Category: 608-34-4

Qiu, Yan published the artcileDiscovery of uracil derivatives as potent inhibitors of fatty acid amide hydrolase, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Molecules (2016), 21(2), 229/1-229/11, database is CAplus and MEDLINE.

Fatty Acid Amide Hydrolase (FAAH) is an intracellular serine enzyme involved in the biol. degradation of the fatty acid ethanolamide family of signaling lipids, which exerts neuroprotective, anti-inflammatory, and analgesic properties. In the present study, a conjugated 2,4-dioxo-pyrimidine-1-carboxamide scaffold was confirmed as a novel template for FAAH inhibitors, based on which, a series of analogs had been prepared for an initial structure-activity relationship (SAR) study. Most of the synthesized compounds displayed moderate to significant FAAH inhibitory potency. Among them, compounds 11 and 14 showed better activity than others, with IC₅₀ values of 21 and 53 nM. SAR anal. indicated that 2,4-dioxopyrimidine-1-carboxamides represented a novel class of potent inhibitors of FAAH, and substitution at the uracil ring or replacement of the N-terminal group might favor the inhibitory potency. Selected compounds of this class may be used as useful parent mols. for further investigation.

Molecules 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 of 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Dolgounitcheva, O. published the artcileIonization Energies and Dyson Orbitals of Thymine and Other Methylated Uracils, Quality Control of 608-34-4, the publication is Journal of Physical Chemistry A (2002), 106(36), 8411-8416, database is CAplus.

Electron propagator methods are applied to the calculation of photoelectron spectra of thymine and other C- and N-methylated uracils. The Partial Third-Order electron propagator method is used. Excellent agreement with existing exptl. spectra is achieved. Relationships between reductions in ionization energies and antibonding contributions from Me groups in corresponding Dyson orbitals are discussed.

Journal of Physical Chemistry A 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, Quality Control of 608-34-4.

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

Zheltovsky, N. V. published the artcileInteractions of methyl and glycosyl derivatives of pyrimidine nucleotide bases with amino acid carboxylic group, Synthetic Route of 608-34-4, the publication is Biopolimery i Kletka (1994), 10(6), 45-51, database is CAplus.

By UV, IR, and NMR interactions of a number of Me and glycosyl derivatives of pyrimidine bases with amino acid carboxylic group in DMSO were studied as a model of probable point contacts in real nucleoprotein complexes. It was found that like the unsubstituted base 1-methylcytosine, 5-methylcytosine, 1,5-dimethylcytosine, cytidine, deoxycytidine, 5-methyldeoxycytidine form complexes with a neutral carboxylic group, and 3-methylcytosine and isocytosine interact with deprotonated carboxylic group (carboxylate ion). Like free thymine and uracil, their derivatives 1-methylthymine, 1-methyluracil, 3-methyluracil, thymidine, uridine, 5-methyluridine, deoxyuridine interact only with carboxylate ion. Anal. of the results obtained and the data of previous works points out the ability of amino acid carboxylic group to differentiate between cytosine and thymine (uracil), and between their nucleosides and derivatives as well.

Biopolimery i Kletka 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 C2H3N3, Synthetic Route of 608-34-4.

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

Zielenkiewicz, W. published the artcilePartial molar volumes of alkylated uracils- insight into the solvation shell? Part II, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of Solution Chemistry (1998), 27(6), 543-551, database is CAplus.

The solute-solvent interactions in aqueous solutions of alkylated uracils are discussed. The partial molar volume data are interpreted using a new model of interaction of the solute mol. with the solvent. The model is based on the assumption that the d. of solvent in the hydration shell depends on the structure and polarity of the solute mol. The relation among mol. volume, partial molar volume, and volume of the solvation shell is expressed by α parameter, which is defined as the relative d. of the solvation shell. It is found that in compounds with the same number of CH₂– groups, the α values depend on substitution on the C or N atoms of the uracil skeleton. The α values also depend to some extent, on screening of the oxygen atoms by methylation of the neighboring atoms of the uracil ring. A correlation is presented between the relative d. of solvation shell and polarity (defined as the ratio of the surface of polar groups and atoms exposed to the solvent to the total accessible mol. surface of the mol.) for the compounds studied. It was demonstrated that of the various solute-solvent interactions the dominant role is played by polar interactions.

Journal of Solution 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 C5H7BO2S, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Yang, Zhibo published the artcileInfluence of methylation on the properties of uracil and its noncovalent interactions with alkali metal ions. Threshold collision-induced dissociation and theoretical studies, Application In Synthesis of 608-34-4, the publication is International Journal of Mass Spectrometry (2005), 241(2-3), 225-242, database is CAplus.

