Pyrimidines

Shkurko, O. P. published the artcileEquilibrium NH-acidity of substituted aminopyrimidines, SDS of cas: 56621-93-3, the publication is Zhurnal Organicheskoi Khimii (1981), 17(2), 312-17, database is CAplus.

The transmetalation method was used to determine the NH acidity (pK) of thirty-nine 2-, 4-, and 5-aminopyrimidines; the pK values ranged from 17.7 for 5-nitro-2-pyrimidinamine to 30.2 for 2-(dimethylamino)-5-pyrimidinamine. Comparison with the pK of aniline showed that the ring N atoms had an acidifying effect in the order 4-aza ≫ 2-aza > 3-aza. LFER of the pK vs. NMR chem. shifts, and inductive or resonance substituent constants were described.

Zhurnal Organicheskoi Khimii published new progress about 56621-93-3. 56621-93-3 belongs to pyrimidines, auxiliary class Pyrimidine,Nitrile,Amine, name is 5-Aminopyrimidine-2-carbonitrile, and the molecular formula is C17H37NO3, SDS of cas: 56621-93-3.

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

Walunj, Manisha B. published the artcilePost-transcriptional labeling by using Suzuki-Miyaura cross-coupling generates functional RNA probes, Safety of 2-(Dimethylamino)pyrimidine-4,6-diol, the publication is Nucleic Acids Research (2018), 46(11), e65/1-e65/10, database is CAplus and MEDLINE.

Pd-catalyzed C-C bond formation, an important vertebra in the spine of synthetic chem., is emerging as a valuable chemoselective transformation for post-synthetic functionalization of biomacromols. While methods are available for labeling protein and DNA, development of an analogous procedure to label RNA by cross-coupling reactions remains a major challenge. Herein, we describe a new Pd-mediated RNA oligonucleotide (ON) labeling method that involves post-transcriptional functionalization of iodouridine-labeled RNA transcripts by using Suzuki-Miyaura cross-coupling reaction. 5-Iodouridine triphosphate (IUTP) is efficiently incorporated into RNA ONs at one or more sites by T7 RNA polymerase. Further, using a catalytic system made of Pd(OAc)2 and 2-aminopyrimidine- 4,6-diol (ADHP) or dimethylamino-substituted ADHP (DMADHP), we established a modular method to functionalize iodouridine-labeled RNA ONs in the presence of various boronic acid and ester substrates under very mild conditions (37°C and pH 8.5). This method is highly chemoselective, and offers direct access to RNA ONs labeled with commonly used fluorescent and affinity tags and new fluorogenic environment-sensitive nucleoside probes in a ligand-controlled stereoselective fashion. Taken together, this simple approach of generating functional RNA ON probes by Suzuki-Miyaura coupling will be a very important addition to the resources and tools available for analyzing RNA motifs.

Nucleic Acids Research published new progress about 5738-14-7. 5738-14-7 belongs to pyrimidines, auxiliary class Pyrimidine,Amine,Alcohol,Pyrimidine, name is 2-(Dimethylamino)pyrimidine-4,6-diol, and the molecular formula is C4H5NS2, Safety of 2-(Dimethylamino)pyrimidine-4,6-diol.

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

Iltzsch, Max H. published the artcileStructure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Biochemical Pharmacology (1994), 48(4), 781-91, database is CAplus and MEDLINE.

One hundred compounds were evaluated as ligands of Toxoplasma gondii, uracil phosphoribosyltransferase (UPRTase, EC 2.4.2.9) by examining their ability to inhibit this enzyme in vitro. Inhibition was quantified by determining apparent K_i values fo those compounds that inhibited T. gondii UPRTase by greater than 10% at a concentration of 2 mM. Five compounds (4-thiopyridine, 2-thiopyrimidine, trihiocyanuric acid, 1-deazauracil and 2,4-dithiouracil) bound to the enzyme better than two known substrates for T. gondii UPRTase, 5-fluorouracil and emimycin, which have antitoxoplasmal activity (Pfefferkorn ER, Exp Parasitol 44: 26-35, 1978; Pfefferkorn et al., Exp Parasitol 69: 129-139, 1989). In addition, several selected compounds were evaluated as substrates for T. gondii UPRTase, and it was found that 2,4-dithiouracil is also a substrate for this enzyme. On the basis of these data, a structure-activity relationship for the binding of ligands to T. gondii UPRTase was determined using uracil as a reference compound

Biochemical Pharmacology 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

Liu, Mingyu published the artcileAtom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes, Quality Control of 174456-28-1, the publication is Journal of the American Chemical Society (2021), 143(10), 3881-3888, database is CAplus and MEDLINE.

