Day: November 25, 2022

Huang, Xian published the artcileSolid-Phase Synthesis of 4(1H)-Quinolone and Pyrimidine Derivatives Based on a New Scaffold-Polymer-Bound Cyclic Malonic Acid Ester, Computed Properties of 608-34-4, the publication is Journal of Organic Chemistry (2002), 67(19), 6731-6737, database is CAplus and MEDLINE.

An efficient method for the preparation of polymer-bound cyclic malonic acid ester starting from Merrifield resin has been developed. Reaction of the resin-bound cyclic malonic acid ester with tri-Et orthoformate and subsequent double substitution with nucleophilic reagents, such as arylamine, urea, thiourea, 2-aminobenzothiazoles, or isothiosemicarbazones, afforded the corresponding polymer-bound substituted aminomethylene cyclic malonic acid esters, which upon thermal treatment led to 4(1H)-quinolones, 3-substituted uracils and thiouracils, 4H-pyrimido[2,1-b]benzothiazol-4-ones, and 1-(N-alkylidene or benzylideneamino)-1,6-dihydro-2-methylthio-6-oxo-pyrimidines, depending on the structures of the nucleophilic reagents.

Journal of 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, Computed Properties of 608-34-4.

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

Li, Shasha published the artcileSolubility Measurement and Modeling of 2-Amino-4,6-dichloropyrimidine in Ten Pure Solvents and (Ethyl Acetate + Ethanol) Solvent Mixtures, Synthetic Route of 56-05-3, the publication is Journal of Chemical & Engineering Data (2018), 63(10), 3715-3726, database is CAplus.

The basis of purification and further theor. studies of 2-amino-4,6-dichloropyrimidine is the solubility and solution thermodn. in different solvents. In this paper, the solubility of 2-amino-4,6-dichloropyrimidine in 10 neat solvents (methanol, ethanol, n-propanol, isopropanol, acetone, acetonitrile, Et acetate, 1,4-dioxane, toluene, and cyclohexane) and binary liquid mixtures (Et acetate + ethanol) was measured by the isothermal saturation method at temperatures range from 278.15 to 318.15 K, at p = 101.2 kPa. High-performance liquid chromatog. (HPLC) was used to analyze the solubility of 2-amino-4,6-dichloropyrimidine in selected solvents. To sum up, the equilibrium mole fraction solubility was highest in 1,4-dioxane (2.619 × 10^-2 at 318.15 K) and lowest in cyclohexane (0.02238 × 10^-2 at 318.15 K), and ranked as 1,4-dioxane (2.619 × 10^-2 at 318.15 K) > acetone (1.630 × 10^-2 at 318.15 K) > Et acetate (1.471 × 10^-2 at 318.15 K) > acetonitrile (0.5048 × 10^-2 at 318.15 K) > methanol (0.3888 × 10^-2 at 318.15 K) > ethanol (0.3391 × 10^-2 at 318.15 K) > n-propanol (0.3133 × 10^-2 at 318.15 K) > toluene (0.2737 × 10^-2 at 318.15 K) > isopropanol (0.2574 × 10^-2 at 318.15 K) > cyclohexane (0.02238 × 10^-2 at 318.15 K). The achieved solubility values in monosolvents were correlated by the modified Apelblat equation, λh equation, Wilson model, and NRTL model and in solvent mixtures by three cosolvency models including Jouyban-Acree model, van’t Hoff-Jouyban-Acree model, and Apelblat-Jouyban-Acree model. Calculated results fitted well with exptl. data. Consequently, for the monosolvents, the values of root-mean-square deviation (RMSD) and relative average deviation (RAD) were less than 0.58 × 10^-4 and 0.80%, resp., and for the binary solvent mixtures were 0.49 × 10^-4 and 0.46%. Furthermore, the Gibbs energy, mixing enthalpy, mixing entropy, activity coefficient at infinitesimal concentration (γ^∞₁) and reduced excess enthalpy (H^E,∞₁) in monosolvents, and dissolution property in mixed solvents were computed. The mixing process of 2-amino-4,6-dichloropyrimidine in the studied solvents was spontaneous and endothermic. The obtained solubility and thermodn. studies would be used to optimize the purification process of 2-amino-4,6-dichloropyrimidine.

Journal of Chemical & Engineering Data 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, Synthetic Route of 56-05-3.

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

Chen, Xuwang published the artcileNovel piperidinylamino-diarylpyrimidine derivatives with dual structural conformations as potent HIV-1 non-nucleoside reverse transcriptase inhibitors, HPLC of Formula: 56-05-3, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(24), 6593-6597, database is CAplus and MEDLINE.

