Category: pyrimidines

Javaid, Z. Z. published the artcilePyrimidine nucleobase ligands of orotate phosphoribosyltransferase from Toxoplasma gondii, Synthetic Route of 19030-75-2, the main research area is orotate phosphoribosyltransferase pyrimidine nucleobase ligand Toxoplasma.

Sixty-seven pyrimidine nucleobase analogs were evaluated as ligands of Toxoplasma gondii orotate phosphoribosyltransferase (OPRTase, EC 2.4.2.10) by measuring their ability to inhibit this enzyme in vitro. Apparent Ki values were determined for compounds that inhibited T. gondii OPRTase by greater than 20% at a concentration of 400 μM. 1-Deazaorotic acid (0.47 μM) and 5-azaorotic acid (2.1 μM) were found to bind better (8.3- and 1.9-fold, resp.) to T. gondii OPRTase than orotic acid, the natural substrate of the enzyme. Based on these results, a structure-activity relationship of ligand binding to OPRTase was formulated using uracil, barbituric acid, and orotic acid as reference compounds It was concluded that the following structural features of pyrimidine nucleobase analogs were required or strongly preferred for binding: (i) an endocyclic pyridine-type nitrogen or methine at the 1-position; (ii) exocyclic oxo groups at the 2- and 4-positions; (iii) a protonated endocyclic pyridine-type nitrogen at the 3-position; (iv) an endocyclic pyridine-type nitrogen or methine at the 5-position; (v) an exocyclic hydrogen or fluorine at the 5-position; (vi) an endocyclic pyridine-type nitrogen or methine at the 6-position; and (vii) an exocyclic neg. charged or electron-withdrawing group at the 6-position. A comparison of the results from the present study with those from a previous study on mammalian OPRTase [Niedzwicki et al., Biochem Pharmacol 33: 2383-2395, 1984] identified four compounds (6-chlorouracil, 5-azaorotic acid, 1-deazaorotic acid, and 6-iodouracil) that may bind selectively to T. gondii OPRTase.

Biochemical Pharmacology published new progress about Enzyme inhibition kinetics. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Synthetic Route of 19030-75-2.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Wodynski, Artur published the artcileInterpretation of the Longitudinal 13C Nuclear Spin Relaxation and Chemical Shift Data for Five Bromoazaheterocycles Supported by Nonrelativistic and Relativistic DFT Calculations, Computed Properties of 36847-11-7, the main research area is longitudinal carbon nuclear spin relaxation chem shift bromoazaheterocycle.

The longitudinal relaxation times of 13C nuclei and NOE enhancement factors for 2-bromopyridine (1), 6-bromo-9-methylpurine (2), 3,5-dibromopyridine (3), 2,4-dibromopyrimidine (4), and 2,4,6-tribromopyrimidine (5) were measured at 25° and B0 = 11.7 T. The most important contributions to the overall relaxation rates of nonbrominated carbons, i.e., the relaxation rates due to the 13C-1H dipolar interactions and the shielding anisotropy mechanism, were separated out. For 3 and 5, addnl., the T2,q(14N) values were established from 14N NMR line widths. All of these data were used to determine rotational diffusion tensors for the studied mols. The measured saturation recovery curves of brominated carbons were decomposed into two components to yield relaxation times, which after proper corrections provided parameters characterizing the scalar relaxation of the 2nd kind for 13C nuclei of 79Br- and 81Br-bonded carbons. These parameters and theor. calculated quadrupole coupling constants for Br nuclei have allowed the values of 1-bond 13C-79Br spin-spin coupling constants to be calculated Independently, the coupling constants and magnetic shielding constants of the C nuclei were calculated theor. using the nonrelativistic and relativistic DFT methods F/6-311++G(2d,p)/PCM and so-ZORA/F/TZ2P/COSMO (F = BHandH or B3LYP), resp. The agreement between the exptl. and theor. values of these parameters is remarkably dependent on the theor. method used.

Journal of Physical Chemistry A published new progress about Magnetic relaxation (13C). 36847-11-7 belongs to class pyrimidines, name is 2,4,6-Tribromopyrimidine, and the molecular formula is C4HBr3N2, Computed Properties of 36847-11-7.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Henderson, Scott H. published the artcileDiscovery and Characterization of Selective and Ligand-Efficient DYRK Inhibitors, Name: 4-Chloro-6-isopropylpyrimidin-2-amine, the main research area is DYRK inhibitor ligand efficient.

