Category: pyrimidines

Wancewicz, Edward V. published the artcilePeptide Nucleic Acids conjugated to short basic peptides show improved pharmacokinetics and antisense activity in adipose tissue, Product Details of C26H26N4O7, the publication is Journal of Medicinal Chemistry (2010), 53(10), 3919-3926, database is CAplus and MEDLINE.

A peptide nucleic acid (PNA) targeting a splice junction of the murine PTEN primary transcript was covalently conjugated to various basic peptides. When systemically administered to healthy mice, the conjugates displayed sequence-specific alteration of PTEN mRNA splicing as well as inhibition of full length PTEN protein expression. Correlating activity with drug concentration in various tissues indicated strong tissue-dependence, with highest levels of activity observed in adipose tissue. While the presence of a peptide carrier was found to be crucial for efficient delivery to tissue, little difference was observed between the various peptides evaluated. A second PNA-conjugate targeting the murine insulin receptor primary transcript showed a similar activity profile, suggesting that short basic peptides can generally be used to effectively deliver peptide nucleic acids to adipose tissue.

Journal of Medicinal 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 C9H22OSi, Product Details of C26H26N4O7.

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

Wancewicz, Edward V. published the artcilePeptide Nucleic Acids conjugated to short basic peptides show improved pharmacokinetics and antisense activity in adipose tissue, SDS of cas: 186046-81-1, the publication is Journal of Medicinal Chemistry (2010), 53(10), 3919-3926, database is CAplus and MEDLINE.

A peptide nucleic acid (PNA) targeting a splice junction of the murine PTEN primary transcript was covalently conjugated to various basic peptides. When systemically administered to healthy mice, the conjugates displayed sequence-specific alteration of PTEN mRNA splicing as well as inhibition of full length PTEN protein expression. Correlating activity with drug concentration in various tissues indicated strong tissue-dependence, with highest levels of activity observed in adipose tissue. While the presence of a peptide carrier was found to be crucial for efficient delivery to tissue, little difference was observed between the various peptides evaluated. A second PNA-conjugate targeting the murine insulin receptor primary transcript showed a similar activity profile, suggesting that short basic peptides can generally be used to effectively deliver peptide nucleic acids to adipose tissue.

Journal of Medicinal 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 C6H16OSi, SDS of cas: 186046-81-1.

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

Wei, Xia published the artcileSelectable and releasable noncovalent functionalization of semiconducting SWCNTs by biethynyl-2,5-bis(dodecoxy)benzene unit-containing conjugated copolymers, Computed Properties of 56-05-3, the publication is Macromolecular Chemistry and Physics (2020), 221(13), 2000086, database is CAplus.

A rigid structural unit diethynyl-2,5-bis(dodecoxy)benzene (DDB) is proposed to functionalize single-walled carbon nanotubes (SWCNTs) with the assistance of pyrimidine ring. The effectiveness of conjugated polymer extraction of semiconducting SWCNTs is demonstrated by absorption and Raman spectroscopy. The protonated pyrimidine ring by the trifluoroacetic acid is used to reduce the interaction between polymer and SWCNTs that the bound wrapping polymer can be removed from the sorted SWCNTs, and mol. dynamics simulations of the binding ability of DDB and pyrimidine units to SWCNTs are conducted to further illustrate the strong binding ability of DDB units to SWCNTs. Therefore, this work provides an effective structural and theor. reference for polymer separation or modification of semiconducting SWCNTs.

Macromolecular Chemistry and Physics 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 C8H5F3O3, Computed Properties of 56-05-3.

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

Gaglione, Maria published the artcileSynthesis and biological properties of caffeic acid-PNA dimers containing guanine, Quality Control of 169396-92-3, the publication is Molecules (2013), 9147-9162, database is CAplus and MEDLINE.

