Chemistry:Bropirimine
From HandWiki
Short description: Chemical compound
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| Formula | C10H8BrN3O |
| Molar mass | 266.098 g·mol−1 |
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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
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
- ↑ "Bropirimine, an orally active anticancer agent for superficial bladder cancer". European Urology 34 (2): 107–10. August 1998. doi:10.1159/000019693. PMID 9693244.
- ↑ "Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents". Journal of Medicinal Chemistry 28 (12): 1864–9. December 1985. doi:10.1021/jm00150a018. PMID 2999405.
- ↑ "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. 1975. doi:10.1039/p19750001023. PMID 1170192.
- ↑ "Structural studies on bioactive compounds. Part 27. Chemistry of the immunomodulatory agent bropirimine". Anti-Cancer Drug Design 10 (3): 215–26. April 1995. PMID 7748456.
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