The influence of methylation on the properties of uracil and its noncovalent interactions with alkali metal ions is investigated both exptl. and theor. Threshold collision-induced dissociation (CID) of M⁺(xMeU) with Xe is studied in a guided ion beam mass spectrometer. M⁺ include the following alkali metal ions: Li⁺, Na⁺, and K⁺. Five methylated uracils are examined, xMeU = 1-methyluracil, 3-methyluracil, 6-methyluracil, 1,3-dimethyluracil, and 5,6-dimethyluracil. In all cases endothermic loss of the intact nucleobase is the dominant reaction pathway, while ligand exchange to produce MXe⁺ is observed as a minor reaction pathway. The threshold regions of the cross sections are interpreted to extract 0 and 298 K bond dissociation energies (BDEs) for M⁺-xMeU after accounting for the effects of multiple ion-neutral collisions, kinetic and internal energies of the reactants, and dissociation lifetimes. Ab initio calculations at the MP2(full)/6-31G* level of theory are used to determine the structures of these complexes and provide mol. constants required for the thermochem. anal. of the exptl. data. Theor. bond dissociation energies are determined from single point energy calculations at the MP2(full)/6-211+G(2d,2p) level using the MP2(full)/6-31G* geometries. Excellent agreement between theory and experiment is found for the Na⁺ and K⁺ systems, while theory systematically underestimates the strength of binding in the Li⁺ systems. Theor. calculations are also performed to examine the influence of methylation on the acidities, proton affinities, and Watson-Crick base pairing energies. The present results are compared to earlier studies of uracil and 5-methyluracil to more fully elucidate the influence of methylation on the properties of uracil, its noncovalent interactions with alkali metal ions, and nucleic acid stability.

International Journal of 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 C20H40O2, Application In Synthesis of 608-34-4.

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

Qiu, Yan published the artcileDesign and synthesis of uracil urea derivatives as potent and selective fatty acid amide hydrolase inhibitors, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is RSC Advances (2017), 7(37), 22699-22705, database is CAplus.

Fatty acid amide hydrolase (FAAH) is one of the key enzymes involved in the biol. degradation of endocannabinoids, especially anandamide. Pharmacol. blockage of FAAH restores the levels of endocannabinoids, providing therapeutic benefits in the management of inflammation, depression and multiple sclerosis. In this study, a series of uracil urea derivatives as FAAH inhibitors were designed and synthesized. Structural modifications at the C5 position and side chain of N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide (1a) led to FAAH inhibitors with improved potency and selectivity. Structure-activity relationship (SAR) studies indicated that C5 electron-withdrawing substituents were preferred for optimal potency but not for selectivity, whereas replacement of the alkyl chain with phenylalkyl moieties or biphenyl groups significantly improved both inhibitory potency and selectivity towards FAAH. Two highly potent picomolar FAAH inhibitors (4c, IC₅₀ = 0.3 ± 0.05 nM; 4d, IC₅₀ = 0.8 ± 0.1 nM) were developed. Compound 4c inhibited FAAH in a rapid, selective, noncompetitive, and irreversible pattern. This study provides several highly potent and selective FAAH inhibitors and an optimized chem. scaffold for the development of FAAH inhibitors. We anticipate that these FAAH inhibitors will enable new possibilities in understanding FAAH functions and development of therapeutics for pain and inflammatory diseases.

RSC Advances 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

Marcinkowski, Michal published the artcileEffect of posttranslational modifications on the structure and activity of FTO demethylase, Formula: C5H6N2O2, the publication is International Journal of Molecular Sciences (2021), 22(9), 4512, database is CAplus and MEDLINE.

The FTO protein is involved in a wide range of physiol. processes, including adipogenesis and osteogenesis. This two-domain protein belongs to the AlkB family of 2-oxoglutarate (2-OG)- and Fe(II)-dependent dioxygenases, displaying N6-methyladenosine (N6-meA) demethylase activity. The aim of the study was to characterize the relationships between the structure and activity of FTO. The effect of cofactors (Fe²⁺/Mn²⁺ and 2-OG), Ca²⁺ that do not bind at the catalytic site, and protein concentration on FTO properties expressed in either E. coli (ECFTO) or baculovirus (BESFTO) system were determined using biophys. methods (DSF, MST, SAXS) and biochem. techniques (size-exclusion chromatog., enzymic assay). We found that BESFTO carries three phosphoserines (S184, S256, S260), while there were no such modifications in ECFTO. The S256D mutation mimicking the S256 phosphorylation moderately decreased FTO catalytic activity. In the presence of Ca²⁺, a slight stabilization of the FTO structure was observed, accompanied by a decrease in catalytic activity. Size exclusion chromatog. and MST data confirmed the ability of FTO from both expression systems to form homodimers. The MST-determined dissociation constant of the FTO homodimer was consistent with their in vivo formation in human cells. Finally, a low-resolution structure of the FTO homodimer was built based on SAXS data.

