Category: 608-34-4

Shih, Phoebe published the artcileHydrophobicities of the nucleic acid bases: distribution coefficients from water to cyclohexane, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of Molecular Biology (1998), 280(3), 421-430, database is CAplus and MEDLINE.

To establish an exptl. scale of hydrophobicities for the nucleic acid bases, comparable with a scale developed earlier for amino acid side-chains, these bases and their parent compounds (purine and pyrimidin-2-one) were converted to n-butylated and tetrahydrofurylated derivatives that are appreciably soluble in cyclohexane, a truly non-polar solvent that dissolves negligible water at saturation Distribution measurements between neutral aqueous solution and cyclohexane, at varying solute concentrations, showed no evidence of self-association of the solute in either solvent, and the possibility of specific entrainment of water by solutes entering cyclohexane was ruled out by the results of experiments with tritiated water. In both the Bu and tetrahydrofuryl series, the bases span a range of �.3 kcal mol^-1 in their free energies of transfer from water to cyclohexane, and are arranged in the following rank, in order of decreasing hydrophobicity: purine > thymine > adenine > uracil > pyrimidin-2-one > hypoxanthine �cytosine �guanine. In both series of pyrimidin-2-ones, hydrophobicity decreases with introduction of an amino substituent, but addition of an exocyclic keto group results in a modest enhancement of hydrophobicity; and free energies of transfer are relatively insensitive to the position of N-alkyl substitution. In both series of purines, hydrophobicity decreases with the introduction of exocyclic amino and keto groups, the keto group having the greater effect; and free energies of transfer vary substantially depending on the position of N-alkyl substitution. Several addnl. compounds were examined to test recent predictions based on SM5.4/A, a quantum mech. self-consistent-field solvation model; and that model was found to yield values in reasonable agreement with the exptl. results. (c) 1998 Academic Press.

Journal of Molecular Biology published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C27H39ClN2, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Pizzirani, Daniela published the artcileDiscovery of a New Class of Highly Potent Inhibitors of Acid Ceramidase: Synthesis and Structure-Activity Relationship (SAR), Product Details of C5H6N2O2, the publication is Journal of Medicinal Chemistry (2013), 56(9), 3518-3530, database is CAplus and MEDLINE.

1-(Alkylamino)-2,4-pyrimidinediones such as I [R = H, F, MeO, F₃C, Ph; R¹ = Me(CH₂)_nNH; R² = H, Me, MeO₂C; n = 5, 7] were prepared as inhibitors of acid ceramidase for potential use as antitumor agents. Uracils bearing an electron-withdrawing substituent at position 5, a substituent such as Me at position 3, and an alkylaminocarbonyl moiety with a six- to eight-carbon alkyl group at position 1 were the most effective inhibitors of acid ceramidase of the compounds tested. The acid ceramidase inhibition and stability of an alkylaminopyrimidinedione was correlated with the stabilization of the antibonding orbital of its N1-carbonyl bond. I (R = H, F, Ph; R² = H, Me; n = 5, 7) inhibited a human cancer cell line (SW403) with IC₅₀ values of 20-24 μM. I (R = F, F₃C, MeO; R² = H, MeO₂C; n = 5, 7) inhibited acid ceramidase with single digit-nanomolar IC₅₀ values (IC₅₀ = 4-7 nM).

Journal of Medicinal Chemistry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Product Details of C5H6N2O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Sulkowska, A. published the artcileProton NMR studies on the interaction of alkyl derivatives of pyrimidine bases, their nucleosides and nucleotides with bovine serum albumin, Product Details of C5H6N2O2, the publication is Journal of Molecular Structure (1995), 73-6, database is CAplus.

Besides well known structural units rare purine and pyrimidine bases are found in some nucleic acids. Most of them are Me derivatives of the major bases, but some contain acetyl, isopentenyl, or hydroxymethyl groups. Rare bases are especially prominent in tRNAs which characteristically contain up to 10 percent of these unusual components. The aim of this study was to provide by ¹H NMR spectroscopy a detailed exptl. base for understanding the nature of hydrophobic complexes formed by pyrimidine bases, their nucleosides and nucleotides when they interact with protein. As the model protein bovine serum albumin (BSA) has been selected. Addition of serum albumin caused a broadening of the NMR signals.

