Ozagrel

Ozagrel (INN) is an antiplatelet agent working as a thromboxane A2 synthesis inhibitor.^[1]

Ozagrel

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (2E)-3-[4-(1H-imidazol-1-ylmethyl)phenyl]acrylic acid
CAS Number	82571-53-7 Y
PubChem CID	5282440
ChemSpider	4445594 Y
UNII	L256JB984D
KEGG	D08327 Y
ChEMBL	ChEMBL11662 Y
CompTox Dashboard (EPA)	DTXSID6048547
ECHA InfoCard	100.122.039
Chemical and physical data
Formula	C13H12N2O2
Molar mass	228.251 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC(=CC=C1CN2C=CN=C2)/C=C/C(=O)O
InChI InChI=1S/C13H12N2O2/c16-13(17)6-5-11-1-3-12(4-2-11)9-15-8-7-14-10-15/h1-8,10H,9H2,(H,16,17)/b6-5+ Y Key:SHZKQBHERIJWAO-AATRIKPKSA-N Y

Synthesis

The free-radical halogenation of ethyl 4-methylcinnamate (1) with N-bromosuccinimide in the presence of benzoyl peroxide gives ethyl 4-bromomethylcinnamate (2).^[2] Alkylation of imidazole (3) with this material gives the ethyl ester (4) of the drug, which is saponified to give ozagrel.^[3][4]