Category: pyrimidines

Mueller, Andreas published the artcileProbing the Watson-Crick, Wobble, and Sugar-Edge Hydrogen Bond Sites of Uracil and Thymine, Computed Properties of 608-34-4, the publication is Journal of Physical Chemistry A (2005), 109(23), 5055-5063, database is CAplus and MEDLINE.

The nucleobases uracil (U) and thymine (T) offer three hydrogen-bonding sites for double H-bond formation via neighboring N-H and C:O groups, giving rise to the Watson-Crick, wobble and sugar-edge hydrogen bond isomers. The hydrogen bond properties of all three sites by forming hydrogen bonded dimers of U, 1-methyluracil (1MU), 3-methyluracil (3MU), and T with 2-pyridone (2PY) are probed. The mass- and isomer-specific S₁ ← S₀ vibronic spectra of 2PY·U, 2PY·3MU, 2PY·1MU, and 2PY·T were measured using UV laser resonant two-photon ionization (R2PI). The spectra of the Watson-Crick and wobble isomers of 2PY·1MU were separated using UV-UV spectral hole-burning. The different isomers are identified by combining three different diagnostic tools: (1) Selective methylation of the uracil N3-H group, which allows formation of the sugar-edge isomer only, and methylation of the N1-H group, which leads to formation of the Watson-Crick and wobble isomers. (2) The exptl. S₁ ← S₀ origins exhibit large spectral blue shifts relative to the 2PY monomer. Ab initio CIS calculations of the spectral shifts of the different hydrogen-bonded dimers show a linear correlation with experiment This correlation allows the identification of the R2PI spectra of the weakly populated Watson-Crick and wobble isomers of both 2PY·U and 2PY·T. (3) PW91 d. functional calculation of the ground-state binding and dissociation energies D_e and D₀ are in agreement with the assignment of the dominant hydrogen bond isomers of 2PY·U, 2PY·3MU and 2PY·T as the sugar-edge form. For 2PY·U, 2PY·T and 2PY·1MU the measured wobble:Watson-Crick:sugar-edge isomer ratios are in good agreement with the calculated ratios, based on the ab initio dissociation energies and gas-phase statistical mechanics. The Watson-Crick and wobble isomers are thereby determined to be several kcal/mol less strongly bound than the sugar-edge isomers. The 36 observed intermol. frequencies of the nine different H-bonded isomers give detailed insight into the intermol. force field.

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, Computed Properties of 608-34-4.

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

Gebauer, Sabine published the artcileHigh performance liquid chromatography on calixarene-bonded silica gels. II. Separations of regio- and stereoisomers on p-tert-butylcalix[n]arene phases, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of Chromatographic Science (1998), 36(8), 383-387, database is CAplus.

The chromatog. behavior of new calix[n]arene-bonded (n = 4, 6, 8) silica gels are described. Cavities of different size and shape are formed depending on the number of aromatic moieties. The differences in ring size were used to study chromatog. selectivities towards analytes of various substance classes, including disubstituted aromatics, uracil derivatives, and estradiol epimers. The authors’ results indicate that these calixarene-bonded phases show a high resolution power for regio- and stereoisomers.

Journal of Chromatographic Science 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

Chantell, Christina A. published the artcileLow-cost, automated synthesis of a PNA-peptide conjugate on a peptide synthesizer, Name: 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, the publication is American Biotechnology Laboratory (2009), 27(8), 8-10, database is CAplus.

Two peptide nucleic acid (PNA) sequences, one containing a lysine residue at the C-terminus and the other containing a peptide analog of LH-releasing hormone, were synthesized in an automated peptide synthesizer. The PNA sequence was constructed from protected monomers, Fmoc-A(Bhoc)aeg-OH, Fmoc-C(Bhoc)aeg-OH, Fmoc-G(Bhoc)aeg-OH and Fmoc-T-aeg-OH, which were coupled to Fmoc-Lys(Boc)-Wang resin using HATU as a coupling reagent. This work demonstrated the successful automated synthesis of a PNA sequence and a PNA-peptide conjugate on “Prelude” automated peptide synthesizer which enabled minimizing overall consumption and costs.

American Biotechnology Laboratory published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Name: 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid.

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

Burrow, P. D. published the artcileVibrational Feshbach resonances in uracil and thymine, Formula: C5H6N2O2, the publication is Journal of Chemical Physics (2006), 124(12), 124310/1-124310/7, database is CAplus and MEDLINE.

Sharp peaks in the dissociative electron attachment (DEA) cross sections of uracil and thymine at energies below 3 eV are assigned to vibrational Feshbach resonances (VFRs) arising from coupling between the dipole bound state and the temporary anion state associated with occupation of the lowest σ^* orbital. Three distinct vibrational modes are identified, and their presence as VFRs is consistent with the amplitudes and bonding characteristics of the σ^* orbital wave function. A deconvolution method is also employed to yield higher effective energy resolution in the DEA spectra. The site dependence of DEA cross sections is evaluated using Me substituted uracil and thymine to block H atom loss selectively. Implications for the broader issue of DNA damage are briefly discussed.

