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.
Referencesedit
^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.
^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.
bropirimine, experimental, drug, with, anti, cancer, antiviral, properties, citation, needed, orally, effective, immunomodulator, being, tried, bladder, cancers, clinical, dataatc, codenoneidentifiersiupac, name, amino, bromo, phenylpyrimidin, onecas, number56. 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 BropirimineClinical dataATC codenoneIdentifiersIUPAC name 2 amino 5 bromo 6 phenylpyrimidin 4 1H oneCAS Number56741 95 8ChemSpider58914UNIIJ57CTF25XJChEMBLChEMBL37387CompTox Dashboard EPA DTXSID5046803ECHA InfoCard100 231 001Chemical and physical dataFormulaC 10H 8Br N 3OMolar mass266 098 g mol 13D model JSmol Interactive imageSMILES Br C2 C c1ccccc1 N C N C2 O NInChI 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 NSynthesis edit nbsp 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 b ketoester Condensation with guanidine leads to the pyrimidone NBS mediated bromination then gives bropirimine References edit 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 nbsp This antineoplastic or immunomodulatory drug article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Bropirimine amp oldid 1137629906, wikipedia, wiki, book, books, library,
