Structure via PubChem · Public domain (PubChem)
bropirimine
Sign in to saveBropirimine is an experimental drug with anti-cancer and antiviral properties. It is an orally effective immunomodulator and is being tried in bladder cancers.
Chemical data
- Formula
- C10H8BrN3O
- Molecular weight
- 266.09 g/mol
- IUPAC name
- 2-amino-5-bromo-6-phenyl-1H-pyrimidin-4-one
- SMILES
- C1=CC=C(C=C1)C2=C(C(=O)N=C(N2)N)Br
- InChIKey
- CIUUIPMOFZIWIZ-UHFFFAOYSA-N
- XLogP
- 1.2
- Polar surface area
- 67.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
104 papersvia PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 264.985
Show 2 more facts
- chemical formula
- C₁₀H₈BrN₃O
- canonical SMILES
- C1=CC=C(C=C1)C2=C(C(=O)N=C(N2)N)Br
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
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== 700px|center|thumb|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.
Excerpted from Wikipedia’s “bropirimine” article, available under the CC BY-SA 4.0 licence.