591-54-8 | 4-Aminopyrimidine

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$7.00	$5.00
1g	>98%	in stock	$15.00	$10.00
5g	97%	in stock	$40.00	$28.00
10g	97%	in stock	$48.00	$34.00
25g	97%	in stock	$119.00	$84.00
100g	97%	in stock	$423.00	$296.00
500g	97%	in stock	$1,668.00	$1,168.00

Description

• Catalog Number: AI53230
• Chemical Name: 4-Aminopyrimidine
• CAS Number: 591-54-8
• Molecular Formula: C4H5N3
• Molecular Weight: 95.1026
• MDL Number: MFCD00006112
• SMILES: Nc1ccncn1
• NSC Number: 401236

Computed Properties

• Complexity: 54.9
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 7
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• XLogP3: -0.2

Literature

• Glyoxylate carboligase: a unique thiamin diphosphate-dependent enzyme that can cycle between the 4'-aminopyrimidinium and 1',4'-iminopyrimidine tautomeric forms in the absence of the conserved glutamate.

  Biochemistry 20121009

• Consequences of one-electron oxidation and one-electron reduction for 4-aminopyrimidine--DFT studies.

  Journal of molecular modeling 20120801

• Design, synthesis and antiproliferative activity of 2-acetamidothiazole-5-carboxamide derivatives.

  Medicinal chemistry (Shariqah (United Arab Emirates)) 20120701

• Bifunctionality of the thiamin diphosphate cofactor: assignment of tautomeric/ionization states of the 4'-aminopyrimidine ring when various intermediates occupy the active sites during the catalysis of yeast pyruvate decarboxylase.

  Journal of the American Chemical Society 20120227

• 2-Chloro-pyrimidin-4-amine.

  Acta crystallographica. Section E, Structure reports online 20120201

• Solid-state nuclear magnetic resonance studies delineate the role of the protein in activation of both aromatic rings of thiamin.

  Journal of the American Chemical Society 20120111

• Lead generation of heat shock protein 90 inhibitors by a combination of fragment-based approach, virtual screening, and structure-based drug design.

  Bioorganic & medicinal chemistry letters 20111001

• Coupling reaction between electron-rich pyrimidinones and α-amino acids promoted by phosphonium salts.

  Organic & biomolecular chemistry 20110907

• Application of butenonyl-C-glucosides in the synthesis of pyrazolinyl-, aminopyrimidinyl- and biphenyl methyl-β-D-C-glucopyranosides.

  Molecular diversity 20110801

• Synthesis and biological activities of 2-amino-thiazole-5-carboxylic acid phenylamide derivatives.

  Archiv der Pharmazie 20110701

• Discovery of piperidinyl aminopyrimidine derivatives as IKK-2 inhibitors.

  Bioorganic & medicinal chemistry letters 20110515

• Solid-state NMR and density functional theory studies of ionization states of thiamin.

  The journal of physical chemistry. B 20110203

• Exploration of piperidine-4-yl-aminopyrimidines as HIV-1 reverse transcriptase inhibitors. N-Phenyl derivatives with broad potency against resistant mutant viruses.

  Bioorganic & medicinal chemistry letters 20101015

• Does stacking restrain the photodynamics of individual nucleobases?

  Journal of the American Chemical Society 20100623

• Communication between thiamin cofactors in the Escherichia coli pyruvate dehydrogenase complex E1 component active centers: evidence for a 'direct pathway' between the 4'-aminopyrimidine N1' atoms.

  The Journal of biological chemistry 20100409

• 7-(4-Bromo-phen-yl)-9-phenyl-7H-pyrrolo[3,2-e]tetra-zolo[1,5-c]pyrimidine.

  Acta crystallographica. Section E, Structure reports online 20100301

• Asymmetry in the N-inversion of heteroarene imines: pyrimidin-4(3H)-imine, pyridin-2(1H)-imine, and 1H-purine-6(9H)-imine.

  The Journal of organic chemistry 20100219

• Regulation of the spontaneous augmentation of Na(V)1.9 in mouse dorsal root ganglion neurons: effect of PKA and PKC pathways.

  Marine drugs 20100101

• Somatostatin release, electrical activity, membrane currents and exocytosis in human pancreatic delta cells.

  Diabetologia 20090801

• Reaction mechanisms of thiamin diphosphate enzymes: defining states of ionization and tautomerization of the cofactor at individual steps.

  The FEBS journal 20090501

• Reaction mechanisms of thiamin diphosphate enzymes: new insights into the role of a conserved glutamate residue.

  The FEBS journal 20090501

• Pre-synaptic nicotinic and D receptors functionally interact on dopaminergic nerve endings of rat and mouse nucleus accumbens.

  Journal of neurochemistry 20090301

• The identification of orally bioavailable thrombopoietin agonists.

  Bioorganic & medicinal chemistry letters 20090301

• Investigation of the effects of the novel anticonvulsant compound carisbamate (RWJ-333369) on rat piriform cortical neurones in vitro.

