Bropirimine
| Bropirimine | |
|---|---|
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| CAS Number | 56741-95-8 |
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| ChemSpider | 58914 |
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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.[1]
Synthesis[edit | edit source]
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[edit | edit source]
- ↑ , Bropirimine, an Orally Active Anticancer Agent for Superficial Bladder Cancer, European Urology, 1998, Vol. 34(Issue: 2), pp. 107–110, DOI: 10.1159/000019693,
- ↑ , 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,
- ↑ , 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, (Issue: 11), pp. 1023, DOI: 10.1039/p19750001023,
- ↑ , 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,
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