Caffeic acid (CA; 3,4-dihydroxycinnamic acid) is endowed with high antioxidant activity. CA derivatives (such as amides) have gained a lot of attention due to their antioxidative, antitumor and antimicrobial properties as well as stable characteristics. Caffeoyl-peptide derivatives showed different antioxidant activity depending on the type and the sequence of amino acid used. For these reasons, the authors decided to combine CA with peptide nucleic acid (PNA) to test whether the new PNA-CA amide derivatives would result in an improvement or gain of CA biol. (i.e., antioxidant, cytotoxic, cytoprotective) properties. The authors performed the synthesis and characterization of seven dimer conjugates with various combinations of nucleic acid bases and focused NMR studies on the model compound ga-CA dimer. It was demonstrated that PNA dimers containing guanine conjugated to CA exhibited different biol. activities depending on composition and sequence of the nucleobases. One dimer (ag-CA) protected HepG2, SK-B-NE(2), and C6 cells from a cytotoxic dose of hydrogen peroxide (H₂O₂). The title compounds thus formed included a caffeic acid derivative (I). The synthesis of the target compound was achieved by an amidation of caffeic acid [(2E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid] with N-[2-(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)acetyl]-N-[2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]ethyl]glycine.

Molecules 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, Quality Control of 169396-92-3.

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

Shkurko, O. P. published the artcileNMR spectra of pyrimidines. Effect of substituents on the chemical shift of meta-protons in 2- and 4-substituted pyrimidines, Product Details of C6H9N3, the publication is Khimiya Geterotsiklicheskikh Soedinenii (1978), 673-7, database is CAplus.

NMR chem. shifts were recorded for H-4 in I (R = Me₂N, MeO, Me, Ph, H, halo, CO₂Me, MeSO₂, CN) and for H-2 and H-6 in II (same R), and correlation equations with F and R substituent constants were obtained. The inductive effect of R was weaker when R and the observed H were separated by a ring N.

Khimiya Geterotsiklicheskikh Soedinenii 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 C39H35N5O8, Product Details of C6H9N3.

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

Shkurko, O. P. published the artcileNMR spectra of pyrimidines. Effect of substituents on a chemical shift of amino group protons of p-substituted 2- and 5-aminopyrimidines and anilines, Product Details of C5H4N4, the publication is Khimiya Geterotsiklicheskikh Soedinenii (1979), 1683-6, database is CAplus.

NMR data for 4-substituted anilines, 5-substituted 2-aminopyrimidines, and 2-substituted 5-aminopyrimidines were subjected to correlation anal. The inductive effects were transmitted approx. equally through the benzene and pyrimidine rings. The conjugation effects were transmitted with equal efficiency through the benzene ring and from position 5 to position 2 of the pyrimidine ring; transmission from position 2 to position 5 of the pyrimidine ring was somewhat more efficient.

Khimiya Geterotsiklicheskikh Soedinenii 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 C40H35N7O8, Product Details of C5H4N4.

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

Huang, Pan published the artcileDiscovery of a Dual Tubulin Polymerization and Cell Division Cycle 20 Homologue Inhibitor via Structural Modification on Apcin, Recommanded Product: 2-Amino-4,6-dichloropyrimidine, the publication is Journal of Medicinal Chemistry (2020), 63(9), 4685-4700, database is CAplus and MEDLINE.

Apcin is one of the few compounds that have been previously reported as a Cdc20 specific inhibitor, although Cdc20 is a very promising drug target. We reported here the design, synthesis, and biol. evaluations of 2,2,2-trichloro-1-aryl carbamate derivatives as Cdc20 inhibitors. Among these derivatives, compound 9f(I) was much more efficient than the pos. compound apcin in inhibiting cancer cell growth, but it had approx. the same binding affinity with apcin in SPR assays. It is possible that another mechanism of action might exist. Further evidence demonstrated that compound 9f also inhibited tubulin polymerization, disorganized the microtubule network, and blocked the cell cycle at the M phase with changes in the expression of cyclins. Thus, it induced apoptosis through the activation of caspase-3 and PARP. In addition, compound 9f inhibited cell migration and invasion in a concentration-dependent manner. These results provide guidance for developing the current series as potential new 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, Recommanded Product: 2-Amino-4,6-dichloropyrimidine.

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

Farmer, Luc J. published the artcileDiscovery of VX-509 (Decernotinib): A Potent and Selective Janus Kinase 3 Inhibitor for the Treatment of Autoimmune Diseases, Application In Synthesis of 934178-97-9, the publication is Journal of Medicinal Chemistry (2015), 58(18), 7195-7216, database is CAplus and MEDLINE.