Journal of 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, Formula: C5H6N2O2.

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

Wang, Zhisong published the artcileStructure-Based Design of Highly Potent Toll-like Receptor 7/8 Dual Agonists for Cancer Immunotherapy, Name: 2-Amino-6-chloropyrido[3,2-d]pyrimidin-4(1H)-one, the publication is Journal of Medicinal Chemistry (2021), 64(11), 7507-7532, database is CAplus and MEDLINE.

Design and synthesis of a series of pyrido[3,2-d]pyrimidine-based toll-like receptor 7/8 dual agonists, e.g., I that exhibited potent and near-equivalent agonistic activities toward TLR7 and TLR8. In vitro, compounds significantly induced the secretion of IFN-α, IFN-γ, TNF-α, IL-1β, IL-12p40, and IP-10 in human peripheral blood mononuclear cell assays. In vivo, compounds significantly suppressed tumor growth in CT26 tumor-bearing mice by remodeling the tumor microenvironment. Addnl., compounds markedly improved the antitumor activity of PD-1/PD-L1 blockade. These results demonstrated that TLR7/8 agonists held great potential as single agents or in combination with PD-1/PD-L1 blockade for cancer immunotherapy.

Journal of Medicinal Chemistry published new progress about 897359-74-9. 897359-74-9 belongs to pyrimidines, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine,Amide, name is 2-Amino-6-chloropyrido[3,2-d]pyrimidin-4(1H)-one, and the molecular formula is C14H20BNO3, Name: 2-Amino-6-chloropyrido[3,2-d]pyrimidin-4(1H)-one.

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

Li, Xue-Dong published the artcileA NaI/H₂O₂-Mediated Sulfenylation and Selenylation of Unprotected Uracil and Its Derivatives, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Organic Letters (2019), 21(17), 6643-6647, database is CAplus and MEDLINE.

An efficient iodide-catalyzed/hydrogen peroxide mediated sulfenylation and selenylation of unprotected uracil and its derivatives with simple thiols and diselenides was established. This coupling tolerates a broad variety of functional groups to provide diverse 5-sulfur/selenium-substituted uracil derivatives in good to excellent yields (up to 93%).

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

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

Husken, Nina published the artcile“Four-Potential” Ferrocene Labeling of PNA Oligomers via Click Chemistry, HPLC of Formula: 186046-81-1, the publication is Bioconjugate Chemistry (2009), 20(8), 1578-1586, database is CAplus and MEDLINE.

The scope of the Cu(I)-catalyzed [2 + 3] azide/alkyne cycloaddition (CuAAC, click chem.) as a key reaction for the conjugation of ferrocene derivatives to N-terminal functionalized PNA oligomers is explored herein (PNA: peptide nucleic acid). The facile solid-phase synthesis of N-terminal azide or alkyne-functionalized PNA oligomer precursors and their cycloaddition with azidoferrocene, ethynylferrocene, and N-(3-ethylpent-1-yn-3-yl)ferrocene-carboxamide (DEPA-ferrocene) on the solid phase are presented. While the click reaction with azidomethylferrocene worked equally well, the ferrocenylmethyl group is lost from the conjugate upon acid cleavage. However, the desired product was obtained via a post-SPPS conversion of the alkyne-PNA oligomer with azidomethylferrocene in solution The synthesis of all ferrocene-PNA conjugates (trimer t₃-PNA, 3, 4, 5, 6; 12mer PNA, 10 – t c t a c a a g a c t c, 11 – t c t a c c g t a c t c) succeeded with excellent yields and purities, as determined by mass spectrometry and HPLC. Electrochem. studies of the trimer Fc-PNA conjugates 3, 4, 5, and 6 with four different ferrocene moieties revealed quasi-reversible redox processes of the ferrocenyl redox couple Fc^0/+ and electrochem. half-wave potentials in a range of E_1/2 = -20 mV to +270 mV vs FcH^0/+ (Fc: ferrocenyl, C₁₀H₉Fe). The observed potential differences ΔE_1/2^min are always greater than 60 mV for any given pair of Fc-PNA conjugates, thus allowing a reliable differentiation with sensitive electrochem. methods like e.g. square wave voltammetry (SWV). This is the electrochem. equivalent of “four-color” detection and is hence denoted “four-potential” labeling. Preparation and electrochem. investigation of the set of four structurally different and electrochem. distinguishable ferrocenyl groups conjugated to PNA oligomers, as exemplified by the conjugates 3, 4, 5, and 6, demonstrates the scope of the azide/alkyne cycloaddition for the labeling of PNA with electrochem. active ferrocenyl groups. Furthermore, it provides a PNA-based system for the electrochem. detection of single-nucleotide polymorphism (SNP) in DNA/RNA.

