Day: November 21, 2022

El-Ghomari, K. published the artcileMetabolic N-oxygenation of 2,4-diamino-6-substituted pyrimidines, Synthetic Route of 74638-76-9, the publication is European Journal of Drug Metabolism and Pharmacokinetics (1987), 12(4), 253-8, database is CAplus and MEDLINE.

Biol. oxidation of 2,4-diamino-6-substituted pyrimidines was studied using hepatic microsomes from various mammalian species. The 3-N-oxides were formed with 6-pipeidino-, 6-diethylamino-, 6-methyl-, and 6-chloro-substituted 2,4-diaminopyrimidines: no evidence of 1-N-oxide formation was obtained. With the 6-hydroxy-, 6-amino-, and unsubstituted 2,4-diaminopyrimidines and melamine, no N-oxidative metabolite was detected. The differences in N-oxide formation is discussed in terms of the effect of substituents on tautomerism and electron distribution. The N-oxygenation was mediated via a cytochrome P 450-dependent system.

European Journal of Drug Metabolism and Pharmacokinetics published new progress about 74638-76-9. 74638-76-9 belongs to pyrimidines, auxiliary class Pyrimidine, name is 2,4-Diaminopyrimidine-3-oxide, and the molecular formula is C4H6N4O, Synthetic Route of 74638-76-9.

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

Panciera, Michele published the artcileInduced α,γ-cyclic peptide rotodimer recognition by nucleobase scaffolds, Recommanded Product: 2-(4-((tert-Butoxycarbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid, the publication is Peptide Science (Hoboken, NJ, United States) (2020), 112(1), e24132, database is CAplus.

The β-sheet-type structures derived from the stacking of α,γ-cyclic peptides to form peptides nanotubes can provide different topoisomers, nonequivalent cyclic peptide stacks generated by the relative rotation through the channel axis of one cyclic peptide with respect to the next component. This rotation generates a series of cyclic peptide dimers paired by the same type of hydrogen bond pattern but differentiated by the cross-strand side chain-side chain pairwise. The control of this peptide-peptide relative orientation in stacked supramol. aggregates is required for practical applications in material sciences, sensing, or biol. We propose the use of small oligonucleotides to control the prevalence of a particular dimer through the formation of specific hydrogen bonds between cyclic peptides bearing a nucleobase attached to a serine side chain with a complementary oligonucleotide (peptide nucleic acid).

Peptide Science (Hoboken, NJ, United States) published new progress about 172405-16-2. 172405-16-2 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide, name is 2-(4-((tert-Butoxycarbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid, and the molecular formula is C11H15N3O5, Recommanded Product: 2-(4-((tert-Butoxycarbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid.

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

Cruege, Francis published the artcileBasic properties of dimethylamino derivatives of pyridine and pyrimidine, Recommanded Product: N,N-Dimethylpyrimidin-4-amine, the publication is Bulletin de la Societe Chimique de France (1970), 3889-94, database is CAplus.

A correlation exists between the free enthalpy of complexation (with PhOH) and the intrinsic pKa of (dimethylamino)pyridines and -pyrimidines. 2-Dimethylamino isomers are the most basic compounds, and the steric hindrance effect of the 2-dimethylamino group is discussed.

Bulletin de la Societe Chimique de France published new progress about 31401-45-3. 31401-45-3 belongs to pyrimidines, auxiliary class Pyrimidine,Amine, name is N,N-Dimethylpyrimidin-4-amine, and the molecular formula is C6H9N3, Recommanded Product: N,N-Dimethylpyrimidin-4-amine.

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

Agramunt, Jordi published the artcileInverse Electron-Demand Diels-Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles, 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 Journal of Organic Chemistry (2020), 85(10), 6593-6604, database is CAplus and MEDLINE.

Oligonucleotides, peptides, and peptide nucleic acids incorporating 7-oxanorbornene as a dienophile were reacted with tetrazines linked to either a peptide, D-biotin, BODIPY, or N-acetyl-D-galactosamine. The inverse electron-demand Diels-Alder (IEDDA) cycloaddition, which was performed overnight at 37°C, in all cases furnished the target conjugate in good yields. IEDDA reactions with 7-oxanorbornenes produce a lower number of stereoisomers than that of IEDDA cycloadditions with other dienophiles.

Journal of Organic 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, 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

Agramunt, Jordi published the artcileInverse Electron-Demand Diels-Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles, Formula: C26H26N4O7, the publication is Journal of Organic Chemistry (2020), 85(10), 6593-6604, database is CAplus and MEDLINE.

Oligonucleotides, peptides, and peptide nucleic acids incorporating 7-oxanorbornene as a dienophile were reacted with tetrazines linked to either a peptide, D-biotin, BODIPY, or N-acetyl-D-galactosamine. The inverse electron-demand Diels-Alder (IEDDA) cycloaddition, which was performed overnight at 37°C, in all cases furnished the target conjugate in good yields. IEDDA reactions with 7-oxanorbornenes produce a lower number of stereoisomers than that of IEDDA cycloadditions with other dienophiles.

Journal of Organic Chemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Formula: C26H26N4O7.

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

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

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

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

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