Category: pyrimidines

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

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

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

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

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

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

Sun, Chang-Zheng published the artcileCharacterization of the doxorubicin-pluronic F68 conjugate micelles and their effect on doxorubicin resistant human erythroleukemic cancer cells, Recommanded Product: N,N-Dimethylpyrimidin-4-amine, the publication is Journal of Nanomedicine & Nanotechnology (2011), 2(5), 1000114, database is CAplus.

Doxorubicin-pluronic F68 conjugate (DOX-P) was synthesized and its structure was confirmed by FTIR and H-NMR spectra. Using human erythroleukemic cancer cells as model, DOX-P application in chemotherapy was further investigated. Differential scanning calorimetry anal. was applied to compare the fusion and crystallization characterization between pluronic F68 and DOX-P. Morphol. and size assessment were measured using a transmission electron microscopy (TEM) to confirm the capability of forming micelles of DOX-P. Tumor cell lines K562 and K562/AO2 were used to investigate the effect of DOX-P on tumor cell resistance. The Tm and Tc of DOX-P were lower than pluronic F68 resulted from the connection of DOX to pluronic F68. Morphol. images confirmed the existence of DOX-P micelles, with an average size of about 20 nm. Drug release profile showed that the DOX-P conjugate maintained a sustained DOX release. From cell experiment in vitro, DOX-P micelles could circumvent the DOX resistance of K562/AO2 cells. With advantages of EPR effect and reducing tumor resistance, DOX-P micelles might develop as new tumor targeted delivery system for chemotherapy.

Journal of Nanomedicine & Nanotechnology 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 C7H5I2NO3, Recommanded Product: N,N-Dimethylpyrimidin-4-amine.

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

Gustin, Darin J. published the artcileIdentification of potent, noncovalent fatty acid amide hydrolase (FAAH) inhibitors, Name: 2-Amino-4,6-dichloropyrimidine, the publication is Bioorganic & Medicinal Chemistry Letters (2011), 21(8), 2492-2496, database is CAplus and MEDLINE.

Starting from a series of ureas that were determined to be mechanism-based inhibitors of FAAH, several spirocyclic ureas and lactams e. g., I were designed and synthesized. These efforts identified a series of novel, noncovalent FAAH inhibitors with in vitro potency comparable to known covalent FAAH inhibitors. The mechanism of action for these compounds was determined through a combination of SAR and co-crystallog. with rat FAAH.

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, Name: 2-Amino-4,6-dichloropyrimidine.

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

Bhingardeve, Pramod published the artcileReceptor-Specific Delivery of Peptide Nucleic Acids Conjugated to Three Sequentially Linked N-Acetyl Galactosamine Moieties into Hepatocytes, 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 Journal of Organic Chemistry (2020), 85(14), 8812-8824, database is CAplus and MEDLINE.

Peptide nucleic acids (PNAs) are DNA analogs that bind with high affinity to DNA and RNA in a sequence-specific manner but have poor cell permeability, limiting use as therapeutic agents. The work described here is motivated by recent reports of efficient gene silencing specifically in hepatocytes by small interfering RNAs conjugated to triantennary N-acetyl galactosamine (GalNAc), the ligand recognized by the asialoglycoprotein receptor (ASGPR). PNAs conjugated to either triantennary GalNAc at the N-terminus (the branched architecture) or monomeric GalNAc moieties anchored at C^γ of three consecutive PNA monomers of N-(2-aminoethyl)glycine (aeg) scaffolds (the sequential architecture) were synthesized on the solid phase. These formed duplexes with complementary DNA and RNA as shown by UV and CD spectroscopy. The fluorescently labeled analogs of GalNAc-conjugated PNAs were internalized by HepG2 cells that express the ASGPR but were not taken up by HEK-293 cells that lack this receptor. The sequential conjugate was internalized about 13-fold more efficiently than the branched conjugate into HepG2 cells, as demonstrated by confocal microscopy. The results presented here highlight the potential significance of the architecture of GalNAc conjugation for efficient uptake by target liver cells and indicate that GalNAc-conjugated PNAs have possible therapeutic applications.

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, 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

Lemoine, Remy C. published the artcileSynthesis of base-modified dihydropacidamycins, Application In Synthesis of 608-34-4, the publication is Bioorganic & Medicinal Chemistry Letters (2002), 12(7), 1121-1123, database is CAplus and MEDLINE.

The authors describe the synthesis of 1,2-di-O-acetyl-5-azido-3,5-dideoxy-α,β-L-arabinofuranose, a carbohydrate donor that was used for the synthesis of 1-(5′-amino-3′,5′-dideoxy-α-L-arabinofuranosyl)uracil, the nucleoside found in dihydropacidamycin D. The carbohydrate donor was also used for the synthesis of a set of new nucleosides that were introduced in new dihydropacidamycins. These compounds were tested for biol. activity, and the results showed that uracil is the only base recognized by MraY.

Bioorganic & Medicinal Chemistry 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 In Synthesis of 608-34-4.

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