Month: November 2022

Zhachkina, Anna published the artcileUracil and Thymine Reactivity in the Gas Phase: The S_N2 Reaction and Implications for Electron Delocalization in Leaving Groups, SDS of cas: 608-34-4, the publication is Journal of the American Chemical Society (2009), 131(51), 18376-18385, database is CAplus and MEDLINE.

The gas-phase substitution reactions of Me chloride and 1,3-dimethyluracil (at the N1-CH₃) are examined computationally and exptl. It is found that, although hydrochloric acid and 3-methyluracil are similar in acidity, the leaving group abilities of chloride and N1-deprotonated 3-methyluracil are not: chloride is a slightly better leaving group. The reason for this difference is most likely related to the electron delocalization in the N1-deprotonated 3-methyluracil anion, which we explore further herein. The leaving group ability of the N1-deprotonated 3-methyluracil anion relative to the N1-deprotonated 3-methylthymine anion is also examined in the context of an enzymic reaction that cleaves uracil but not thymine from DNA.

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 C5H5ClO2, SDS of cas: 608-34-4.

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

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

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

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

Mikhaleva, M. A. published the artcileSynthesis of Schiff bases of 2-substituted 5-aminopyrimidines and their mesomorphic properties, Computed Properties of 56621-93-3, the publication is Khimiya Geterotsiklicheskikh Soedinenii (1982), 1545-52, database is CAplus.

Schiff bases I (R = MeO, BuO, Me, Cl, CN, p-MeOC₆H₄, p-BuOC₆H₄, p-C₆H₁₃OC₆H₄, Ph, p-BrC₆H₄; R¹ = alkoxy, NO₂) were prepared in 32-100% yields by condensation of 4-R¹C₆H₄CHO with the corresponding aminopyrimidine and the liquid crystal properties (anisotropic dielec. permeability) of I (R, R¹ = MeO, C₆H₁₃O; BuO, C₈H₁₇O; Cl, C₉H₁₉O; CN, BuO; p-C₆H₁₃OC₆H₄, C₆H₁₃O) were determined

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 C5H4N4, Computed Properties of 56621-93-3.

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

Browne, Elisse C. published the artcileSynthesis and effects of conjugated tocopherol analogues on peptide nucleic acid hybridisation, Safety of 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 (2013), 11(39), 6744-6750, database is CAplus and MEDLINE.

To the N-terminus of a nonamer peptide nucleic acid sequence, H-GCACGACTT-NH₂, was attached a number of lipophilic conjugate mols. including three synthetic tocopherol (vitamin E) analogs. Studies were then undertaken with complementary PNA and DNA sequences to explore the effects of the conjugates using the techniques of UV monitored melting curves and isothermal calorimetry. Duplex formation was observed when the benzopyran group of vitamin E was conjugated. However, in the presence of the phytyl chain of vitamin E, binding was found to be temperature dependent.

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 C39H35N5O8, Safety of 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

Browne, Elisse C. published the artcilePeptide Nucleic Acid Monomers: A Convenient and Efficient Synthetic Approach to Fmoc/Boc Monomers, COA of Formula: C26H26N4O7, the publication is Australian Journal of Chemistry (2012), 65(5), 539-544, database is CAplus.

A convenient and cost-effective method for the synthesis of Fmoc/Boc-protected peptide nucleic acid monomers is described. The Fmoc/Boc strategy was developed in order to eliminate the solubility issues during peptide nucleic acid solid-phase synthesis, in particular that of the cytosine monomer, that occurred when using the commercialized Bhoc chem. approach.

Australian Journal of 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, COA of Formula: C26H26N4O7.

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

Browne, Elisse C. published the artcileSynthesis and effects of conjugated tocopherol analogues on peptide nucleic acid hybridisation, 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 & Biomolecular Chemistry (2013), 11(39), 6744-6750, database is CAplus and MEDLINE.

To the N-terminus of a nonamer peptide nucleic acid sequence, H-GCACGACTT-NH₂, was attached a number of lipophilic conjugate mols. including three synthetic tocopherol (vitamin E) analogs. Studies were then undertaken with complementary PNA and DNA sequences to explore the effects of the conjugates using the techniques of UV monitored melting curves and isothermal calorimetry. Duplex formation was observed when the benzopyran group of vitamin E was conjugated. However, in the presence of the phytyl chain of vitamin E, binding was found to be temperature dependent.

Organic & Biomolecular 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, 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

Yi, Wonhui published the artcileSynthesis and inhibitory activity on NF-κB activation of chroman-2-carboxylic acid N-heteroarylamide derivatives, HPLC of Formula: 56-05-3, the publication is Yakhak Hoechi (2012), 56(3), 186-190, database is CAplus.

Nuclear factor-κB (NF-κB) has been considered as one of the major targets for therapeutic agents of diverse human diseases. In the previous studies, 6-hydroxy-7-methoxychroman-2-carboxylic acid N-phenylamide (KL-1156) and chroman-2-carboxylic acid N-(4-chlorophenyl)amide were identified as good inhibitors of NF-κB activation. In this continuous study, we describe the synthesis and NF-κB inhibitory activities of chroman derivatives containing N-heteroaryl groups for exploration of SAR (structure-activity relationship). In addition, inhibitory effects of cell proliferation are evaluated against human cancer cell lines (NCI-H23 and PC-3).

Yakhak Hoechi 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 C15H10O2, HPLC of Formula: 56-05-3.

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