Dual-specificity tyrosine-regulated kinase 1A (DYRK1A) regulates the proliferation and differentiation of neuronal progenitor cells during brain development. Consequently, DYRK1A has attracted interest as a target for the treatment of neurodegenerative diseases, including Alzheimer’s disease (AD) and Down’s syndrome. Recently, the inhibition of DYRK1A has been investigated as a potential treatment for diabetes, while DYRK1A’s role as a mediator in the cell cycle has garnered interest in oncol. indications. Structure-activity relationship (SAR) anal. in combination with high-resolution X-ray crystallog. leads to a series of pyrazolo[1,5-b]pyridazine inhibitors with excellent ligand efficiencies, good physicochem. properties, and a high degree of selectivity over the kinome. Compound 11 (I) exhibited good permeability and cellular activity without P-glycoprotein liability, extending the utility of 11 in an in vivo setting. These pyrazolo[1,5-b]pyridazines are a viable lead series in the discovery of new therapies for the treatment of diseases linked to DYRK1A function.

Journal of Medicinal Chemistry published new progress about Bioactive lead compounds. 73576-33-7 belongs to class pyrimidines, name is 4-Chloro-6-isopropylpyrimidin-2-amine, and the molecular formula is C7H10ClN3, Name: 4-Chloro-6-isopropylpyrimidin-2-amine.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Koroniak, Henryk published the artcileFacile large scale synthesis of 5-alkyluracils, COA of Formula: C7H10N2O2, the main research area is reduction dechlorination alkyl chlorouracil preparation; reductive dechlorination catalyst nickel aluminum alloy; alkyluracil preparation.

Cyclocondensation of alkylmalonates with urea gave alkylbarbituric acids which were treated with POCl3 to give 5-alkyl-6-chlorouracils I (R = alkyl), presumably through a 2,4,6-trichloro-5-alkylpyrimidine which is hydrolyzed. Reductive dechlorination of I with Al-Ni alloy gave the title compounds II (R = alkyl). Catalytic reduction of I with sodium borohydride was only useful for small-scale reactions.

Organic Preparations and Procedures International published new progress about Reductive dechlorination. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, COA of Formula: C7H10N2O2.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Li, Yanjun published the artcileOrganophotocatalytic selective deuterodehalogenation of aryl or alkyl chlorides, Application In Synthesis of 439692-55-4, the main research area is deuterated aryl heteroaryl compound green preparation; aryl chloride alkyl organophotocatalyst selective deuterodehalogenation.

A photocatalytic system consisting of an aryl-amine photocatalyst and a disulfide co-catalyst in the presence of sodium formate as an electron and hydrogen donor was developed. Accordingly, many aryl chlorides, alkyl chlorides, and other halides were converted to deuterated products at room temperature in air (>90 examples, up to 99% D-incorporation). The mechanistic studies revealed that the aryl amine served as reducing photoredox catalyst to initiate cleavage of the C-Cl bond, at the same time as energy transfer catalyst to induce homolysis of the disulfide for consequent deuterium transfer process. This economic and environmentally-friendly method could be used for site-selective D-labeling of a number of bioactive mols. and direct H/D exchange of some drug mols.

Nature Communications published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 439692-55-4 belongs to class pyrimidines, name is Thieno[2,3-d]pyrimidine, 4-chloro-6-(1,1-dimethylethyl)-, and the molecular formula is C10H11ClN2S, Application In Synthesis of 439692-55-4.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Wei, Xiao-Jing published the artcileVisible-Light-Promoted Iron-Catalyzed C(sp2)-C(sp3) Kumada Cross-Coupling in Flow, Formula: C5H5ClN2S, the main research area is Kumada cross coupling aryl chloride Grignard reagent iron catalyst; visible light Kumada cross coupling iron catalyst mechanism flow; Kumada coupling; cross-coupling; flow chemistry; iron catalysis; photocatalysis.

A continuous-flow, visible-light-promoted method has been developed to overcome the limitations of iron-catalyzed Kumada-Corriu cross-coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability of this iron-catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application. The mechanism was studied using radical clock experiments, kinetic measurements, DFT and other techniques.

Angewandte Chemie, International Edition published new progress about Aryl chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 38275-42-2 belongs to class pyrimidines, name is 5-Chloro-2-(methylthio)pyrimidine, and the molecular formula is C5H5ClN2S, Formula: C5H5ClN2S.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Klumpp, Douglas A. published the artcileElectrophilic activation of acetyl-substituted heteroaromatic compounds, Computed Properties of 66373-25-9, the main research area is electrophilic activation condensation benzene heteroaromatic compound; superacid mediated condensation heteroaromatic methyl ketone benzene.

The chem. of acetyl-substituted pyridines, thiazoles, quinoline, isoquinolines, and pyrazine, e.g., thiazole I, has been studied. These heteroarenes condense with benzene in good yields (74-96%) in the Bronsted superacid, CF3SO3H (triflic acid). Thus, reaction of I gave diphenylthiazole II in 91% yield. In these acid-catalyzed hydroxyalkylation reactions, the heteroarene compounds are significantly more reactive than acetophenone. It is proposed that the heteroarene compounds readily form dicationic electrophiles in triflic acid.