Journal of Molecular Structure published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C6H9N3O2, Product Details of C5H6N2O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Ferreira da Silva, Filipe published the artcileNCO^–, a Key Fragment Upon Dissociative Electron Attachment and Electron Transfer to Pyrimidine Bases: Site Selectivity for a Slow Decay Process, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of the American Society for Mass Spectrometry (2013), 24(11), 1787-1797, database is CAplus and MEDLINE.

We report gas phase studies on NCO^– fragment formation from the nucleobases thymine and uracil and their N-site methylated derivatives upon dissociative electron attachment (DEA) and through electron transfer in potassium collisions. For comparison, the NCO^– production in metastable decay of the nucleobases after deprotonation in matrix assisted laser desorption/ionization (MALDI) is also reported. We show that the delayed fragmentation of the dehydrogenated closed-shell anion into NCO^– upon DEA proceeds few microseconds after the electron attachment process, indicating a rather slow unimol. decomposition Utilizing partially methylated thymine, we demonstrate that the remarkable site selectivity of the initial hydrogen loss as a function of the electron energy is preserved in the prompt as well as the metastable NCO^– formation in DEA. Site selectivity in the NCO^– yield is also pronounced after deprotonation in MALDI, though distinctly different from that observed in DEA. This is discussed in terms of the different electronic states subjected to metastable decay in these experiments In potassium collisions with 1- and 3-methylthymine and 1- and 3-methyluracil, the dominant fragment is the NCO^– ion and the branching ratios as a function of the collision energy show evidence of extraordinary site-selectivity in the reactions yielding its formation.

Journal of the American Society for Mass Spectrometry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Almeida, D. published the artcileDemethylation enhancement of 3-methyl-uracil and 1-methyl-thymine in atom-molecule collisions, Computed Properties of 608-34-4, the publication is Journal of Physics: Conference Series (2012), 388(Part 10), 102031/1, database is CAplus.

The authors report the formation of demethylation in 3-methyl-uracil (3meU) and 1-methyl-thymine (1meT), i.e. (3meU-CH3)- and (1meT-CH3)-, through potassium-mol. collisions at different potassium kinetic energies. Study of the threshold of formation of this fragment can provide a value of threshold energy that can be compared with DEA studies.

Journal of Physics: Conference Series published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Computed Properties of 608-34-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Etinski, Mihajlo published the artcileAb initio investigation of the methylation and hydration effects on the electronic spectra of uracil and thymine, Product Details of C5H6N2O2, the publication is Physical Chemistry Chemical Physics (2010), 12(19), 4915-4923, database is CAplus and MEDLINE.

In this work, we investigated the lowest-lying electronic excitations for a series of methyl-substituted uracil derivatives, i.e., uracil, 1-methyluracil, 3-methyluracil, thymine, 1-methylthymine, 1,3-dimethyluracil, 3-methylthymine, 1,3-dimethylthymine, and their microhydrated complexes by means of coupled cluster singles and approx. doubles (CC2) and d. functional theory (DFT) methods. The bulk water environment was mimicked by a combination of microhydration and the conductor-like screening model (COSMO). We find that the shift of the electronic excitation energies due to methylation and hydration depend on the character of the wave function and on the position of the Me substituent. The lowest-lying singlet and triplet n → π^* states are insensitive to methylation but are strongly blue-shifted by microhydration and bulk water solvation. The largest red-shift of the first ¹(π → π^*) excitation occurs upon methylation at N₁ followed by substitution at C₅ whereas no effect is obtained for a methylation at N₃. For this state, the effects of methylation and hydrogen bonding partially cancel. Upon microhydration with six water mols., the order of the ¹(n → π^*) and ¹(π → π^*) states is reversed in the vertical spectrum. Electrostatic solute-solvent interaction in bulk water leads to a further increase of their energy separation The n → π^* states are important intermediates for the triplet formation. Shifting them energetically above the primarily excited ¹(π → π^*) state will considerably decrease the triplet quantum yield and thus increase the photostability of the compounds, in agreement with exptl. observations.

