Bropirimine

Chemical compound
  • none
Identifiers
  • 2-amino-5-bromo-6-phenylpyrimidin-4(1H)-one
CAS Number
  • 56741-95-8
ChemSpider
  • 58914
UNII
  • J57CTF25XJ
ChEMBL
  • ChEMBL37387
CompTox Dashboard (EPA)
  • DTXSID5046803 Edit this at Wikidata
ECHA InfoCard100.231.001 Edit this at WikidataChemical and physical dataFormulaC10H8BrN3OMolar mass266.098 g·mol−13D model (JSmol)
  • Interactive image
  • Br\C2=C(/c1ccccc1)N\C(=N/C2=O)N
InChI
  • 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.[citation needed] It is an orally effective immunomodulator and is being tried in bladder cancers.[1]

Synthesis

Bropirimine synthesis:[2] other syntheses:[3][4]

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.

References

  1. ^ Akaza H, Kotake T, Machida T (August 1998). "Bropirimine, an orally active anticancer agent for superficial bladder cancer". European Urology. 34 (2): 107–10. doi:10.1159/000019693. PMID 9693244. S2CID 46069874.
  2. ^ Skulnick HI, Weed SD, Eidson EE, Renis HE, Wierenga W, Stringfellow DA (December 1985). "Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents". Journal of Medicinal Chemistry. 28 (12): 1864–9. doi:10.1021/jm00150a018. PMID 2999405.
  3. ^ Brown TB, Stevens MF (1975). "Triazines and related products. Part XV. 2,4-Diaminopyrimidines and 2-aminopyrimidin-4(3H)-ones bearing 1,2,3-benzotriazinyl groups as potential dihydrofolic reductase inhibitors". Journal of the Chemical Society, Perkin Transactions 1 (11): 1023–8. doi:10.1039/p19750001023. PMID 1170192.
  4. ^ Stevens MF, Baig GU, Gate EN, Wheelhouse RT (April 1995). "Structural studies on bioactive compounds. Part 27. Chemistry of the immunomodulatory agent bropirimine". Anti-Cancer Drug Design. 10 (3): 215–26. PMID 7748456.


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