Herein, a selective and catalytic method for synthesizing 1,3-enynes (E/Z)-RCCC(R¹)=CHR² (R = tris(propan-2-yl)silyl, 4-(acetyloxy)butyl, cyclohexylmethyl, 5-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)pentyl, etc.; R¹ = Et, Ph, pyridin-3-yl, pyrimidin-5-yl, etc.; R² = hydroxymethyl, (phenylformamido)methyl, [(1H-indol-5-yl)carbamoyl]methyl, etc.) without prefunctionalized building blocks was described. This method is facilitated by a tailored P,N-ligand that enables regioselective dimerization and suppresses secondary E/Z-isomerization of the product. The transformation enables several classes of unactivated internal acceptor alkynes R¹CCR² to be coupled with terminal donor alkynes RCCH to deliver 1,3-enynes in a highly regio- and stereoselective manner. The scope of compatible acceptor alkynes includes propargyl alcs., (homo)propargyl amine derivatives, and (homo)propargyl carboxamides. The reaction is scalable and can operate effectively with as low as 0.5 mol% catalyst loading. The products are versatile intermediates that can participate in various downstream transformations. The preliminary mechanistic experiments that are consistent with a redox-neutral Pd(II) catalytic cycle were also presented.

Journal of the American Chemical Society published new progress about 174456-28-1. 174456-28-1 belongs to pyrimidines, auxiliary class Pyrimidine,Alkynyl,Alcohol, name is 3-(Pyrimidin-5-yl)prop-2-yn-1-ol, and the molecular formula is C7H6N2O, Quality Control of 174456-28-1.

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

Kang, Yanlong published the artcileHeat Shock Protein 70 Inhibitors. 1. 2,5′-Thiodipyrimidine and 5-(Phenylthio)pyrimidine Acrylamides as Irreversible Binders to an Allosteric Site on Heat Shock Protein 70, Related Products of pyrimidines, the publication is Journal of Medicinal Chemistry (2014), 57(4), 1188-1207, database is CAplus and MEDLINE.

Heat shock protein 70 (Hsp70) is an important emerging cancer target whose inhibition may affect multiple cancer-associated signaling pathways and, moreover, result in significant cancer cell apoptosis. Despite considerable interest from both academia and pharmaceutical companies in the discovery and development of druglike Hsp70 inhibitors, little success has been reported so far. Here we describe structure-activity relationship studies in the first rationally designed Hsp70 inhibitor class that binds to a novel allosteric pocket located in the N-terminal domain of the protein. These 2,5′-thiodipyrimidine and 5-(phenylthio)pyrimidine acrylamides take advantage of an active cysteine embedded in the allosteric pocket to act as covalent protein modifiers upon binding. The study identifies derivatives 17a and 20a, which selectively bind to Hsp70 in cancer cells. Addition of high nanomolar to low micromolar concentrations of these inhibitors to cancer cells leads to a reduction in the steady-state levels of Hsp70-sheltered oncoproteins, an effect associated with inhibition of cancer cell growth and apoptosis. In summary, the described scaffolds represent a viable starting point for the development of druglike Hsp70 inhibitors as novel anticancer therapeutics.

Journal of Medicinal Chemistry 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, Related Products of pyrimidines.

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

Palafox, M. Alcolea published the artcileQuantum Chemical Scaling and its Importance: The Infrared and Raman Spectra of 5-Bromouracil, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Spectroscopy Letters (2010), 43(1), 51-59, database is CAplus.

This work describes the interest and necessity of scaling to correct the deficiencies in the calculation of the harmonic vibrational wave numbers The use of adequate quantum-chem. methods and scaling procedures reduces the risk in the assignment and can also accurately determine the contribution of the different modes in an observed band. As an example, the IR and laser-Raman spectra of the 5-bromouracil biomol. are shown.

Spectroscopy 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, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Yamagami, Chisako published the artcileHydrophobicity parameter of diazines. 1. Analysis and prediction of partition coefficients of monosubstituted diazines, HPLC of Formula: 31401-45-3, the publication is Quantitative Structure-Activity Relationships (1990), 9(4), 313-20, database is CAplus.