Journal of Organic Chemistry published new progress about Aryl ketones Role: RCT (Reactant), RACT (Reactant or Reagent). 66373-25-9 belongs to class pyrimidines, name is 1-(2-Amino-4-methylpyrimidin-5-yl)ethanone, and the molecular formula is C7H9N3O, Computed Properties of 66373-25-9.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Brumfield, Martha A. published the artcileTwo triplets mediating intramolecular photochemical abstraction of hydrogen by nitrogen in 4-acyl-6-alkylpyrimidines, Recommanded Product: 1-(6-Methylpyrimidin-4-yl)ethanone, the main research area is photocyclization acylalkylpyrimidine; intramol photochem hydrogen abstraction acylalkylpyrimidine; triplet state hydrogen abstraction acylaklylpyrimidine; pyrimidine acylalkyl triplet photochem.

Direct irradiation with λ >340 nm of 4-acyl-6-alkylpyrimidines I (R = Me) and II (R = CH2CH2CHMe2) or their triplet sensitization by aromatic ketones leads to an nπ* triplet (ET ∼70-71 kcal/mol). In I (R = Me) this state is responsible for hydrogen abstraction from the C(4) side chain and isomerization to cyclopropanol III. Ketone II (R = CH2CH2CHMe2) does not fragment under either of these direct or sensitized conditions. However, triplet sensitization of II (R = CH2CH2CHMe2) by acetone (ET ∼79-82 kcal/mol) or direct irradiation of II (R = CH2CH2CHMe2) through Vycor, λ > 200 nm, leads to hydrogen abstraction, cleavage of the C(6) side chain, and formation of II (R = Me) in a reaction occurring from an upper nπ* triplet (ET ∼79-84 kcal/mol). Ketone I (R = CH2CH2CHMe2) yields mainly IV and, depending upon conditions, a small amount of I (R = Me) or III; the minor products arise by a novel monophotonic pathway.

Journal of the American Chemical Society published new progress about Photoabstraction reaction, intramolecular photoabstraction. 67073-96-5 belongs to class pyrimidines, name is 1-(6-Methylpyrimidin-4-yl)ethanone, and the molecular formula is C7H8N2O, Recommanded Product: 1-(6-Methylpyrimidin-4-yl)ethanone.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

White, James D. published the artcileTotal Synthesis of (-)-7-Epicylindrospermopsin, a Toxic Metabolite of the Freshwater Cyanobacterium Aphanizomenon ovalisporum, and Assignment of Its Absolute Configuration, Computed Properties of 36847-11-7, the main research area is epicylindrospermopsin total synthesis absolute configuration.

The Z and E nitrones II, prepared from condensation of the corresponding aldehyde and hydroxylamine, underwent intramol. dipolar cycloaddition to give substituted 1-aza-7-oxobicyclo[2.2.1] heptanes. Reductive N-O bond cleavage followed by carbonylation gave the cyclic urea in which inversion of the secondary alc. was effected via an oxidation-reduction sequence. After conversion of the p-bromobenzyl ether to the azide, activation of the cyclic urea as its O-methylisourea and reduction of the azide led to spontaneous cyclization to afford the tricyclic nucleus of cylindrospermopsin. Global deprotection, including hydrolysis of the 2,4-dimethoxypyrimidine appendage to a uracil, and then monosulfation of the resultant diol afforded a substance identical with natural (-)-7-epicylindrospermopsin (I). The asym. synthesis of (-)-7-epicylindrospermopsin defines its absolute configuration as 7S,8R,10S,12S,13R,14S.

Journal of Organic Chemistry published new progress about 1,3-Dipolar cycloaddition reaction, stereoselective. 36847-11-7 belongs to class pyrimidines, name is 2,4,6-Tribromopyrimidine, and the molecular formula is C4HBr3N2, Computed Properties of 36847-11-7.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Looper, Ryan E. published the artcileSyntheses of the cylindrospermopsin alkaloids, HPLC of Formula: 36847-11-7, the main research area is cylindrospermopsin alkaloid asym synthesis intramol dipolar cycloaddition; nitro aldol addition cylindrospermopsin alkaloid asym synthesis; reductive guanidinylation cylindrospermopsin alkaloid asym synthesis.

An intramol. 1,3-dipolar cycloaddition has efficiently constructed the A-ring portions of the cylindrospermopsin alkaloids. A nitro-aldol addition of an elaborated nitroalkane to a pyrimidine aldehyde followed by an intramol. reductive guanidinylation has enabled the syntheses of all three alkaloids in this family in 18-19 steps. The first asym. synthesis of cylindrospermopsin (I), unambiguously assigning its absolute configuration, was reported.

Tetrahedron published new progress about 1,3-Dipolar cycloaddition reaction, intramolecular. 36847-11-7 belongs to class pyrimidines, name is 2,4,6-Tribromopyrimidine, and the molecular formula is C4HBr3N2, HPLC of Formula: 36847-11-7.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia