Bropirimine

Structural formula
General
Non-proprietary name	Bropirimine
other names	2-Amino-5-bromo-6-phenyl-4 (3 H ) -pyrimidinone 5-Bromo-2-imino-6-phenyl-2,3-dihydropyrimidin-4-one NSC149027 PNU54461 U54461 U54461S
Molecular formula	C 10 H 8 BrN 3 O
Brief description	colorless to beige powder
External identifiers / databases
CAS number 56741-95-8 EC number 804-270-8 ECHA InfoCard 100.231.001 PubChem 65457 ChemSpider 58914 DrugBank DB04168 Wikidata Q4975364
Drug information
Drug class	Immunomodulator , cytostatic agent
properties
Molar mass	266.09 g mol −1
Physical state	firmly
Melting point	285-287 ° C from 2-ethoxyethanol, 246-248 ° C from aqueous ethanol
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 361 P: 281
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bropirimine is a chemical compound from the group of 4-pyrimidinones and a guanosine - analog , the Toll-like receptors of the type 7 is activated (TLR 7).

properties

Bropirimin is used as an agonist of TLR 7 to study the formation of interferons in the course of the immune response . Alternative TLR 7 agonists are imiquimod , resiquimod and loxoribine .

synthesis

Various syntheses of bropirimine have been reported.

The last two steps in the synthesis of bropirimine

In the first step, the dianion of the malonic acid half- ester is formed by treatment with butyllithium . Then carried out acylation of the anion with benzoyl chloride in the carbanion , which due to the higher charge density nucleophilic is. This tricarbonyl compound decarboxylates to the β- keto ester when the pH value is lowered . A condensation with guanidine leads to the pyrimidone . A bromination with N-bromosuccinimide produces bropirimine.

Individual evidence

1. ↑ ^{a b c d e} Sigma-Aldrich : Bropirimine, ≥98% (HPLC) .
2. ↑ Merck Index 13
3. ↑ ^{a b c} Harvey I. Skulnick, Sheldon D. Weed, Emerson E. Eidson, Harold E. Renis, Dale A. Stringfellow, Wendell Wierenga: Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4 (3H) -pyrimidinones. Interferon-inducing antiviral agents . In: Journal of Medicinal Chemistry . 28, No. 12, 1985, pp. 1864-1869. doi : 10.1021 / jm00150a018 .
4. ↑ Thomas B. Brown, Malcolm FG Stevens: 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 . In: Journal of the Chemical Society, Perkin Transactions 1 . No. 11, 1975, p. 1023. doi : 10.1039 / p19750001023 .
5. ^ MF Stevens, GU Baig, EN Gate, RT Wheelhouse: Structural studies on bioactive compounds. Part 27. Chemistry of the immunomodulatory agent bropirimine . In: Anti-Cancer Drug Design . 10, No. 3, 1995, pp. 215-26. PMID 7748456 .