Category: 19030-75-2

Kulikowski, Tadeusz published the artcile5-Substituted arabinofuranosyluracil nucleosides: synthesis and antiviral properties, Recommanded Product: 5-N-Propyluracil, the main research area is arabinofuranosyluracil nucleoside preparation virucide; alkyluracil arabinofuranosyl; structure antiviral activity arabinofuranosyluracil.

The title nucleosides I (R = Et, Pr, Me2CH, Bu), their α-anomers and N-3 isomers were prepared by a number of different procedures based on the catalytic condensation of the corresponding 5-alkyl-2,4-bis(trimethylsilyloxy)pyrimidines with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride. The resulting protected nucleosides were deblocked by a new procedure based on the use of BF3.Et2O and EtSH. The chloromercuri derivative of ara-U (I; R = H) on reaction with allyl chloride in the presence of Li2PdCl4 gave I (R = allyl), which on catalytic hydrogenation gave I (R = Pr). The antiviral activities of these compounds were evaluated. I (R = allyl) showed moderate specific activity against herpes simplex type 1 virus in PRK cell culture. Structure-activity relationships are discussed.

Acta Biochimica Polonica published new progress about Antiviral agents. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Recommanded Product: 5-N-Propyluracil.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Nakayama, Chikao published the artcileSynthetic nucleosides and nucleotides. XII. Synthesis and antiviral activities of several 1-β-D-arabinofuranosyl-5-alkyluracils and their 5′-monophosphates, HPLC of Formula: 19030-75-2, the main research area is arabinofuranosylalkyluracil preparation virucide; nucleoside arabinofuranosylalkyluracil; nucleotide arabinofuranosylalkyluracil; uracil arabinofuranosylalkyl.

Arabinofuranosyluracils I (R = Me, Et, Pr, Bu) were prepared by acid hydrolysis of anhydronucleosides II. II were prepared from pyrimidines III by 2 routes : (a) condensation with 1,2-di-O-acetyl-3-O-p-toluenesulfonyl-5-O-benzoyl-D-xylofuranose and treatment of the products with MeONa-MeOH; (b) condensation with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose followed by debenzoylation and cyclization. Phosphorylation of I (R = Me, Et) or II (R = Me, Et) with tetrachloropyrophosphate in MeCn followed by treatment with acid gave 1-β-D-arabinofuranosyl-5-alkyluracil 5′-phosphates (IV). Antiviral activities of I, II, and IV against herpes simplex 1 and 2 are given; I (R = Me) and IV (R = Me) were significantly active against both the viruses.

Journal of Carbohydrates, Nucleosides, Nucleotides published new progress about Antiviral agents. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, HPLC of Formula: 19030-75-2.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Rode, W. published the artcileInhibition of mammalian tumor thymidylate synthetase by 5-alkylated 2′-deoxyuridine 5′-phosphates, Related Products of pyrimidines, the main research area is alkylated deoxyuridine phosphate tumor; thymidylate synthetase inhibition tumor.

Improved syntheses, based on Lewis acid-catalyzed nucleosidation, are described for the preparation of 5-alkyl-2′-deoxyuridines. These were converted to their 5′-phosphates with the use of wheat shoot phosphotransferase. The dUMP analogs 5-ethyl-dUMP  [56576-83-1] and 5-propyl-dUMP  [64374-82-9] were competitive vs. dUMP inhibitors of thymidylate synthetase  [9031-61-2] purified from mouse L1210, Ehrlich ascites, and HeLa cells, the former being the stronger inhibitor. Both analogs bind cooperatively to each of the mouse tumor enzymes, 2 mols. of inhibitor interacting with a single enzyme mol., as reflected by the parabolic character of the replots of the slope vs. inhibitor concentrations DTMP  [365-07-1] was a stronger inhibitor of the mouse tumor enzymes than its higher alkyl homologs.

Biochemical Pharmacology published new progress about Antitumor agents. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Related Products of pyrimidines.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Knoblauch, Bernd H. A. published the artcile5-substituted UTP derivatives as P2Y2 receptor agonists, Product Details of C7H10N2O2, the main research area is UTP analog preparation phosphorylation structure activity; uracil nucleotide crystal structure; purinergic P2Y2 receptor antagonist uracil nucleotide.

A series of 5-alkyl-substituted UTP derivatives, which had been synthesized previously with a moderate degree of purity, was resynthesized, purified, and characterized. Synthetic and purification procedures were optimized. New spectroscopic data, including 13C- and 31P NMR data, are presented. Phosphorylation reactions yielded a number of side products, such as the 2′-, 3′-, and 5′-monophosphates, the 2′,3′-cyclic monophosphates, and the 2′,3′-cyclic phosphates of the 5′-triphosphates. Furthermore, raw products were contaminated with inorganic phosphates, including cyclometatriphosphate, phosphate, and pyrophosphate. The uracil nucleotides were investigated for their potency to increase intracellular calcium concentrations by stimulation of P2Y2 receptors (P2Y2R) on NG108-15 cells, a mouse neuroblastoma × glioma cell line, and in human basal epithelial airway cells, including a cystic fibrosis (CF/T43) cell line. UTP exhibited EC50 values of ca. 1 μM (in NG108-15 cells) and of 0.1 μM (in CF/T43 cells), resp. 5-Substituted UTP derivatives were agonists at the P2Y2R, but were less potent than UTP. 5-Ethyl-UTP, for example, exhibited an EC50 value of 99 μM at P2Y2R of NG108-15 cells and proved to be a full agonist. With increasing volume of the 5-substituent of UTP derivatives, P2Y2 activity decreased.