International Journal of Molecular Sciences 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, Formula: C5H6N2O2.

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

Colasurdo, Diego D. published the artcileTautomerism of uracil and related compounds and mass spectrometry study, SDS of cas: 608-34-4, the publication is European Journal of Mass Spectrometry (2018), 24(2), 214-224, database is CAplus and MEDLINE.

It has been demonstrated that uracil has a preponderant tautomeric form, but it is also known that different tautomers co-exist in this equilibrium In this work, mass spectrometry is used as a helpful tool to analyze the equilibrium, using derivative compounds to forbid the presence of some tautomers and ion trap mass spectrometry to follow relevant fragmentation pathways. Theor. calculations were performed to confirm tautomers abundance by energy minimization in gas phase. Anal. of mass spectra of uracil, three methyl-substituted uracils, 2-thiouracil and three benzouracils suggest that uracil exists mainly as three tautomers in gas phase and one major structure that corresponds to the classical structure of uracil (pyrimidine-2,4(1H,3H)-dione) bearing two carbonyls and two NH moieties, and two minor enolic forms (4-hydroxypyrimidin-2(1H)-one and 2-hydroxypyrimidin-4(1H)-one). Such tautomeric distribution is supported by theor. calculations, which show that they are the three most stable tautomers.

European Journal of 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, SDS of cas: 608-34-4.

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

Brunetti, Bruno published the artcileSublimation Enthalpies of Some Methyl Derivatives of Uracil from Vapor Pressure Measurements, Safety of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of Chemical and Engineering Data (2000), 45(2), 242-246, database is CAplus.

The standard sublimation enthalpies for uracil, 1-methyluracil, 3-methyluracil, and 1,3-dimethyluracil, Δ_subH°(298 K) = (128 ± 2), (124 ± 5), (121 ± 4), and (118 ± 4) kJ mol^-1, resp., were determined from their vapor pressures measured by the torsion method. The results of vapor pressure measurements were fit to the following linear equations: uracil, log(p/kPa) = (12.29 ± 0.15) – (6634 ± 100) K/T (from 384 K to 494 K); 1-methyluracil, log(p/kPa) = (13.75 ± 0.15) – (6357 ± 150) K/T (from 343 K to 428 K); 3-methyluracil, log(p/kPa) = (13.59 ± 0.10) – (6210 ± 100) K/T (from 344 K to 419 K); 1,3-dimethyluracil, log(p/kPa) = (15.10 ± 0.10) – (6049 ± 100) K/T (from 311 K to 364 K). The different sublimation behavior of some compounds can be due to the presence of hydrogen bonds in their solid state.

Journal of Chemical and Engineering Data 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, Safety of 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Szczepaniak, K. published the artcileMatrix isolation and DFT quantum mechanical studies of vibrational spectra of uracil and its methylated derivatives, Application In Synthesis of 608-34-4, the publication is Polish Journal of Chemistry (1998), 72(2), 402-420, database is CAplus.

The IR spectra of uracil and its derivatives in the carbonyl region are strikingly complex, and extremely sensitive to substitution, particularly at ring nitrogens. The IR spectra of uracil, 1,3-di-deuterouracil, 1-methyluracil, 3-methyluracil and 1,3-dimethyluracil were studied exptl. by low temperature (12 K) matrix isolation IR spectroscopic techniques, and theor. by DFT/B3LYP/6-31G(d,p) quantum mech. methods. Particular attention is focused on the carbonyl region and on the mech. coupling of the C2= and C4=O stretching vibrations with each other, with the N1H and N3H bending motions, and with other motions. This coupling plays a crucial role in determining the frequencies and intensities of the normal modes that determine the spectral patterns in the IR spectrum in the carbonyl region. The extreme sensitivity of the frequencies, intensities and spectral pattern in the carbonyl region to isotopic substitution and methylation (and to the intermol. interactions, particularly H bonding) is attributed, to a large extent, to changes in this coupling. The DFT calculations appear to give quite accurate values for the force constants and allow separation of simple mass effects and chem. substituent effects on the coupling. Fermi resonance in the carbonyl region is an important factor contributing to the observed complexity of this spectral region. Examination of this effect making use of the visualization of normal modes of vibration provides rules for when it may be expected to be important.

Polish Journal of 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 C13H18N2, Application In Synthesis of 608-34-4.

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