Bropirimine
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Bropirimine
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CAS No:
56741-95-8
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Formula:
C10H8BrN3O
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Chemical Name:
Bropirimine
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Synonyms:
4(3H)-Pyrimidinone,2-amino-5-bromo-6-phenyl-;4(1H)-Pyrimidinone,2-amino-5-bromo-6-phenyl-;2-Amino-5-bromo-6-phenyl-4(3H)-pyrimidinone;5-Bromo-6-phenylisocytosine;2-Amino-5-bromo-6-phenyl-4-pyrimidinol;NSC 149027;2-Amino-5-bromo-6-phenyl-4-pyrimidinone;5-Bromo-2,3-dihydro-2-imino-6-phenyl-4(1H)-pyrimidinone;Bropirimine;U 54461;U 54461S;PNU 54461;2-Amino-5-bromo-4-hydroxy-6-phenylpyrimidine;2-Amino-5-bromo-6-phenyl-1H-pyrimidin-4-one;2-Amino-5-bromo-6-phenyl-3,4-dihydropyrimidin-4-one
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CAS No:
Description
Bropirimine is a member of pyrimidines.|Bropirimine is an oral immunostimulant that causes the body to produce interferon and other substances.
Characteristics
67.5
1.2
white to beige
1.7±0.1 g/cm3
246-248 °C @ Solvent: Water, Ethanol
389.7°C at 760 mmHg
240.0±31.5 °C
1.696
DMSO: ≥5mg/mL (warm DMSO)
room temp
Oral-rat LD50:>3200 mg/kg
Flammable; burning produces toxic nitrogen oxides and bromide fumes
Safety Information
NONH for all modes of transport
3
63-62
UW7351300
Xn
Warehouse ventilated, low temperature and dry
P281
H361
Drug Information
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Agents that promote the production and release of interferons. They include mitogens, lipopolysaccharides, and the synthetic polymers Poly A-U and Poly I-C. Viruses, bacteria, and protozoa have been also known to induce interferons. (See all compounds classified as Interferon Inducers.)
Bropirimine has known human metabolites that include m-hydroxybropirimine and p-hydroxybropirimine.
2-amino-5-bromophenyl-4-pyrimidinone
Bropirimine Use and Manufacturing
To a suspension of 2-amino-6-phenylpyrimidin-4(3H)-one 6 (200 mg, 1.07 mmol) in glacialacetic acid (2 mL) at 70 °C was slowly added a solution of bromine (57.0 μL, 1.12 mmol) inglacial acetic acid (2 mL). The reaction mixture was allowed to cool to ambient temperature and stirred for 4 h, and then the solvent removed under reduced pressure. The residue was trituratedwith ether (10 mL) and recrystallized from ethanol to give the title compound as a colourlesssolid (171 mg, 60percent); mp 275-277 °C (lit., 2 mp 285-287 °C); (Found: M+H+, 264.9847.C10H979BrN3O+ requires 264.9845); νmax (CHCl3)/cm-1 3691, 3607, 3012, 1692, 1602, 1473, 1440, 1328, 1240; δH (400 MHz; DMSO-d6) 7.56-7.53 (2 H, m, ArH), 7.45-7.43 (3 H, m, ArH), 6.87 (2 H, br s, NH2); δC (100 MHz; DMSO-d6) 158.6 (C), 153.2 (2xC), 136.3 (C), 129.7 (CH), 128.5 (CH), 128.0 (CH), 97.3 (C) ; m/z (ESI) 264/266 (M+H+, 34/35percent).
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.
Computed Properties
Molecular Weight:266.09
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:264.98507
Monoisotopic Mass:264.98507
Topological Polar Surface Area:67.5
Heavy Atom Count:15
Complexity:343
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
