Category: pyrimidines

Nokihara, Kiyoshi published the artcileImproved coupling methods for the difficult amide-bond formation in solid-phase assembly, Quality Control of 186046-81-1, the publication is Peptide Science (2013), 167-170, database is CAplus.

A symposium report. In the solid-phase peptide synthesis certain peptides are difficult to assemble because of steric hindrance and aggregation of mols., more over in such case removal of Nα-Fmoc group (Fmoc = 9-fluorenylmethoxycarbonyl) is also hindered. Yield and purity of desired peptides after cleavage are important for economical aspects, especially amide bond formation with costly unnatural amino acids as building blocks. The present report describes amide bond formation by elevated temperature to overcome poor coupling efficiency and to realize shorter coupling times. Addnl. racemization during Fmoc-removal at elevated temperature is also investigated.

Peptide Science 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, Quality Control of 186046-81-1.

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

Zielenkiewicz, W. published the artcilePartial molar volumes of alkylated uracils- insight into the solvation shell? Part II, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of Solution Chemistry (1998), 27(6), 543-551, database is CAplus.

The solute-solvent interactions in aqueous solutions of alkylated uracils are discussed. The partial molar volume data are interpreted using a new model of interaction of the solute mol. with the solvent. The model is based on the assumption that the d. of solvent in the hydration shell depends on the structure and polarity of the solute mol. The relation among mol. volume, partial molar volume, and volume of the solvation shell is expressed by α parameter, which is defined as the relative d. of the solvation shell. It is found that in compounds with the same number of CH₂– groups, the α values depend on substitution on the C or N atoms of the uracil skeleton. The α values also depend to some extent, on screening of the oxygen atoms by methylation of the neighboring atoms of the uracil ring. A correlation is presented between the relative d. of solvation shell and polarity (defined as the ratio of the surface of polar groups and atoms exposed to the solvent to the total accessible mol. surface of the mol.) for the compounds studied. It was demonstrated that of the various solute-solvent interactions the dominant role is played by polar interactions.

Journal of Solution 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 C5H7BO2S, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Litonska, Ewa published the artcileConformation of the dimethylamino group in cytosine and in simple model pyrimidines and pyridines. Steric effects of ortho-methyl substitution on infrared spectra and molecular dipole moments, Product Details of C6H9N3, the publication is Acta Biochimica Polonica (1979), 26(1-2), 39-54, database is CAplus.

The IR of NR₂ (R = H, Me) derivatives of 4- or 5-substituted pyrimidines, 4-substituted pyridines, benzenes, or the resp. cytosines were determined in the skeletal ring vibration region. The sensitivity of the ring vibrations, at âˆ?600 cm^-1, to electron donating groups is used to determine the o-Me group as the steric hindrance of NMe₂ conjugation with the ring. The dipole moments of simple pyrimidine and pyridine derivatives were determined in C₆H₆. The vectorial anal. of the dipole moments indicates that the twisting of the Me₂N group in the hindered derivatives decreases in the order: 5-dimethylaminopyrimidine > 4-dimethylaminopyridine > 4-dimethylaminopyrimidine. Sterically crowded I is planar.

Acta Biochimica Polonica 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 C6H9N3, Product Details of C6H9N3.

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

Patel, Navin B. published the artcileNew 2-benzylsulfanyl-nicotinic acid based 1,3,4-oxadiazoles: Their synthesis and biological evaluation, Synthetic Route of 56-05-3, the publication is European Journal of Medicinal Chemistry (2013), 677-687, database is CAplus and MEDLINE.

A novel series of 5-(2-benzylsulfanyl-pyridin-3-yl)-2-(substituted)-sulfanyl-1,3,4-oxadiazoles were synthesized from key intermediate 5-(2-benzylsulfanyl-pyridin-3-yl)-3H-[1,3,4]oxadiazole-2-thione. Nucleophilic substitution reactions with different electrophiles (E+), such as haloacetate and haloalkyl groups, were performed to get target compounds Compounds were characterized by NMR, mass, IR spectra and C, H, N analyses. All compounds were evaluated for their antimicrobial and antimycobacterial activities; selected analogs were screened for their anticancer activity on 60 tumor cell lines at single dose 1.00^-5 M. Unfortunately, none of the compounds showed a significant antitumor activity on 60 human tumor cell lines. However, compounds I and II with benzothiazole moiety (12.5 and 25 μg/mL) showed promising activity against Escherichia coli compared to ampicillin; compounds III, IV bearing triazole and morpholine, resp., showed promising antitubercular activity (25 μg/mL) compared to rifampicin.

