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143504-99-8,MFCD00043013
Catalog No.:AA00AHPY

143504-99-8 | 2,6-Diaminopyrimidin-4(3H)-one

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250mg
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$24.00   $17.00
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1g
98%
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$66.00   $46.00
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5g
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$321.00   $225.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00AHPY
Chemical Name:
2,6-Diaminopyrimidin-4(3H)-one
CAS Number:
143504-99-8
Molecular Formula:
C4H6N4O
Molecular Weight:
126.1166
MDL Number:
MFCD00043013
SMILES:
Nc1nc(N)[nH]c(=O)c1
Properties
Computed Properties
 
Complexity:
205  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
XLogP3:
-1.8  

Downstream Synthesis Route

[1]JournalofOrganicChemistry,1983,vol.48,p.4852-4860

[1]BioorganicandMedicinalChemistry,2010,vol.18,p.3575-3587

[1]BioorganicandMedicinalChemistryLetters,2011,vol.21,p.1554-1558

[1]BioorganicandMedicinalChemistryLetters,2011,vol.21,p.1554-1558

[1]BioorganicandMedicinalChemistryLetters,2011,vol.21,p.1554-1558

Literature

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Title: Cocrystals of 5-fluorocytosine. II. Coformers with variable hydrogen-bonding sites.

Journal: Acta crystallographica. Section B, Structural science 20120801

Title: Fluvastatin upregulates endothelial nitric oxide synthase activity via enhancement of its phosphorylation and expression and via an increase in tetrahydrobiopterin in vascular endothelial cells.

Journal: International journal of cardiology 20120405

Title: Correlations between Endothelial Functions and ROS Detection in Diabetic Microvascular Wall: Early and Late Ascorbic Acid Supplementation.

Journal: International journal of vascular medicine 20120101

Title: Decreased tetrahydrobiopterin and disrupted association of Hsp90 with eNOS by hyperglycemia impair myocardial ischemic preconditioning.

Journal: American journal of physiology. Heart and circulatory physiology 20111101

Title: Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-glycinamide ribonucleotide formyltransferase.

Journal: Journal of medicinal chemistry 20111027

Title: Activation of peroxisome proliferator-activated receptor-{delta} enhances regenerative capacity of human endothelial progenitor cells by stimulating biosynthesis of tetrahydrobiopterin.

Journal: Hypertension (Dallas, Tex. : 1979) 20110801

Title: Pseudopolymorphs of 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one: one or two tautomers present in the same crystal.

Journal: Acta crystallographica. Section C, Crystal structure communications 20110501

Title: Substrate-controlled chemoselective synthesis and potent cytotoxic activity of novel 5,6,7-triarylpyrido[2,3-d]pyrimidin-4-one derivatives.

Journal: Bioorganic & medicinal chemistry letters 20110301

Title: Two new polymorphs of 2,6-diaminopyrimidin-4(3H)-one monohydrate.

Journal: Acta crystallographica. Section C, Crystal structure communications 20110101

Title: Validity of urinary monoamine assay sales under the 'spot baseline urinary neurotransmitter testing marketing model'.

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Title: Design, synthesis and evaluation of 2-amino-4-m-bromoanilino-6-arylmethyl-7H-pyrrolo[2,3-d]pyrimidines as tyrosine kinase inhibitors and antiangiogenic agents.

Journal: Bioorganic & medicinal chemistry 20100715

Title: Synthesis and biological activity of N(4)-phenylsubstituted-6-(2,4-dichloro phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamines as vascular endothelial growth factor receptor-2 inhibitors and antiangiogenic and antitumor agents.

Journal: Bioorganic & medicinal chemistry 20100515

Title: Tetrahydrobiopterin (BH4), a cofactor for nNOS, restores gastric emptying and nNOS expression in female diabetic rats.

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Title: Novel riboswitch ligand analogs as selective inhibitors of guanine-related metabolic pathways.

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Title: Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier for cellular entry.

Journal: Journal of medicinal chemistry 20100211

Title: Role of tetrahydrobiopterin in resistance to myocardial ischemia in Brown Norway and Dahl S rats.

Journal: American journal of physiology. Heart and circulatory physiology 20091101

Title: DFT simulations and vibrational analysis of FT-IR and FT-Raman spectra of 2,4-diamino-6-hydroxypyrimidine.

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Title: Metallothionein abrogates GTP cyclohydrolase I inhibition-induced cardiac contractile and morphological defects: role of mitochondrial biogenesis.

Journal: Hypertension (Dallas, Tex. : 1979) 20090601

Title: Highly diastereoselective domino synthesis of 6-spirosubstituted pyrido[2,3-d]pyrimidine derivatives in water.

Journal: Journal of combinatorial chemistry 20090101

Title: Acute inhibition of guanosine triphosphate cyclohydrolase 1 uncouples endothelial nitric oxide synthase and elevates blood pressure.

Journal: Hypertension (Dallas, Tex. : 1979) 20080901

Title: Three-day tetrahydrobiopterin therapy increases in vivo hepatic NOS activity and reduces portal pressure in CCl4 cirrhotic rats.

Journal: Journal of hepatology 20080801

Title: Effect of decreased levels of intrinsic tetrahydrobiopterin on endothelial function in anesthetized rats.

Journal: Journal of pharmacological sciences 20080501

Title: 2,4-Diamino-6-hydroxypyrimidine (DAHP) suppresses cytokine-induced VCAM-1 expression on the cell surface of human umbilical vein endothelial cells in a BH(4)-independent manner.

Journal: Biochimica et biophysica acta 20080101

Title: Regulation of tetrahydrobiopterin biosynthesis by shear stress.