The octanol/water partition coefficient (P) of a number of monosubstituted diazines was measured. The composition of the π value of substituents, the increment in the log P value accompanying the introduction of substituents, was examined in terms of physicochem. substituent parameters and correlation anal. The diazine-π value of substituents was generally higher than the pyridine-π value of corresponding substituents, indicating that the intramol. electronic interactions between the ring-N atoms and substituent are more pronounced than those in substituted pyridines in governing the log P value of the mol. Except for 2-substituted pyrimidines, the π value of substituents in each series of monosubstituted diazines was in general nicely correlated with the π value of the corresponding substituents in substituted pyridines along with electronic parameter terms representing bidirectional electronic effects on the relative solvation of the ring-N atom(s) and the hydrogen-bondable substituents with partitioning solvents according to the procedure proposed previously for the anal. of the π value in disubstituted benzenes and monosubstituted pyridines. Keeping in mind that 2-pyrimidines substituted by hydrogen-bondable groups sometimes behave as outliers, the correlations were believed to be usable for prediction of log P values of monosubstituted diazines.

Quantitative Structure-Activity Relationships 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 C5H6BNO2, HPLC of Formula: 31401-45-3.

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

Araki, Koji published the artcileDesign of a fluorescent host for monitoring multiple hydrogen-bonding interaction directly by intramolecular charge-transfer emission, Formula: C5H6N2O2, the publication is Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1998), 1391-1396, database is CAplus.

The hosts 2-dodecanamido-4-methyl-N-[4-(dimethylamino)phenyl]quinoline-7-carboxamide 1 and 2-dodecanamido-4-methyl-N-(4-methoxyphenyl)quinoline-7-carboxamide 2 bearing an aromatic amide unit exhibit an anomalous fluorescence with a large Stokes shift at around 500-600 nm (LW emission) due to an intramol. charge-transfer (ICT) process. The guests 3-ethyl-3-methylglutarimide (bemegride) 4 and 1-methyluracil 5 are associated with the hosts by forming three hydrogen bonds, and the LW emission of the hosts largely increases. On the other hand, the guest 3-methyluracil 6 does not affect the emission of the hosts at all, though formation of two hydrogen bonds with the hosts is confirmed by ¹H NMR measurement. It is concluded that the hosts 1 and 2 can selectively detect the guests 4 and 5 that form hydrogen bonds both at the quinoline ring nitrogen and the amide proton (H_α) of the hosts simultaneously to affect rotation of the amide bond.

Journal of the Chemical Society, Perkin Transactions 2: Physical 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, Formula: C5H6N2O2.

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

Ostakhov, S. S. published the artcileSpectral-luminescence and quantum-chemical study of the anionic forms of 5-fluorouracil, Product Details of C5H6N2O2, the publication is High Energy Chemistry (2017), 51(2), 108-112, database is CAplus.

A spectral-luminescence study of neutral (pH 7) and alk. (pH 11 and 14) aqueous solutions of the anticancer drugs 5-fluorouracil (FU) and tegafur has been performed. The fluorescence spectra of the N3- and N1-centered anions of 5-fluorouracil, its dianion, and the tegafur monoanion with emission maxima at wavelengths (λ_em) of 358, 372, 366, and 358 nm and photoluminescence quantum yields (φ) of 11.2 x 10^-4, 35.1 x 10^-4, 26.5 x 10^-4, and 8.6 x 10^-4, resp., have been recorded for the first time. The fluorescence characteristics of the FU anionic forms have been related to the magnetic shielding constant as one of the criteria of aromaticity.

High Energy 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

Muellar, Stefan published the artcile8-Vinylguanine Nucleo Amino Acid: A Fluorescent PNA Building Block, Recommanded Product: 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, the publication is Organic Letters (2012), 14(6), 1382-1385, database is CAplus and MEDLINE.

Attachment of a vinyl group at guanine position 8 provides fluorescent properties of the nucleobase. Therefore, 8-vinylguanine was introduced as a 2-aminoethylglycine peptide nucleic acid (PNA) building block. Incorporation of the guanine analog in short PNA sequences by Fmoc solid phase peptide synthesis allowed the differentiation between hybridization states of specific double strands with DNA, RNA, and PNA as well as quadruplex forming RNA/PNA oligomers based on fluorescence intensity.

Organic Letters 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, Recommanded Product: 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.

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