European 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, Synthetic Route of 56-05-3.

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

Willwacher, Jens published the artcileSelective Metal-Site-Guided Arylation of Proteins, Category: pyrimidines, the publication is Journal of the American Chemical Society (2016), 138(28), 8678-8681, database is CAplus and MEDLINE.

We describe palladium-mediated S-arylation that exploits natural metal-binding motifs to ensure high site selectivity for a proximal reactive residue. This allows the chem. identification not only of proteins that bind metals but also the environment of the metal-binding site itself through proteomic anal. of arylation sites. The transformation is easy to perform under standard conditions, does not require the isolation of a reactive Ar-Pd complex, is broad in scope, and is applicable in cell lysates as well as to covalent inhibition/modulation of metal-dependent enzymic activity.

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 C6H13I, Category: pyrimidines.

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

Li, Nan published the artcileA Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface, Name: 2-(Dimethylamino)pyrimidine-4,6-diol, the publication is ACS Chemical Biology (2015), 10(2), 379-384, database is CAplus and MEDLINE.

The merging of site-specific incorporation of small bioorthogonal functional groups into proteins via amber codon suppression with bioorthogonal chem. has created exciting opportunities to extend the power of organic reactions to living systems. A new alkyne amino acid can be site-selectively incorporated into mammalian proteins via a known orthogonal pyrrolysyl-tRNA synthetase/tRNA_CUA pair and directs an unprecedented, palladium-mediated cross-coupling reaction-driven protein labeling on live mammalian cell surface. A comparison study with the alkyne-encoded proteins in vitro indicated that this terminal alkyne is better suited for the palladium-mediated cross-coupling reaction than the copper-catalyzed click chem.

ACS Chemical Biology 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, Name: 2-(Dimethylamino)pyrimidine-4,6-diol.

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

Augsburger, Fiona published the artcileRole of 3-mercaptopyruvate sulfurtransferase in the regulation of proliferation, migration, and bioenergetics in murine colon cancer cells, Category: pyrimidines, the publication is Biomolecules (2020), 10(3), 447, database is CAplus and MEDLINE.

The current study was designed to investigate the functional role of 3-MST’s catalytic activity in the murine colon cancer cell line CT26. The novel pharmacol. 3-MST inhibitor HMPSNE was used to assess cancer cell proliferation, migration and bioenergetics in vitro. Methods included measurements of cell viability (MTT and LDH assays), cell proliferation and in vitro wound healing (IncuCyte) and cellular bioenergetics (Seahorse extracellular flux anal.). 3-MST expression was detected by Western blotting; H₂S production was measured by the fluorescent dye AzMC. The results show that CT26 cells express 3-MST protein and mRNA, as well as several enzymes involved in H₂S degradation (TST, ETHE1). HMPSNE exerted a bell-shaped effect on several cellular bioenergetic parameters related to oxidative phosphorylation, while other bioenergeticparameterswereeitherunaffectedorinhibitedatthehighestconcentrationoftheinhibitor tested (300μM). In contrast to 3-MST, the expression of CBS (another H₂S producing enzyme which has been previously implicated in the regulation of various biol. parameters in other tumor cells) was not detectable in CT26 cells and pharmacol. inhibition of CBS exerted no significant effects on CT26 proliferation or bioenergetics. In summary, 3-MST catalytic activity significantly contributes to the regulation of cellular proliferation, migration and bioenergetics in CT26 murine colon cancer cells.

Biomolecules published new progress about 459420-09-8. 459420-09-8 belongs to pyrimidines, auxiliary class Metabolic Enzyme,3MST, name is 6-Methyl-2-((2-(naphthalen-1-yl)-2-oxoethyl)thio)pyrimidin-4(3H)-one, and the molecular formula is C17H14N2O2S, Category: pyrimidines.

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

Rajasekaran, S. published the artcileSynthesis and anti-denaturation activity of some substituted quinazolinone analogs, Safety of 2-Amino-4,6-dichloropyrimidine, the publication is International Journal of ChemTech Research (2012), 4(3), 1207-1211, database is CAplus.

