Bropirimine

Bropirimine
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-amino-5-bromo-6-phenylpyrimidin-4(1H)-one;
CAS Number	56741-95-8;
ChemSpider	58914;
UNII	J57CTF25XJ;
ChEMBL	ChEMBL37387;
CompTox Dashboard (EPA)	DTXSID5046803 ;
ECHA InfoCard	100.231.001
Chemical and physical data
Formula	C10H8BrN3O
Molar mass	266.098 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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. 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.

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References

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.
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.
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.
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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[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.

[BrownStevens1975-3] 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.