Journal: Circulation research 20071012

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Journal: PLoS genetics 20071001

Title: An efficient route for the synthesis of a new class of pyrido[2,3-d]pyrimidine derivatives.

Journal: Organic & biomolecular chemistry 20070507

Title: C-Reactive protein-induced endothelial microparticle generation in HUVECs is related to BH4-dependent NO formation.

Journal: Journal of vascular research 20070101

Title: Folic acid reverses endothelial dysfunction induced by inhibition of tetrahydrobiopterin biosynthesis.

Journal: European journal of pharmacology 20060120

Title: Neural tube closure depends on nitric oxide synthase activity.

Journal: Journal of neurochemistry 20060101

Title: Estrogen therapy replenishes vascular tetrahydrobiopterin and reduces oxidative stress in ovariectomized rats.

Journal: Menopause (New York, N.Y.) 20060101

Title: Synthesis and antitumor activity of some novel quinazoline derivatives bearing the biologically active thione moiety.

Journal: Arzneimittel-Forschung 20060101

Title: Tetrahydrobiopterin depletion and ubiquitylation of neuronal nitric oxide synthase.

Journal: Brain research. Molecular brain research 20051207

Title: Inhibition of brain GTP cyclohydrolase I and tetrahydrobiopterin attenuates cerebral infarction via reducing inducible NO synthase and peroxynitrite in ischemic stroke.

Journal: Stroke 20051201

Title: Immobilization stress causes increases in tetrahydrobiopterin, dopamine, and neuromelanin and oxidative damage in the nigrostriatal system.

Journal: Journal of neurochemistry 20051001

Title: Crystal structure and luminescence of lanthanide monodentate complexes [Ln(C(4)N(4)H(6)O)(2)(H(2)O)(6)]Cl(3) and [Ln(C(4)N(4)H(6)O)(2)(H(2)O)(3)(NO(3))(3)] (Ln = Tb or Eu).

Journal: Inorganic chemistry 20050613

Title: Synthesis of classical, three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogues as antifolates.

Journal: Journal of medicinal chemistry 20041230

Title: Effect of tetrahydrobiopterin on nitric oxide synthase-containing cells in the rat hippocampus.

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Title: The mechanism of potent GTP cyclohydrolase I inhibition by 2,4-diamino-6-hydroxypyrimidine: requirement of the GTP cyclohydrolase I feedback regulatory protein.

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Title: A new and efficient synthesis of pyrrolo[2,3-d]pyrimidine anticancer agents: Alimta (LY231514, MTA), homo-Alimta, TNP-351, and some aryl 5-substituted pyrrolo[2,3-d]pyrimidines.

Journal: The Journal of organic chemistry 20031226

Title: Tetrahydrobiopterin, a critical factor in the production and role of nitric oxide in mast cells.

Journal: The Journal of biological chemistry 20031212

Title: Antiangiogenic and antitumor agents. Design, synthesis, and evaluation of novel 2-amino-4-(3-bromoanilino)-6-benzylsubstituted pyrrolo[2,3-d]pyrimidines as inhibitors of receptor tyrosine kinases.

Journal: Bioorganic & medicinal chemistry 20031117

Title: GTP cyclohydrolase 1 inhibition attenuates vasodilation and increases blood pressure in rats.

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Title: Exogenous biopterins requirement for iNOS function in vascular smooth muscle cells.

Journal: Journal of cardiovascular pharmacology 20030801

Title: Kainic acid lesion-induced nigral neuronal death.

Journal: Journal of chemical neuroanatomy 20030801

Title: Interactions of peroxynitrite, tetrahydrobiopterin, ascorbic acid, and thiols: implications for uncoupling endothelial nitric-oxide synthase.

Journal: The Journal of biological chemistry 20030620

Title: Tetrahydrobiopterin precursor sepiapterin provides protection against neurotoxicity of 1-methyl-4-phenylpyridinium in nigral slice cultures.

Journal: Journal of neurochemistry 20030401

Title: HMG-CoA reductase inhibitor increases GTP cyclohydrolase I mRNA and tetrahydrobiopterin in vascular endothelial cells.

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Title: Role of tetrahydrobiopterin on ischemia-reperfusion injury in isolated perfused rat hearts.

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Journal: Cardiovascular pathology : the official journal of the Society for Cardiovascular Pathology 20030101

Title: Lack of nitric oxide mediation of flow-dependent arteriolar dilation in type I diabetes is restored by sepiapterin.

Journal: Journal of vascular research 20030101

Title: Effect of 2,4-diamino-6-hydroxy-pyrimidine on postburn Staphylococcus aureus sepsis in rats.

Journal: Critical care medicine 20021101

Title: Stimulation of tetrahydrobiopterin synthesis by cyclosporin A in mouse brain microvascular endothelial cells.

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Title: Tetrahydrobiopterin deficiency increases neuronal vulnerability to hypoxia.

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Title: Cellular basis of endothelial dysfunction in small mesenteric arteries from spontaneously diabetic (db/db -/-) mice: role of decreased tetrahydrobiopterin bioavailability.

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Journal: Zhonghua shao shang za zhi = Zhonghua shaoshang zazhi = Chinese journal of burns 20020401

Title: 2, 4-diamino-6- hydroxy pyrimidine inhibits NSAIDs induced nitrosyl-complex EPR signals and ulcer in rat jejunum.

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Title: Guanosine triphosphate cyclohydrolase I regulates nitric oxide synthesis in renal proximal tubules.

Journal: Journal of the American Society of Nephrology : JASN 19950201

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Tags:143504-99-8 Molecular Formula|143504-99-8 MDL|143504-99-8 SMILES|143504-99-8 2,6-Diaminopyrimidin-4(3H)-one