In recent years there is a tremendous increase of inflammatory cases, leading to the design and development of newer anti-inflammatory agents. The reaction of 2-substituted phenyl-3-chloroacetamido quinazolin-4(3H)-ones with various 5-phenyl-1,3,4-oxadiazole-2-thiol and 5-(pyridine-4-yl)-1,3,4-oxadiazole-2-thiol gave N-(4-oxo-2-substituted phenylquinazolin-3(4H)-yl)-2-[(5-aryl-1,3,4-oxadiazol-2-yl)sulfanyl] acetamides derivatives The reaction of 2-phenyl-3-chloroacetamido quinazolinone with various heteroaryl thiols and amines gave N-(4-oxo-2-Ph quinazolin-3(4H)-yl)-2-[(substituted amino/thiol)] acetamide derivatives The structure of all the compounds has been confirmed by IR, ¹HNMR, Mass spectral data and elemental anal. In vitro anti-inflammatory activity was performed by bovine serum albumin method. Some of the compounds have shown good antibacterial activity and few have shown moderate antioxidant activity compared to the standard drug.

International Journal of ChemTech Research 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, Safety of 2-Amino-4,6-dichloropyrimidine.

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

Kheria, Sanjeev published the artcileThree in one: prototropy-free highly stable AADD-type self-complementary quadruple hydrogen-bonded molecular duplexes with a built-in fluorophore, Application In Synthesis of 56-05-3, the publication is Chemical Communications (Cambridge, United Kingdom) (2017), 53(18), 2689-2692, database is CAplus and MEDLINE.

This communication reports an effective approach for addressing the prototropy-related problems in heterocycle-based AADD-type self-assembling systems by freezing their hydrogen-bonding codes, by utilizing intramol. bifurcated hydrogen bonding interactions. Using this strategy, we have also developed a hydroquinone-conjugated AADD-type self-assembling system adorned with three valuable features such as prototropy-free dimerization yielding single duplexes, high duplex stability and a built-in fluorophore, which would augment its application potential. The rational approach used herein to arrest prototropic shift may also find application elsewhere, wherein proton shift-mediated structural changes become a detrimental factor.

Chemical Communications (Cambridge, United Kingdom) 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, Application In Synthesis of 56-05-3.

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

Sana, Sravani published the artcileExploration of carbamide derived pyrimidine-thioindole conjugates as potential VEGFR-2 inhibitors with anti-angiogenesis effect, Synthetic Route of 56-05-3, the publication is European Journal of Medicinal Chemistry (2020), 112457, database is CAplus and MEDLINE.

Here combined the two pharmacophoric units (pyrimidine and thioindole) combined in a single entity via mol. hybridization strategy along with introduction of urea functionality at C2 position of pyrimidine to increase the efficiency of H-bonding interactions. Among the synthesized conjugates I [R¹ = morpholino, piperidin-1-yl, phenylamino, etc.; R² = Ph, 4-methoxyphenyl, 4-chlorophenyl, etc.] compound I [R¹ = pyrrolidin-1-yl; R² = 4-chlorophenyl] was found to exhibited significant IC₅₀ =5.85, 7.87, 6.41 and 10.43μM against MDA-MB-231 (breast), HepG2 (liver), A549 (lung) and PC-3 (prostate) cancer cell lines, resp. All these compounds I were further evaluated for their inhibitory activities against VEGFR-2 protein. The results specified that among the tested compounds, I [R¹ = morpholino, R² = 2-methyl-4-chlorophenyl; R¹ = piperidin-1-yl, R² = 2,5-dimethylphenyl; R¹ = pyrrolidin-1-yl, R² = 4-chlorophenyl; R¹ = pyrrolidin-1-yl, R² = 2-methyl-4-chlorophenyl, R¹ = 4-(pyridin-2-yl)piperazin-1-yl, R² = 2-methyl-4-chlorophenyl; R¹ = 4-benzylpiperazin-1-yl, R² = Ph, 4-methoxyphenyl; R¹ = cyclopropylamino, R² = 2-methyl-4-chlorophenyl] prominently suppressed VEGFR-2, with IC₅₀ values of 310-920 nM in association to the pos. control (210 nM). Angiogenesis inhibition was evident by tube formation assay in HUVECs and cell-invasion by transwell assay. The mechanism of cellular toxicity on MDA-MB-231 was found through depolarization of mitochondrial membrane potential, increased ROS production and subsequent DNA damage resulting in apoptosis induction. Moreover, clonogenic and wound healing assays designated the inhibition of colony formation and cell migration by I [R¹ = pyrrolidin-1-yl; R² = 4-chlorophenyl] in a dose-dependent manner. Mol. docking studies also shown that compound I [R¹ = pyrrolidin-1-yl; R² = 4-chlorophenyl] capably intermingled with catalytically active residues GLU-885, ASP-1046 of the VEGFR-2 through hydrogen-bonding interactions.

European 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, Synthetic Route of 56-05-3.

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