European Journal of Medicinal Chemistry published new progress about Crystal structure. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Product Details of C7H10N2O2.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Henriksen, Ulla published the artcileFacile synthesis of N-(1-alkenyl) derivatives of 2,4-pyrimidinediones, Application In Synthesis of 19030-75-2, the main research area is pyrimidinedione alkenyl derivative synthesis.

N-(1-alkenyl) derivatives of 2,4-pyrimidinediones were prepared in a one pot synthesis from aldehydes and the nucleobases using trimethylsilyl trifluoromethanesulfonate (TfOTMS) as coupling reagent. Presilylation of the above nucleobases, and N6-benzoyladenine, with excess N,O-bis(trimethylsilyl)acetamide (BSA) followed by addition of one mol eq. TfOTMS yielded the N-(1-trimethylsilyloxyalkyl) derivatives

Nucleosides, Nucleotides & Nucleic Acids published new progress about Coupling reaction. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Application In Synthesis of 19030-75-2.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Uddin, Kabir M. published the artcileNew insight into the substituent effects on the hydrolytic deamination of saturated and unsaturated cytosine, Related Products of pyrimidines, the main research area is cytosine hydrolytic deamination substituent effect thermodn property.

Ab initio calculations were carried out to understand the effect of electron donating groups (EDG) and electron withdrawing groups (EWG) at the C5 position of cytosine (Cyt) and saturated cytosine (H2Cyt) of the deamination reaction. Geometries of the reactants, transition states, intermediates, and products were fully optimized at the B3LYP/6-31G(d,p) level in the gas phase as this level of theory has been found to agree very well with G3 theories. Activation energies, enthalpies, and Gibbs energies of activation along with the thermodn. properties (ΔE, ΔH, and ΔG) of each reaction were calculated A plot of the Gibbs energies of activation (ΔG ) for C5 substituted Cyt and H2Cyt against the Hammett σ-constants reveal a good linear relationship. In general, both EDG and EWG substituents at the C5 position in Cyt results in higher ΔG and lower σ values compared to those of H2Cyt deamination reactions. C5 alkyl substituents (H, CH3, CH2CH3, CH2CH2CH3) increase ΔG values for Cyt, while the same substituents decrease ΔG values for H2Cyt which is likely due to steric effects. However, the Hammett σ-constants were found to decrease at the C5 position of cytosine (Cyt) and saturated cytosine (H2Cyt) on the deamination reaction. Both ΔG and σ values decrease for the substituents Cl and Br in the Cyt reaction, while ΔG values increase and σ decrease in the H2Cyt reaction. This may be due to high polarizability of bromine which results in a greater stabilization of the transition state in the case of bromine compared to chlorine. Regardless of the substituent at C5, the pos. charge on C4 is greater in the TS compared to the reactant complex for both the Cyt and H2Cyt. Moreover, as the charges on C4 in the TS increase compared to reactant, ΔG also increase for the C5 alkyl substituents (H, CH3, CH2CH3, CH2CH2CH3) in Cyt, while ΔG decrease in H2Cyt. In addition, anal. of the frontier MO energies for the transition state structures shows that there is a correlation between the energy of the HOMO-LUMO gap and activation energies.

International Journal of Quantum Chemistry published new progress about Activation energy. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Related Products of pyrimidines.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Basnak, Ivan published the artcileNucleic acid components and their analogs. CXCVIII. Synthesis of uracils substituted in the position 5 or 5,6 with alkyl or cycloalkyl groups and their UV spectra, Application In Synthesis of 19030-75-2, the main research area is thiouracil oxidation; uracil cycloalkyl; Claisen condensation formate acetate; catalyst Claisen condensation; cyclization oxoalkanoate thiourea.

Li diazopropylamide, used as a base in the Claisen condensation of alkylacetates and cycloalkylacetates with EtO2CH or EtOAc gave higher yields of β-oxo esters than NaH or NaN(SiMe2)2. Cyclization of the obtained β-oxo esters with thiourea in an alk. medium gave thiouracils I (X = S), which on subsequent reaction with ClCH2CO2H were transformed into uracils I (X = O, R1 = Me, Me2CH, cyclopropyl, cyclobutyl, cyclopentyl, Pr, Me3C; R2 = Me, Me2CH, Me2CHCH2, cyclopropylmethyl, cyclopropyl).

Collection of Czechoslovak Chemical Communications published new progress about Claisen condensation. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Application In Synthesis of 19030-75-2.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Strop, P. published the artcileSeparation of alkyl derivatives of uracil by solvophobic adsorption chromatography on Spheron, Safety of 5-N-Propyluracil, the main research area is uracil derivative chromatog; pyrimidine derivative chromatog.

Derivatives of such related substances as cytosine, uracil, thymine, 6-methyluracil, 5-ethyluracil, 5-propyluracil, 5-isopropyluracil, 5-cyclopropyluracil, 5-allyluracil, 5,6-trimethyleneuracil, 6-cyclopropyluracil, 5-cyclobutyluracil and 5-tert-butyluracil were separated on a column of Spheron P-300. Retention on the column was found to depend on the size of the nonpolar part of the mol. The chromatog. behavior was analyzed according to the theory of solvophobic chromatog.

Journal of Chromatography published new progress about Liquid chromatography. 19030-75-2 belongs to class pyrimidines, name is 5-N-Propyluracil, and the molecular formula is C7H10N2O2, Safety of 5-N-Propyluracil.

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

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