Bropirimine

Bropirimine
Clinical data
ATC code none
Identifiers
CAS Number 56741-95-8
ChemSpider 58914
UNII J57CTF25XJ YesY
ChEMBL CHEMBL37387
ECHA InfoCard 100.231.001
Chemical and physical data
Formula C10H8BrN3O
Molar mass 266.09 g/mol
3D model (Jmol) Interactive image

Bropirimine is an experimental drug with anti-cancer and antiviral properties.[1] It is an orally effective immunomodulator and is being tried in bladder cancers.[2]

Synthesis

Bropirimine synthesis:[3] other syntheses:[4][5]

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. ↑ sciencedirect
  2. ↑ http://content.karger.com/ProdukteDB/produkte.asp?Doi=19693
  3. ↑ Skulnick, Harvey I.; Weed, Sheldon D.; Eidson, Emerson E.; Renis, Harold E.; Stringfellow, Dale A.; Wierenga, Wendell (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.
  4. ↑ Brown, Thomas B.; Stevens, Malcolm F. G. (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. doi:10.1039/p19750001023. ISSN 0300-922X.
  5. ↑ M. F. G. Stevens et al., Anti-Cancer Drug Des. 10, 215 (1995).


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