| Identification | Back Directory | [Name]
2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE | [CAS]
56741-95-8 | [Synonyms]
U-54461
U 54461S
PNU-54461
NSC 149027
bropirimine
5-BroMo-6-phenylisocytosine
2-AMino-5-broMo-6-phenyl-4-pyriMidinol
2-Amino-5-bromo-6-phenylpyrimidin-4-ol
2-AMino-5-broMo-6-phenyl-4-pyriMidinone
2-Amino-5-bromo-6-phenyl-4(3H)-pyrimidone
2-amino-5-bromo-6-phenyl-4(1h)-pyrimidinon
2-amino-5-bromo-6-phenyl-4(1h)-pyrimidinone
2-amino-5-bromo-6-phenyl-1H-pyrimidin-4-one
2-AMino-5-broMo-6-phenyl-4(3H)-pyriMidinone
2-Amino-5-bromo-6-phenylpyrimidin-4(1H)-one
2-Amino-5-bromo-6-phenylpyrimidin-4(3H)-one
2-AMINO-4-HYDROXY-5-BROMO-6-PHENYLPYRIMIDINE
2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE
2-Amino-5-bromo-4-phenyl-6-hydroxypyrimidine
4(3H)-PyriMidinone, 2-aMino-5-broMo-6-phenyl-
2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE USP/EP/BP
5-Bromo-6-phenyl-2,3-dihydro-2-iminopyrimidin-4(1H)-one
5-BroMo-2,3-dihydro-2-iMino-6-phenyl-4(1H)-pyriMidinone | [Molecular Formula]
C10H8BrN3O | [MDL Number]
MFCD00813905 | [MOL File]
56741-95-8.mol | [Molecular Weight]
266.09 |
| Chemical Properties | Back Directory | [Melting point ]
285-287° (Stevens); mp 246-248° (Brown, Stevens) | [Boiling point ]
389.7±52.0 °C(Predicted) | [density ]
1.6292 (rough estimate) | [refractive index ]
1.6520 (estimate) | [storage temp. ]
room temp | [solubility ]
DMSO: ≥5mg/mL (warm DMSO) | [form ]
powder | [pka]
3.18; 8.53(at 25℃) | [color ]
white to beige | [Water Solubility ]
7.8mg/L(37 ºC) | [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) | [InChIKey]
CIUUIPMOFZIWIZ-UHFFFAOYSA-N | [SMILES]
NC1=NC(=O)C(Br)=C(N1)c2ccccc2 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
63-62 | [WGK Germany ]
3 | [RTECS ]
UW7351300 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Repr. 2 |
| Hazard Information | Back Directory | [Description]
Bropirimine is an immunomodulator with diverse biological activities. It is a toll-like receptor 7 (TLR7) agonist that inhibits RANKL-induced osteoclast differentiation of murine bone marrow-derived macrophages (BMDMs) in a concentration-dependent manner, an effect that is reversed by an anti-IFN-β antibody. Dietary administration of bropirimine (200 mg/kg twice per week) prevents development of transitional cell carcinomas (TCCs) in a mouse model of carcinogen-induced bladder carcinoma. Bropirimine (100 mg/kg) reduces pulmonary collagen accumulation and bronchoalveolar lavage fluid (BALF) monocyte and eosinophil infiltration in a hamster model of bleomycin-induced lung fibrosis. It also delays disease onset and progression and increases plasma IFN levels in a mouse model of experimental autoimmune encephalomyelitis (EAE). | [Uses]
Bropirimine is an orally active immunostimulant; anticancer agent. Bropirimine is an interferon inducer that is a potentially useful in the the treatment of superficial bladder cancer (transitional cell carcinoma). Studies suggest that Bropirimine has direct antitumor activity rather than a cytokine-mediated antitumor effect. | [Definition]
ChEBI: Bropirimine is a member of pyrimidines. | [Biochem/physiol Actions]
Bropirimine is an immunostimulating agent. The compound induces production of α and β interferons and enhances NK cell function. Bropirimine has antiproliferative effects in cancer cell lines and tumor growth in in vivo models. | [Synthesis]
General procedure for the synthesis of 2-amino-5-bromo-4-hydroxy-6-phenylpyrimidines from 2-amino-4-hydroxy-6-phenylpyrimidines: to a suspension of 2-amino-6-phenylpyrimidin-4(3H)-one (200 mg, 1.07 mmol) in glacial acetic acid (2 mL) was added slowly and dropwise at 70 °C with bromine (57.0 μL, 1.12 mmol) in a glacial acetic acid (2 mL) solution. The reaction mixture was cooled to room temperature and stirring was continued for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was ground with ether (10 mL) and recrystallized from ethanol to give 2-amino-5-bromo-4-hydroxy-6-phenylpyrimidine as a colorless solid (171 mg, 60% yield). The melting point of the product was 275-277 °C (literature value: 285-287 °C); high resolution mass spectrometry (HRMS) measured value: M+H+, 264.9847 (C10H9 79BrN3O+, calculated value 264.9845); infrared spectra (νmax, CHCl3, cm-1): 3691, 3607, 3012, 1692, 1602 , 1473, 1440, 1328, 1240; NMR hydrogen spectrum (1H NMR, 400 MHz, DMSO-d6): δ 7.56-7.53 (2H, m, ArH), 7.45-7.43 (3H, m, ArH), 6.87 (2H, br s, NH2); NMR carbon spectrum (13C NMR, 100 MHz. DMSO-d6): δ 158.6 (C), 153.2 (2×C), 136.3 (C), 129.7 (CH), 128.5 (CH), 128.0 (CH), 97.3 (C); mass spectrum (ESI): m/z 264/266 (M+H+, 34/35%). The spectral data of the obtained product are in agreement with literature reports. | [storage]
Desiccate at RT | [Toxics Screening Level]
The initial threshold screening level (ITSL) for bropirimine is 15 μg/m3
based
on an annual averaging time. | [References]
[1] Tetrahedron, 2015, vol. 71, # 39, p. 7339 - 7343
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 5, p. 1315 - 1321
[3] Journal of Medicinal Chemistry, 1980, vol. 23, # 3, p. 237 - 239
[4] Journal of Medicinal Chemistry, 1985, vol. 28, # 12, p. 1864 - 1869 |
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