Bropirimine

Bropirimine
File:Bropirimine structure.png
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number	56741-95-8
PubChem
DrugBank
ChemSpider	58914
KEGG

Bropirimine is an experimental drug with anti-cancer and antiviral properties. ^{(January 2019)}

It is an orally effective immunomodulator and is being tried in bladder cancers.<ref>, 
 Bropirimine, an Orally Active Anticancer Agent for Superficial Bladder Cancer, 
 European Urology, 
 1998,
 Vol. 34(Issue: 2),
 pp. 107–110,
 DOI: 10.1159/000019693,</ref>

Synthesis

File:Bropirimine synthesis.png

Bropirimine synthesis:<ref>, Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents, Journal of Medicinal Chemistry, 1985, Vol. 28(Issue: 12), pp. 1864–1869, DOI: 10.1021/jm00150a018,</ref> other syntheses:<ref name="BrownStevens1975">, 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, 1975, pp. 1023, DOI: 10.1039/p19750001023,</ref><ref>, Structural studies on bioactive compounds. Part 27. Chemistry of the immunomodulatory agent bropirimine, Anti-Cancer Drug Design, 1995, Vol. 10(Issue: 3), pp. 215–26, PMID: 7748456,</ref>

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

File:WHO Rod.svg This article is a medical stub. You can help WikiMD by expanding it!
Most recent articles Ongoing trials	Wikipedia

Stub icon

   This article is a medical stub. You can help WikiMD by expanding it!