• Chemical Name: NO-aspirin
• CAS No.: 287118-97-2
• Molecular Formula: C₁₆H₁₃NO₇
• Molecular Weight: 331.282
• European Community (EC) Number: 803-622-8
• DSSTox Substance ID: DTXSID60431311
• Wikidata: Q82245165
• ChEMBL ID: CHEMBL228226
• Mol file: 287118-97-2.mol

Synonyms:NCX 4040;NCX-4040;NCX4040

Chemical Property of NO-aspirin

Chemical Property:

• Melting Point: 83-86°C
• Boiling Point: 495.7±40.0 °C(Predicted)
• PSA: 107.65000
• Density: 1.347±0.06 g/cm3(Predicted)
• LogP: 3.06260
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble15mg/mL (clear solution)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 331.06920175
• Heavy Atom Count: 24
• Complexity: 454

Purity/Quality:

98%,99%, ^*data from raw suppliers

NO-Aspirin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41-43
• Safety Statements: 26-36/37-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CC=CC=C1C(=O)OC2=CC=C(C=C2)CO[N+](=O)[O-]
• Uses: A novel nitric oxide-releasing aspirin,

Technology Process of NO-aspirin

There total 8 articles about NO-aspirin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

2-acetyloxybenzoic acid 4-hydroxymethylphenyl ester (175077-14-2) → [2-(acetyloxy)benzoicacid 4-(nitrooxy methyl)phenyl ester] (287118-97-2)

Guidance literature:

With N-Bromosuccinimide; silver nitrate; triphenylphosphine; In dichloromethane; acetonitrile; at -45 - 20 ℃; for 14h; Inert atmosphere; Schlenk technique;

Reference yield: 55.0%

2-(acetyloxy)benzoic acid 4-(chloromethyl) phenyl ester (410071-22-6) → [2-(acetyloxy)benzoicacid 4-(nitrooxy methyl)phenyl ester] (287118-97-2)

Guidance literature:

With silver nitrate; In acetonitrile; for 12h; Heating;

DOI:10.1021/jm061371e

Reference yield:

aspirin (50-78-2,98201-60-6) → [2-(acetyloxy)benzoicacid 4-(nitrooxy methyl)phenyl ester] (287118-97-2)

Guidance literature:

Multi-step reaction with 5 steps

1: SOCl₂; pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 3.71 g / Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: 76 percent / NaBH₄ / tetrahydrofuran / 1.33 h / 0 °C

4: SOCl₂; pyridine / CH₂Cl₂ / 4.75 h / -30 - 20 °C

5: 55 percent / AgNO₃ / acetonitrile / 12 h / Heating

With pyridine; sodium tetrahydroborate; thionyl chloride; silver nitrate; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jm061371e

upstream raw materials:

2-(acetyloxy)benzoic acid 4-(chloromethyl) phenyl ester

aspirin

4-(2-acetoxybenzoyloxy)benzaldehyde

O-acetylsalicyloyl chloride

Refernces

• 1、 Hulsman, Niels,Medema, Jan Paul,Bos, Carina,Jongejan, Aldo,Leurs, Rob,Smit, Martine J.,De Esch, Iwan J. P.,Richel, Dick,Wijtmans, Maikel. "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". . p. 2424 - 2431. Retrieved 2008/02/03.
• 2、 Chiroli, Valerio,Benedini, Francesca,Ongini, Ennio,Del Soldato, Piero. "Nitric oxide-donating non-steroidal anti-inflammatory drugs: The case of nitroderivatives of aspirin". . p. 441 - 446. Retrieved 2007/10/03.