A series of novel piperidinylamino-diarylpyrimidine (pDAPY) derivatives with dual structural conformations was designed through a mol. hybridization strategy and expected to bind into the non-nucleoside inhibitor binding pocket (NNIBP) of HIV-1 RT in a flexible manner. A cell-based antiviral screening assay showed that some compounds were active against both wild-type and drug-resistant mutant virus strains (K103N+Y181C RT) of HIV-1, (4-(2-(4-cyanophenylamino)-6-(1-(pyridin-4-yl-methyl)piperidin-4-yl-amino)pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile with EC₅₀ = 0.047 and 4.6 μM, selectivity index = 2145 and 22, resp.). Mol. simulation studies indicated that 4-(2-(4-cyanophenylamino)-6-(1-(pyridin-4-yl-methyl)piperidin-4-ylamino)pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile could maintain the key hydrophobic interaction and hydrogen bonds with the NNIBP of two RT/ligand complexes. In particular, it could simultaneously occupy the protein/solvent interface and the entrance channel. Exploring these hybrid mols. with dual binding conformations might provide optional chem. scaffolds as novel HIV-1 reverse transcriptase inhibitors (HIV-1 NNRTIs).

Bioorganic & Medicinal Chemistry 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, HPLC of Formula: 56-05-3.

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

Soukarieh, Fadi published the artcileHit identification of new potent PqsR antagonists as inhibitors of quorum sensing in planktonic and biofilm grown Pseudomonas aeruginosa, HPLC of Formula: 105130-26-5, the publication is Frontiers in Chemistry (Lausanne, Switzerland) (2020), 00204, database is CAplus and MEDLINE.

Current treatments for Pseudomonas aeruginosa infections are becoming less effective because of the increasing rates of multi-antibiotic resistance. Pharmacol. targeting of virulence through inhibition of quorum sensing (QS) dependent virulence gene regulation has considerable therapeutic potential. In P. aeruginosa, the pqs QS system regulates the production of multiple virulence factors as well as biofilm maturation and is a promising approach for developing antimicrobial adjuvants for combating drug resistance. In this work, we report the hit optimization for a series of potent novel inhibitors of PqsR, a key regulator of the pqs system, bearing a 2-((5-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)thio) acetamide scaffold. The initial hit compound 7 (PAO1-L IC₅₀ 0.98 ± 0.02 μM, PA14 inactive at 10 μM) was obtained through a virtual screening campaign performed on the PqsR ligand binding domain using the University of Nottingham Managed Chem. Compound Collection. Hit optimization gave compounds with enhanced potency against strains PAO1-L and PA14, evaluated using P. aeruginosa pqs-based QS bioreporter assays. Compound 40 (PAO1-L IC₅₀ 0.25 ± 0.12 μM, PA14 IC₅₀ 0.34 ± 0.03 μM) is one of the most potent PqsR antagonists reported showing significant inhibition of P. aeruginosa pyocyanin production and pqs system signaling in both planktonic cultures and biofilms. The co-crystal structure of 40 with the PqsR ligand binding domain revealed the specific binding interactions occurring between inhibitor and this key regulatory protein.

Frontiers in Chemistry (Lausanne, Switzerland) published new progress about 105130-26-5. 105130-26-5 belongs to pyrimidines, auxiliary class Pyrimidine,Amine,Benzene,Ether, name is 4-(2-Pyrimidinyloxy)aniline, and the molecular formula is C10H20O2, HPLC of Formula: 105130-26-5.

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

Lin, Cui-Hua published the artcile2-Amino-4,6-dimethoxypyrimidin-1-ium 2,2-dichloroacetate, Product Details of C4H3Cl2N3, the publication is Acta Crystallographica, Section E: Structure Reports Online (2012), 68(6), o1898, database is CAplus and MEDLINE.

In the title salt, C₆H₁₀N₃O₂⁺·C₂HCl₂O₂^–, two cations and two anions are linked by N-H···O hydrogen bonds, forming chains along the c axis. Crystallog. data are given.

Acta Crystallographica, Section E: Structure Reports Online 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, Product Details of C4H3Cl2N3.

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

Qiu, Bo published the artcileQuintets of uracil and thymine: a novel structure of nucleobase self-assembly studied by electrospray ionization mass spectrometry, Name: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Chemical Communications (Cambridge, United Kingdom) (2009), 2863-2865, database is CAplus and MEDLINE.

ESI-MS and mol. dynamic calculations reveal that in the presence of K⁺, Rb⁺ and Cs⁺, uracil, thymine and their homologs form self-assembled quintet structures that are stabilized by hydrogen bonding and ion dipole interactions.

Chemical Communications (Cambridge, United Kingdom) 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, Name: 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Heemstra, Jennifer M. published the artcileTemplated Synthesis of Peptide Nucleic Acids via Sequence-Selective Base-Filling Reactions, Formula: C39H35N5O8, the publication is Journal of the American Chemical Society (2009), 131(32), 11347-11349, database is CAplus and MEDLINE.

