65996-50-1

Basic information

• Product Name: 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion
• Synonyms: 1,5-DIHYDRO-PYRROLO[3,2-A]PYRIMIDINE-2,4-DIONE;1,5-DIHYDRO-PYRROLO[3,2-D]PYRIMIDINE-2,4-DIONE;1,5-dihydro-pyrrolo[3,2-a]pyri;1,5-DIHYDROPYRROLO[3,2-A]PYRIMIDINE-2,4-DION;1-Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione;1H,2H,3H,4H,5H-pyrrolo[3,2-d]pyriMidine-2,4-dione;5H-Pyrrolo[3,2-d]pyriMidine-2,4-diol
• CAS NO: 65996-50-1
• Molecular Formula: C₆H₅N₃O₂
• Molecular Weight: 151.12
• Product Categories: Ketone;Bases & Related Reagents;Intermediates;Nucleotides;pyrimidine;Heterocycle-Pyrimidine series
• Mol File: 65996-50-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: >360 °C(Solv: water (7732-18-5))
• Boiling Point: 607.6 °C at 760 mmHg
• Flash Point: 321.2 °C
• Appearance: /
• Density: 1.516 g/cm³
• Vapor Pressure: 2.35E-15mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: 2-8°C
• PKA: 11.32±0.20(Predicted)
• CAS DataBase Reference: 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion(65996-50-1)
• EPA Substance Registry System: 1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion(65996-50-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 65996-50-1(Hazardous Substances Data)

Usage

Uses

1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion is used for the preparation of pyrazolopyrimidine derivatives or analogs thereof as CCR4 function modulators.

InChI:InChI=1/C6H5N3O2/c10-5-4-3(1-2-7-4)8-6(11)9-5/h1-2,7H,(H2,8,9,10,11)

Upstream product

• 116705-41-0 (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4-diol 
• 252932-49-3 3-amino-2-ethoxycarbonylpyrrole hydrochloride 
• 626-48-2 6-Methyluracil 
• 116705-41-0 (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione 
• 939979-34-7 ethyl 3-ureido-1H-pyrrole-2-carboxylate 
• 16632-21-6 5-nitro-6-methyluracil 
• 1560-54-9 allyltriphenylphosphonium bromide 
• 116705-41-0 5-Nitro-2,4-dioxo-6-(β-dimethylaminovinyl)-1,2,3,4-tetrahydropyrimidine 

Downstream Products

• 142544-99-8 C₃₂H₂₅N₃O₉ 
• 63200-54-4 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine 
• 1377432-91-1 tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-7-(pyridin-3-yl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-3-yl)carbamate 
• 1377432-92-2 tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-7-(pyridin-4-yl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-3-yl)carbamate 
• 1377432-93-3 tert-butyl ((3R)-1-(3-(2-cyanobenzyl)-4-oxo-7-(thiophen-3-yl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-3-yl)carbamate 
• 1377432-74-0 2-((2-((R)-3-aminopiperidin-1-yl)-7-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-3-yl)methyl)benzonitrile 
• 1377432-75-1 2-((2-((R)-3-aminopiperidin-1-yl)-4-oxo-7-(pyridin-3-yl)-4H-pyrrolo[3,2-d]pyrimidin-3(5H)-yl)methyl)benzonitrile 
• 1377432-76-2 2-((2-((R)-3-aminopiperidin-1-yl)-4-oxo-7-(pyridin-4-yl)-4H-pyrrolo[3,2-d]pyrimidin-3(5H)-yl)methyl)benzonitrile 
• 1377432-77-3 2-((2-((R)-3-aminopiperidin-1-yl)-4-oxo-7-(thiophen-3-yl)-4H-pyrrolo[3,2-d]pyrimidin-3(5H)-yl)methyl)benzonitrile 
• 90993-29-6 2-chloro-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one 
• 5451-40-1 2,6 dichloropurine 
• 928841-01-4 5-(benzyloxymethyl)-2,4-dichloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine 
• 114685-01-7 2,4-Bis<(β-cyclohexen-1'-yl)ethylamino>pyrrolo<3,2-d>pyrimidine 
• 114685-02-8 N²,N⁴-Bis-(4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-2,4-diamine 

Relevant articles and documents

Thermodynamic analysis of mRNA cap binding by the human initiation factor eIF4E via free energy perturbations

Eukaryotic mRNAs are appended at the 5′ end, with the 7-methylguanosine cap linked by a 5′-5′-triphosphate bridge to the first transcribed nucleoside (m7GpppX). Initiation of cap-dependent translation of mRNA requires direct interaction between the cap st

Anticancer Properties of Halogenated Pyrrolo[3,2-d]pyrimidines with Decreased Toxicity via N5 Substitution

Halogenated pyrrolo[3,2-d]pyrimidine analogues have shown antiproliferative activity in recent studies, with cell accumulation occurring in the G2/M stage without apoptosis. However, the mechanism of action and pharmacokinetic (PK) profile of these compounds has yet to be determined. To investigate the PK profile of these compounds, a series of halogenated pyrrolo[3,2-d]pyrimidine compounds was synthesized and first tested for activity in various cancer cell lines followed by a mouse model. EC50 values ranged from 0.014 to 14.5 μm, and maximum tolerated doses (MTD) in mice were between 5 and 10 mg kg?1. This indicates a wide variance in activity and toxicity that necessitates further study. To decrease toxicity, a second series of compounds was synthesized with N5-alkyl substitutions in an effort to slow the rate of metabolism, which was thought to be leading to the toxicity. The N-substituted compounds demonstrated comparable cell line activity (EC50 values between 0.83–7.3 μm) with significantly decreased toxicity (MTD=40 mg kg?1). Finally, the PK profile of the active N5-substituted compound shows a plasma half-life of 32.7 minutes, and rapid conversion into the parent unsubstituted analogue. Together, these data indicate that halogenated pyrrolo[3,2-d]pyrimidines present a promising lead into potent antiproliferative agents with tunable activity and toxicity, and rapid metabolism.

Pyrrolopyrimidine ketone compound and preparation method and application thereof

The invention relates to a pyrrolopyrimidine ketone compound and a preparation method and application thereof, and belongs to the technical field of medicine. The pyrrolopyrimidine ketone compound having a structural feature of formula I, or a pharmaceutically acceptable salt thereof has a very good inhibition effect on DPP-IV, and almost no effect on activity of DPP-VIII and DPP-IX, can effectively control the blood glucose concentration of diabetic rats, and is safe and low in toxicity through the verification of pharmacological and toxicological tests. After being prepared into a medicine, the compound provided by the invention not only has an obvious efficacy but also has very small side effects, thus greatly improving the administration convenience and patient use compliance, therefore, the compound has obvious advantages compared with the same kind of medicine. The formula is shown in the specification.