  British journal of pharmacology 20090301

• Two structurally distinct inhibitors of glycogen synthase kinase 3 induced centromere positive micronuclei in human lymphoblastoid TK6 cells.

  Mutation research 20080825

• Nonadiabatic deactivation of 9H-adenine: a comprehensive picture based on mixed quantum-classical dynamics.

  Journal of the American Chemical Society 20080528

• A DFT study of solvation effects on the tautomeric equilibrium and catalytic ylide generation of thiamin models.

  Journal of computational chemistry 20080501

• A study on the inhibition of adenosine deaminase.

  Journal of enzyme inhibition and medicinal chemistry 20080401

• New evidence for cofactor's amino group function in thiamin catalysis by transketolase.

  Biochemical and biophysical research communications 20080215

• Amino-imino tautomerization reaction of the 4-aminopyrimidine/acetic acid system.

  Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20080201

• Elucidation of the chemistry of enzyme-bound thiamin diphosphate prior to substrate binding: defining internal equilibria among tautomeric and ionization states.

  Biochemistry 20070918

• Sodium currents in mesencephalic trigeminal neurons from Nav1.6 null mice.

  Journal of neurophysiology 20070801

• Can the nonadiabatic photodynamics of aminopyrimidine be a model for the ultrafast deactivation of adenine?

  The journal of physical chemistry. A 20070419

• Thiamin deprotonation mechanism. Carbanion development stabilized by the LUMOs of thiazolium and pyrimidylimine working in tandem and release governed by a H-bond switch.

  The journal of physical chemistry. A 20070322

• 4-Aminopyrimidines as novel HIV-1 inhibitors.

  Bioorganic & medicinal chemistry letters 20070101

• Acetylphosphinate is the most potent mechanism-based substrate-like inhibitor of both the human and Escherichia coli pyruvate dehydrogenase components of the pyruvate dehydrogenase complex.

  Bioorganic chemistry 20061201

• Pharmacology of a slowly inactivating outward current in hippocampal CA3 pyramidal neurons.

  Journal of neurophysiology 20060901

• Electronic and nuclear magnetic resonance spectroscopic features of the 1',4'-iminopyrimidine tautomeric form of thiamin diphosphate, a novel intermediate on enzymes requiring this coenzyme.

  Biochemistry 20060620

• Structural and functional alterations of spinal cord axons in adult Long Evans Shaker (LES) dysmyelinated rats.

  Experimental neurology 20050601

• Discovery of pyrimidyl-5-hydroxamic acids as new potent histone deacetylase inhibitors.

  European journal of medicinal chemistry 20050601

• Effect of coenzyme modification on the structural and catalytic properties of wild-type transketolase and of the variant E418A from Saccharomyces cerevisiae.

  The FEBS journal 20050301

• Formation of 4-aminopyrimidines via the trimerization of nitriles using focused microwave heating.

  Journal of combinatorial chemistry 20050101

• Properties of Xenopus Kv1.10 channels expressed in HEK293 cells.

  Journal of neurobiology 20040801

• Tetrahedral intermediates in thiamin diphosphate-dependent decarboxylations exist as a 1',4'-imino tautomeric form of the coenzyme, unlike the michaelis complex or the free coenzyme.

  Biochemistry 20040601

• Over expression of the selectable marker blasticidin S deaminase gene is toxic to human keratinocytes and murine BALB/MK cells.

  BMC biotechnology 20040101

• 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.

  The Journal of organic chemistry 20031226

• Long-lasting anticonvulsant effect of focal cooling on experimental neocortical seizures.

  Epilepsia 20031201

• Dual catalytic apparatus of the thiamin diphosphate coenzyme: acid-base via the 1',4'-iminopyrimidine tautomer along with its electrophilic role.

  Journal of the American Chemical Society 20031022

• Fully automated synthesis module for preparation of S-(2-[(18)F]fluoroethyl)-L-methionine by direct nucleophilic exchange on a quaternary 4-aminopyridinium resin.

  Nuclear medicine and biology 20030701

• Current mechanistic understanding of thiamin diphosphate-dependent enzymatic reactions.

  Natural product reports 20030401

• 2-pyrazinylnitrene and 4-pyrimidylnitrene. Ring expansion to 1,3,5-triazacyclohepta-1,2,4,6-tetraene and ring opening to (2-Isocyanovinyl)carbodiimide.

  The Journal of organic chemistry 20021129

• Development of new amination reaction at 4-position of pyrimidine nucleosides.

  Nucleic acids research. Supplement (2001) 20020101

• Ferromagnetic exchange coupling of vanadium(IV) dpi spins across pyrimidine rings: dinuclear complexes of oxovanadium(IV) bis(1,1,1,5,5,5-hexafluoropentane-2,4-dionate) bridged by pyrimidine derivatives.

  Inorganic chemistry 20011231