The templated synthesis of nucleic acids has previously been achieved through the backbone ligation of preformed nucleotide monomers or oligomers. In contrast, the authors, here, demonstrate templated nucleic acid synthesis using a base-filling approach in which individual bases are added to abasic sites of a peptide nucleic acid (PNA). Because nucleobase substrates in this approach are not self-reactive, a base-filling approach may reduce the formation of non-templated reaction products. Using either reductive amination or amine acylation chemistries, the authors observed efficient and selective addition of each of the four nucleobases to an abasic site in the middle of the PNA strand. The authors also describe the addition of single nucleobases to the end of a PNA strand through base filling, as well as the tandem addition of two bases to the middle of the PNA strand. These findings represent an exptl. foundation for nonenzymic information transfer through base filling.

Journal of the American Chemical Society 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, Formula: C39H35N5O8.

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

Lores Lareo, Pablo published the artcileNucleic acid and SNP detection via template-directed native chemical ligation and inductively coupled plasma mass spectrometry, COA of Formula: C39H35N5O8, the publication is Journal of Mass Spectrometry (2019), 54(8), 676-683, database is CAplus and MEDLINE.

Detection of nucleic acids and single nucleotide polymorphisms (SNPs) is of pivotal importance in biol. and medicine. Given that the biol. effect of SNPs often is enhanced in combination with other SNPs, multiplexed SNP detection is desirable. We show proof of concept of the multiplexed detection of SNPs based on the template-directed native chem. ligation (NCL) of PNA-probes carrying a metal tag allowing detection using ICP-MS. For the detection of ssDNA oligonucleotides (30 bases), two probes, one carrying the metal tag and a second one carrying biotin for purification, are covalently ligated. The methodol. limit of detection is of 29 pM with RSD of 6.7% at 50 pM (n = 5). Detection of SNPs is performed with the combination of two sets of reporter probes. The first probe set targets the SNP, and its yield is compared with a second set of probes targeting a neighboring sequence. The assay was used to simultaneously differentiate between alleles of three SNPs at 5-nM concentration

Journal of Mass Spectrometry 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, COA of Formula: C39H35N5O8.

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

Lores Lareo, Pablo published the artcileNucleic acid and SNP detection via template-directed native chemical ligation and inductively coupled plasma mass spectrometry, Product Details of C26H26N4O7, the publication is Journal of Mass Spectrometry (2019), 54(8), 676-683, database is CAplus and MEDLINE.

Detection of nucleic acids and single nucleotide polymorphisms (SNPs) is of pivotal importance in biol. and medicine. Given that the biol. effect of SNPs often is enhanced in combination with other SNPs, multiplexed SNP detection is desirable. We show proof of concept of the multiplexed detection of SNPs based on the template-directed native chem. ligation (NCL) of PNA-probes carrying a metal tag allowing detection using ICP-MS. For the detection of ssDNA oligonucleotides (30 bases), two probes, one carrying the metal tag and a second one carrying biotin for purification, are covalently ligated. The methodol. limit of detection is of 29 pM with RSD of 6.7% at 50 pM (n = 5). Detection of SNPs is performed with the combination of two sets of reporter probes. The first probe set targets the SNP, and its yield is compared with a second set of probes targeting a neighboring sequence. The assay was used to simultaneously differentiate between alleles of three SNPs at 5-nM concentration

Journal of Mass Spectrometry 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, Product Details of C26H26N4O7.

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

Li, Nan published the artcileCopper-Free Sonogashira Cross-Coupling for Functionalization of Alkyne-Encoded Proteins in Aqueous Medium and in Bacterial Cells, Synthetic Route of 5738-14-7, the publication is Journal of the American Chemical Society (2011), 133(39), 15316-15319, database is CAplus and MEDLINE.

Bioorthogonal reactions suitable for functionalization of genetically or metabolically encoded alkynes, for example, copper-catalyzed azide-alkyne cycloaddition reaction (“click chem.”), have provided chem. tools to study biomol. dynamics and function in living systems. Despite its prominence in organic synthesis, copper-free Sonogashira cross-coupling reaction suitable for biol. applications has not been reported. In this work, the authors report the discovery of a robust aminopyrimidine-palladium(II) complex for copper-free Sonogashira cross-coupling that enables selective functionalization of a homopropargylglycine (HPG)-encoded ubiquitin protein in aqueous medium. A wide range of aromatic groups including fluorophores and fluorinated aromatic compounds can be readily introduced into the HPG-containing ubiquitin under mild conditions with good to excellent yields. The suitability of this reaction for functionalization of HPG-encoded ubiquitin in Escherichia coli was also demonstrated. The high efficiency of this new catalytic system should greatly enhance the utility of Sonogashira cross-coupling in bioorthogonal chem.

Journal of the American Chemical Society 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 C6H9N3O2, Synthetic Route of 5738-14-7.

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