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Experimental cancer drugs
Bropirimine
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Bropirimine

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Bropirimine
Bropirimine structure.png
Clinical data
ATC code
  • none
Identifiers
  • 2-amino-5-bromo-6-phenylpyrimidin-4(1H)-one
CAS Number
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.231.001
Chemical and physical data
Formula C10H8BrN3O
Molar mass 266.098 g·mol−1
3D model (JSmol)
  • Br\C2=C(/c1ccccc1)N\C(=N/C2=O)N
  • InChI=1S/C10H8BrN3O/c11-7-8(6-4-2-1-3-5-6)13-10(12)14-9(7)15/h1-5H,(H3,12,13,14,15)
  • Key:CIUUIPMOFZIWIZ-UHFFFAOYSA-N

Bropirimine is an experimental drug with anti-cancer and antiviral properties. It is an orally effective immunomodulator and is being tried in bladder cancers.

Synthesis

Bropirimine synthesis: other syntheses:

For the first step, the dianion from malonic acid half-ester is formed by treatment with butyllithium. Acylation of the anion with benzoyl chloride proceeds at the carbanion, which is more nucleophilic (because of the higher charge density). This tricarbonyl compound decarboxylates on acidification to the β-ketoester. Condensation with guanidine leads to the pyrimidone. NBS mediated bromination then gives bropirimine.



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