Bioconjugate Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, HPLC of Formula: 186046-81-1.

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

Sosniak, Anna M. published the artcileThermal melting studies of alkyne- and ferrocene-containing PNA bioconjugates, Recommanded Product: 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, the publication is Organic & Biomolecular Chemistry (2009), 7(23), 4992-5000, database is CAplus and MEDLINE.

The preparation of new metal-containing peptide nucleic acids (PNAs) is currently a field of research intensively studied for various purposes, such as DNA biosensors. The role played by the metal center, notably on the stability of the PNA·DNA hybrid, is obviously crucial, but has not yet been fully investigated. In this work, UV-Vis spectroscopic measurements of solutions of DNA·PNA hybrids, whose 11/12-mer PNA oligomers contained either alkynyl PNA monomer I or ferrocene-containing PNA monomer II, were carried out to determine the effect of these monomers on the thermal stability of the hybrids (PNA = H-Gly-X-gggtc-Y-agctt-X-Lys-NH₂; X, Y = I, II, blank position). Supplementary CD spectroscopic measurements were performed to gain insight into the structures of the PNA·DNA duplexes formed. The effect of both modified monomers was found to depend on their actual positions within the PNA sequences. Insertions at the N- or C-termini of a PNA oligomer did not change the melting temperatures (T_m values of about 72°) of the DNA·PNA hybrids significantly. Insertion of monomers I or II in the middle of a PNA sequence induced a substantial decrease in the T_m of the hybrids (by about 23°) when bound to the same DNA oligomer. Interestingly, it was found that the type of modification, namely alkyne or ferrocene, did not significantly influence the T_m values in these cases. However, the thermal stability of hybrids with the DNA oligomers containing one to four addnl. thymines and the PNA oligomers containing the ferrocene moiety in its middle, varied significantly with the number of thymines added compared to its alkyne analogs (ΔT_m up to -13°). The presence of the ferrocene moiety induced a significant decrease in thermal stability of the hybrids, probably due to its bulkiness. In order to assess the effect of PNA backbone rigidity on the stability of DNA·PNA hybrids, PNA oligomers with an internal amino acid, propargylglycine (Pgl) or the dipeptide glycine-propargylglycine (Gly-Pgl), were synthesized. It was assumed that the orientation of the alkyne moiety in the Pgl-containing PNA sequence is not identical to an alkyne-containing PNA sequence, as a significantly higher T_m value (ΔT_m = +10°) was measured. It is anticipated that the alkyne moiety in Pgl is not facing the DNA base and therefore does not disturb as much the neighboring nucleobases and base-stacking of the complementary DNA, in contrast to the alkyne moiety of I. Interestingly, no significant differences in the thermal stability of the hybrids was observed between Pgl-containing and dipeptide-containing PNA oligomers, although the former contracts the PNA backbone by three atoms.

Organic & Biomolecular Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C9H22OSi, Recommanded Product: 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid.

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

Johansen, Martin B. published the artcileAccess to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO, SDS of cas: 56-05-3, the publication is Organic Letters (2020), 22(11), 4068-4072, database is CAplus and MEDLINE.

A sequential one-pot preparation of aromatic trifluoromethyl ketones RC(O)CF₃ (R = 3,5-dimethoxyphenyl, quinolin-3-yl, 4-adamantylphenyl, etc.) starting from readily accessible aryl bromides/fluorosulfates RX (X = Br, OS(O)₂F), the latter easily prepared from the corresponding phenols ROH were reported. The methodol. utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing ¹³C-isotopically labeled TFMK by switching to the use of ¹³COgen.

Organic Letters published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, SDS of cas: 56-05-3.

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

Kheifets, G. M. published the artcileEffect of the structure of 1- and 3-methylpyrimidin-4-ones on the rate of nucleophilic substitution of the 2-methylsulfanyl group, Synthetic Route of 608-34-4, the publication is Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) (2004), 40(1), 104-113, database is CAplus.

Rate constants for substitution of the 2-methylsulfanyl group in 1- and 3-methyl-2-methylsulfanylpyrimidin-4-ones and their 5-fluoro analogs were measured in the reaction with butylamine, alk. hydrolysis, and methanolysis. The rate of substitution in 1-Me isomers having a zwitterionic structure is greater by a factor of ∼2 than the rate of substitution in 3-Me isomers with conjugated double bonds in the ring. The presence of a fluorine atom in position 5 accelerates nucleophilic substitution in 1-Me isomers, while 5-fluoro-3-methyl-2-methylsulfanylpyrimidin-4-ones react at a lower rate than their 5-unsubstituted analogs. According to the NMR data, the reactions involve formation of a tetrahedral intermediate. Anchimeric effect of the Me group on N¹ hampers attack by basic reagent on the C⁶ atom.

Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) 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, Synthetic Route of 608-34-4.

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