While several therapeutic options exist, the need for more effective, safe, and convenient treatment for a variety of autoimmune diseases persists. Targeting the Janus tyrosine kinases (JAKs), which play essential roles in cell signaling responses and can contribute to aberrant immune function associated with disease, has emerged as a novel and attractive approach for the development of new autoimmune disease therapies. We screened our compound library against JAK3, a key signaling kinase in immune cells, and identified multiple scaffolds showing good inhibitory activity for this kinase. A particular scaffold of interest, the 1H-pyrrolo[2,3-b]pyridine series (7-azaindoles), was selected for further optimization in part on the basis of binding affinity (K_i) as well as on the basis of cellular potency. Optimization of this chem. series led to the identification of VX-509 (decernotinib), a novel, potent, and selective JAK3 inhibitor, which demonstrates good efficacy in vivo in the rat host vs. graft model (HvG). On the basis of these findings, it appears that VX-509 offers potential for the treatment of a variety of autoimmune diseases.

Journal of Medicinal Chemistry published new progress about 934178-97-9. 934178-97-9 belongs to pyrimidines, auxiliary class Other Aromatic Heterocyclic,Boronic acid and ester,Sulfamide,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester,, name is 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, and the molecular formula is C19H22BN3O4S, Application In Synthesis of 934178-97-9.

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

Kurinovich, Mary Ann published the artcileThe acidity of uracil and uracil analogs in the gas phase: four surprisingly acidic sites and biological implications, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of the American Society for Mass Spectrometry (2002), 13(8), 985-995, database is CAplus and MEDLINE.

The gas phase acidities of a series of uracil derivatives (1-methyluracil, 3-methyluracil, 6-methyluracil, 5,6-dimethyluracil, and 1,3-dimethyluracil) have been bracketed to provide an understanding of the intrinsic reactivity of uracil. The experiments indicate that in the gas phase, uracil has four sites more acidic than water. Among the uracil analogs, the N1-H sites have ΔH_acid values of 331-333 kcal mol^-1; the acidity of the N3 sites fall between 347-352 kcal mol^-1. The vinylic C6 in 1-methyluracil and 3-methyluracil brackets to 363 kcal mol^-1, and 369 kcal mol^-1 in 1,3-dimethyluracil; the C5 of 1,3-dimethyluracil brackets to 384 kcal mol^-1. Calculations conducted at B3LYP/6-31+G are in agreement with the exptl. values. The bracketing of several of these sites involved utilization of an FTMS protocol to measure the less acidic site in a mol. that has more than one acidic site, establishing the generality of this method. In mols. with multiple acidic sites, only the two most acidic sites were bracketable, which is attributable to a kinetic effect. The measured acidities are in direct contrast to solution acidities, where the two most acidic sites of uracil (N1 and N3) are cannot be differentiated. The vinylic C6 site is also particularly acidic, compared to acrolein and pyridine. The biol. implications of these results particularly with respect to enzymes for which uracil is a substrate are discussed.

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

Kurinovich, Mary Ann published the artcileThe Acidity of Uracil from the Gas Phase to Solution: The Coalescence of the N1 and N3 Sites and Implications for Biological Glycosylation, Category: pyrimidines, the publication is Journal of the American Chemical Society (2000), 122(26), 6258-6262, database is CAplus.

The gas-phase acidities of the N1 and N3 sites of uracil have been bracketed to provide an understanding of the intrinsic reactivity of this nucleic base. The experiments indicate that in the gas phase, the N3 site is far less acidic (ΔH_acid = 347 ± 4 kcal mol^-1) than the N1 site (ΔH_acid = 333 ± 4 kcal mol^-1), in direct contrast to in solution, where the two sites are so close in acidity as to be unresolvable. This intrinsic difference and the coalescence in solution is interpreted through gas-phase and dielec.-medium calculations The results point to a possible chem. reason that N1 is the preferred glycosylation site in nature: nature may simply take advantage of the differential N1 and N3 acidities in a nonpolar environment to achieve selectivity.

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 C5H6N2O2, Category: pyrimidines.

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