Physical Chemistry Chemical Physics published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Product Details of C5H6N2O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Huang, Xian published the artcileSolid-Phase Synthesis of 4(1H)-Quinolone and Pyrimidine Derivatives Based on a New Scaffold-Polymer-Bound Cyclic Malonic Acid Ester, Computed Properties of 608-34-4, the publication is Journal of Organic Chemistry (2002), 67(19), 6731-6737, database is CAplus and MEDLINE.

An efficient method for the preparation of polymer-bound cyclic malonic acid ester starting from Merrifield resin has been developed. Reaction of the resin-bound cyclic malonic acid ester with tri-Et orthoformate and subsequent double substitution with nucleophilic reagents, such as arylamine, urea, thiourea, 2-aminobenzothiazoles, or isothiosemicarbazones, afforded the corresponding polymer-bound substituted aminomethylene cyclic malonic acid esters, which upon thermal treatment led to 4(1H)-quinolones, 3-substituted uracils and thiouracils, 4H-pyrimido[2,1-b]benzothiazol-4-ones, and 1-(N-alkylidene or benzylideneamino)-1,6-dihydro-2-methylthio-6-oxo-pyrimidines, depending on the structures of the nucleophilic reagents.

Journal of Organic Chemistry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Computed Properties of 608-34-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Qiu, Bo published the artcileQuintets of uracil and thymine: a novel structure of nucleobase self-assembly studied by electrospray ionization mass spectrometry, Name: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Chemical Communications (Cambridge, United Kingdom) (2009), 2863-2865, database is CAplus and MEDLINE.

ESI-MS and mol. dynamic calculations reveal that in the presence of K⁺, Rb⁺ and Cs⁺, uracil, thymine and their homologs form self-assembled quintet structures that are stabilized by hydrogen bonding and ion dipole interactions.

Chemical Communications (Cambridge, United Kingdom) published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Name: 3-Methylpyrimidine-2,4(1H,3H)-dione.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Lemoine, Remy C. published the artcileSynthesis of base-modified dihydropacidamycins, Application In Synthesis of 608-34-4, the publication is Bioorganic & Medicinal Chemistry Letters (2002), 12(7), 1121-1123, database is CAplus and MEDLINE.

The authors describe the synthesis of 1,2-di-O-acetyl-5-azido-3,5-dideoxy-α,β-L-arabinofuranose, a carbohydrate donor that was used for the synthesis of 1-(5′-amino-3′,5′-dideoxy-α-L-arabinofuranosyl)uracil, the nucleoside found in dihydropacidamycin D. The carbohydrate donor was also used for the synthesis of a set of new nucleosides that were introduced in new dihydropacidamycins. These compounds were tested for biol. activity, and the results showed that uracil is the only base recognized by MraY.

Bioorganic & Medicinal Chemistry Letters published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Application In Synthesis of 608-34-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Zhachkina, Anna published the artcileUracil and Thymine Reactivity in the Gas Phase: The S_N2 Reaction and Implications for Electron Delocalization in Leaving Groups, SDS of cas: 608-34-4, the publication is Journal of the American Chemical Society (2009), 131(51), 18376-18385, database is CAplus and MEDLINE.

The gas-phase substitution reactions of Me chloride and 1,3-dimethyluracil (at the N1-CH₃) are examined computationally and exptl. It is found that, although hydrochloric acid and 3-methyluracil are similar in acidity, the leaving group abilities of chloride and N1-deprotonated 3-methyluracil are not: chloride is a slightly better leaving group. The reason for this difference is most likely related to the electron delocalization in the N1-deprotonated 3-methyluracil anion, which we explore further herein. The leaving group ability of the N1-deprotonated 3-methyluracil anion relative to the N1-deprotonated 3-methylthymine anion is also examined in the context of an enzymic reaction that cleaves uracil but not thymine from DNA.

Journal of the American Chemical Society published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H5ClO2, SDS of cas: 608-34-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia