56741-95-8

Basic information

• Product Name: 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE
• Synonyms: 2-AMINO-4-HYDROXY-5-BROMO-6-PHENYLPYRIMIDINE;2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE;2-amino-5-bromo-6-phenyl-4(1h)-pyrimidinon;2-amino-5-bromo-6-phenyl-4(1h)-pyrimidinone;bropirimine;2-Amino-5-bromo-6-phenylpyrimidin-4(1H)-one;5-Bromo-6-phenyl-2,3-dihydro-2-iminopyrimidin-4(1H)-one;PNU-54461
• CAS NO: 56741-95-8
• Molecular Formula: C₁₀H₈BrN₃O
• Molecular Weight: 266.09
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycle-Pyrimidine series
• Mol File: 56741-95-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 285-287° (Stevens); mp 246-248° (Brown, Stevens)
• Boiling Point: 389.7 °C at 760 mmHg
• Flash Point: 189.5 °C
• Appearance: white to beige/
• Density: 1.6292 (rough estimate)
• Vapor Pressure: 2.8E-06mmHg at 25°C
• Refractive Index: 1.6520 (estimate)
• Storage Temp.: room temp
• Solubility: DMSO: ≥5mg/mL (warm DMSO)
• PKA: 3.18; 8.53(at 25℃)
• Water Solubility: 7.8mg/L(37 oC)
• CAS DataBase Reference: 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE(56741-95-8)
• EPA Substance Registry System: 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE(56741-95-8)

Safety Data

• Hazard Codes: Xn
• Statements: 63-62
• WGK Germany: 3
• RTECS: UW7351300
• Hazardous Substances Data: 56741-95-8(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 56741-95-8 differently. You can refer to the following data:
1. 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.
2. Bropirimine, an immunostimulating agent and toll like receptor (TLR7) agonist, is used in comparison with other TLR7 agonists such as imiquimod, R-848, loxoribine in interferon cell signaling research. Bropirimine may be used in experimental autoimmune encephalomyelitis (EAE) and bladder cancer research.

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.

InChI:InChI=1/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)

Upstream product

• 1402242-62-9 potassium trifluoro(3-oxo-3-phenylprop-1-yn-1-yl)borate 
• 93-58-3 benzoic acid methyl ester 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 98-88-4 benzoyl chloride 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 56741-94-7 2-amino-6-phenyl-3H-pyrimidin-4-one 

Downstream Products

• 102649-59-2 2-succinimido-5-bromo-6-phenyl-4(3H)-pyrimidinone 
• 154379-07-4 5-bromo-2-ethoxycarbonylamino-6-phenyl-4(3H)-pyrimidinone 
• 66376-75-8 2-amino-5,6-diphenylpyrimidin-4(3H)-one 
• 154379-19-8 7-bromo-1-ethoxycarbonylmethyl-4,6-dioxo-8-phenyl-2,3,4,6-tetrahydro-1H-pyrimido<1,2-a>pyrimidine 
• 106791-93-9 2-amino-5-bromo-4-chloro-6-phenylpyrimidine 
• 56741-94-7 2-amino-6-phenyl-3H-pyrimidin-4-one 
• 154379-13-2 7-bromo-4,6-dioxo-8-phenyl-2,3,4,6-tetrahydro-1H-pyrimido<1,2-a>pyrimidine 
• 74856-68-1 2-(acetylamino)-5-bromo-6-phenyl-4(3H)-pyrimidinone 
• 282543-44-6 2-amino-4-methoxy-5-(4-methoxyphenyl)-6-phenylpyrimidine 

Relevant articles and documents

Pyrimidin-6-yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis

We report a novel and general method to access a highly under-studied privileged scaffold—pyrimidines bearing a trifluoroborate at C4, and highlight the broad utility of these intermediates in a rich array of downstream functionalization reactions. This chemistry is underpinned by the unique features of the trifluoroborate group; its robustness provides an opportunity to carry out chemoselective reactions at other positions on the pyrimidine while providing a pathway for elaboration at the C?B bond when suitably activated.

HTS followed by NMR based counterscreening. Discovery and optimization of pyrimidones as reversible and competitive inhibitors of xanthine oxidase

The identification of novel, non-purine based inhibitors of xanthine oxidase is described. After a high-throughput screening campaign, an NMR based counterscreen was used to distinguish actives, which interact with XO in a reversible manner, from assay artefacts. This approach identified pyrimidone 1 as a reversible and competitive inhibitor with good lead-like properties. A hit to lead campaign gave compound 41, a nanomolar inhibitor of hXO with efficacy in the hyperuricemic rat model after oral dosing.

5-Substituted 2-amino-6-phenyl-4(3H)-pyrimidinones. Antiviral- and interferon-inducing agents

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