Ozagrel

Base Information

• Chemical Name: Ozagrel
• CAS No.: 82571-53-7
• Molecular Formula: C13H12N2O2
• Molecular Weight: 250.232
• European Community (EC) Number: 919-112-4
• UNII: L256JB984D
• DSSTox Substance ID: DTXSID6048547
• Nikkaji Number: J2.539.247G,J34.702G
• Wikipedia: Ozagrel
• Wikidata: Q7116436
• NCI Thesaurus Code: C66288
• Pharos Ligand ID: NQ578NPPN22W
• Metabolomics Workbench ID: 153081
• ChEMBL ID: CHEMBL11662
• Mol file: 82571-53-7.mol

Synonyms:3-(4-(1H-imidazol-1-ylmethyl)phenyl)-2-propenoic acid;4-(1-imidazoylmethyl)cinnamic acid;OKY 046;OKY-046;ozagrel;ozagrel, monohydrochloride;ozagrel, monohydrochloride, (E)-isomer;sodium ozagrel

Chemical Property of Ozagrel

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.47E-09mmHg at 25°C
• Melting Point: 223 - 224oC
• Refractive Index: 1.593
• Boiling Point: 468 °C at 760 mmHg
• PKA: 4.43±0.10(Predicted)
• Flash Point: 236.8 °C
• PSA: 55.12000
• Density: 1.17 g/cm³
• LogP: 2.02920
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 228.089877630
• Heavy Atom Count: 17
• Complexity: 283

Purity/Quality:

99% ^*data from raw suppliers

Ozagrel ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CN2C=CN=C2)C=CC(=O)O
• Isomeric SMILES: C1=CC(=CC=C1CN2C=CN=C2)/C=C/C(=O)O
• Recent ClinicalTrials: A Parallel Group Phase II Study of KCT-0809 in Patients With Dry Eye Syndromes
• Recent NIPH Clinical Trials: The effect of thromboxane A2 (TXA2) synthase inhibitor (Ozagrel) on difficult to treat chough variant asthma (CVA).
• Uses: Strong thromboxane synthetase inhibitors. By inhibiting thromboxane synthase,it reduces the body thromboxane A, (TXA2), and promotes prostacyclin (PGl2) generation to be against aggregation of platelets, and cerebrovascular spasm, and it almost has no effect on cyclooxygenase and other arachidonic metabolizing enzymes.it is Clinically used for improving cerebral vasospasm after cobweb inferior vena hemorrhage surgery and symptoms of cerebral ischemia associated with cerebral vasospasm, and dyskinesia associated with cerebral thrombosis acute phase. Ozagrel is a potent and selective thromboxane A2 inhibitor. Used in the prevention of ischemic stroke injury and maintains a strong effect in vascular contraction and vascular endothelial cell dysfunction.
• production method: Use dehydrated methyl benzaldehyde as materials,after condensation with acetic anhydride aldol ,form 3-tolyl acrylate, become into a 3--tolyl acrylate ethyl after esterification , use benzoyl peroxide as an initiator, with N-bromosuccinimide (NBS) ,make the methyl on the ring become into bromomethyl, and after the hydrolysis reaction with imidazole, ozagrel sodium is obtained , melting point 308 ℃ (decomposition).
• Description: Ozagrel sodium is the first thromboxane (TX2) synthetase inhibitor to be developed as an antithrombotic agent. In patients with angina pectoris, ozagrel sodium reportedly decreases the frequency of anginal attacks and increases exercise tolerance. Other indications for ozagrel sodium currently under study include bronchial asthma and pulmonary thromboembolism.

Technology Process of Ozagrel

There total 7 articles about Ozagrel 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: 85.05%

ethyl (E)-3-[4-(imidazol-1-ylmethyl)phenyl]acrylate (78712-80-8) → Cataclot (82571-53-7)

Guidance literature:

With sodium hydroxide; In ethanol; for 2h; Reflux;

Reference yield:

ethyl (E)-3-(4-methylphenyl)acrylate (97585-04-1,20511-20-0,24393-49-5) → Cataclot (82571-53-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,2'-azobis(isobutyronitrile) / acetonitrile / 2 h / 65 - 80 °C

2: sodium hydroxide / tetrahydrofuran / 2.5 h / 10 °C

3: sodium hydroxide / water / 1.5 h / 55 °C

With 2,2'-azobis(isobutyronitrile); sodium hydroxide; In tetrahydrofuran; water; acetonitrile;

Reference yield:

4-(1-imidazolylmethyl)cinnamic acid hydrochloride (78712-43-3,74003-18-2) → ozagrel (82571-53-7)

Guidance literature:

With sodium hydroxide; In water; at 20 - 60 ℃; for 2h; Temperature;

upstream raw materials:

ethyl (E)-3-[4-(imidazol-1-ylmethyl)phenyl]acrylate

cis-ozagrel

ethyl (E)-4-(bromomethyl)cinnamate

4-(1-imidazolylmethyl)cinnamic acid hydrochloride

Refernces

• 1、 -. "Preparation method of Ozagrel sodium". . . Retrieved 2018/04/02.
• 2、 Hirayama,Utsuki,Uekama,Yamasaki,Harata. "Prominent inclusion effect of dimethyl-β-cyclodextrin on photoisomerization of the thromboxane synthetase inhibitor (E)-4-(1- imidazoylmethyl)cinnamic acid". . p. 817 - 822. Retrieved 2007/10/02.