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Ozagrel

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(Redirected from C13H12N2O2)

Ozagrel
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (2E)-3-[4-(1H-imidazol-1-ylmethyl)phenyl]acrylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.122.039 Edit this at Wikidata
Chemical and physical data
FormulaC13H12N2O2
Molar mass228.251 g·mol−1
3D model (JSmol)
  • C1=CC(=CC=C1CN2C=CN=C2)/C=C/C(=O)O
  • 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+ checkY
  • Key:SHZKQBHERIJWAO-AATRIKPKSA-N checkY

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

Synthesis

[edit]

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]

References

[edit]
  1. ^ Loo MH, Egan D, Vaughan ED, Marion D, Felsen D, Weisman S (March 1987). "The effect of the thromboxane A2 synthesis inhibitor OKY-046 on renal function in rabbits following release of unilateral ureteral obstruction". The Journal of Urology. 137 (3): 571–576. doi:10.1016/s0022-5347(17)44108-5. PMID 3820396.
  2. ^ US 4175203, Cragoe Jr EJ, Bicking JB, "nterphenylene 11,12-secoprostaglandins", issued 20 November 1979, assigned to to Merck and Co Inc 
  3. ^ Iizuka K, Akahane K, Momose D, Nakazawa M, Tanouchi T, Kawamura M, et al. (October 1981). "Highly selective inhibitors of thromboxane synthetase. 1. Imidazole derivatives". Journal of Medicinal Chemistry. 24 (10): 1139–1148. doi:10.1021/jm00142a005. PMID 7199088.
  4. ^ "Ozagrel". Pharmaceutical Substances. Georg Thieme Verlag KG. Retrieved 2024-06-30.