Day: November 21, 2022

Kovackova, Sona published the artcileThe synthesis of piperidine nucleoside analogs-a comparison of several methods to access the introduction of nucleobases, Formula: C4H3Cl2N3, the publication is Tetrahedron (2011), 67(7), 1485-1500, database is CAplus.

This work deals with the synthesis of piperidine and hydroxypiperidine analogs of nucleosides, e.g. I. Starting from com. available 3-hydroxypiperidine, proline or 4-hydroxyproline, a series of piperidine derivatives of both purine and pyrimidine nucleobases was prepared Various methods of nucleobase attachment were evaluated. The prepared compounds were tested for cytostatic, antibacterial, and antiviral properties but no significant activity was found.

Tetrahedron 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, Formula: C4H3Cl2N3.

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

Feuerstein, Marie published the artcileSonogashira reaction of heteroaryl halides with alkynes catalyzed by a palladium-tetraphosphine complex, SDS of cas: 174456-28-1, the publication is Journal of Molecular Catalysis A: Chemical (2006), 256(1-2), 75-84, database is CAplus.

Cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/(1/2)[PdCl(C₃H₅)]₂ system catalyzes the Sonogashira reaction of heteroaryl halides with a range of alkynes with moderate to high substrate/catalyst ratios in good yields. A variety of heteroaryl halides such as pyridines, quinolines, a pyrimidine, an indole, thiophenes, or a thiazole have been used successfully. The reaction also tolerates several alkynes such as phenylacetylene and alk-1-ynols. The nature of the heteroaromatics and the substituent of the alkynes have both an important effect on the reaction rates. High reaction rates were generally observed with phenylacetylene. With this alkyne substrate/catalyst ratios up to 10,000 have been used successfully. An effect of the position of the alc. function on the reaction rates was observed with alk-1-ynols. Higher substrate/catalyst ratios could be used with but-3-yn-1-ol, pent-4-yn-1-ol or hex-5-yn-1-ol than with propargyl alc. The nature and the position of the halide on the heteroaromatics have also an important effect on the reaction rates. As expected, higher reaction rates were obtained with heteroaryl iodides than with heteroaryl bromides or chlorides.

Journal of Molecular Catalysis A: Chemical published new progress about 174456-28-1. 174456-28-1 belongs to pyrimidines, auxiliary class Pyrimidine,Alkynyl,Alcohol, name is 3-(Pyrimidin-5-yl)prop-2-yn-1-ol, and the molecular formula is C7H6N2O, SDS of cas: 174456-28-1.

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

Ascencao, Kelly published the artcilePharmacological induction of mesenchymal-epithelial transition via inhibition of H₂S biosynthesis and consequent suppression of ACLY activity in colon cancer cells, Name: 6-Methyl-2-((2-(naphthalen-1-yl)-2-oxoethyl)thio)pyrimidin-4(3H)-one, the publication is Pharmacological Research (2021), 105393, database is CAplus and MEDLINE.

Hydrogen sulfide (H₂S) is an important endogenous gaseous transmitter mediator, which regulates a variety of cellular functions in autocrine and paracrine manner. The enzymes responsible for the biol. generation of H₂S include cystathionine-β-synthase (CBS), cystathionine-γ-lyase (CSE) and 3-mercaptopyruvate sulfurtransferase (3-MST). Increased expression of these enzymes and overproduction of H₂S has been implicated in essential processes of various cancer cells, including the stimulation of metabolism, maintenance of cell proliferation and cytoprotection. Cancer cell identity is characterized by so-called “transition states”. The progression from normal (epithelial) to transformed (mesenchymal) state is termed epithelial-to-mesenchymal transition (EMT) whereby epithelial cells lose their cell-to-cell adhesion capacity and gain mesenchymal characteristics. The transition process can also proceed in the opposite direction, and this process is termed mesenchymal-to-epithelial transition (MET). The current project was designed to determine whether inhibition of endogenous H₂S production in colon cancer cells affects the EMT/MET balance in vitro. Inhibition of H₂S biosynthesis in HCT116 human colon cancer cells was achieved either with aminooxyacetic acid (AOAA) or 2-[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]-1-(naphthalen-1-yl)ethan-1-one (HMPSNE). These inhibitors induced an upregulation of E-cadherin and Zonula occludens-1 (ZO-1) expression and downregulation of fibronectin expression, demonstrating that H₂S biosynthesis inhibitors can produce a pharmacol. induction of MET in colon cancer cells. These actions were functionally reflected in an inhibition of cell migration, as demonstrated in an in vitro “scratch wound” assay. The mechanisms involved in the action of endogenously produced H₂S in cancer cells in promoting (or maintaining) EMT (or tonically inhibiting MET) relate, at least in part, in the induction of ATP citrate lyase (ACLY) protein expression, which occurs via upregulation of ACLY mRNA (via activation of the ACLY promoter). ACLY in turn, regulates the Wnt-β-catenin pathway, an essential regulator of the EMT/MET balance. Taken together, pharmacol. inhibition of endogenous H₂S biosynthesis in cancer cells induces MET. We hypothesize that this may contribute to anti-cancer / anti-metastatic effects of H₂S biosynthesis inhibitors.

Pharmacological Research 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, Name: 6-Methyl-2-((2-(naphthalen-1-yl)-2-oxoethyl)thio)pyrimidin-4(3H)-one.

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

Prakash, Anjanappa published the artcileEfficient indoles and anilines syntheses employing tert-butyl sulfinamide as ammonia surrogate, Application of 5-Aminopyrimidine-2-carbonitrile, the publication is Tetrahedron Letters (2011), 52(43), 5625-5628, database is CAplus.

Tert-Bu sulfinamide is an ammonia equivalent for the palladium-catalyzed amination of aryl bromides and aryl chlorides. Using these amine derivatives, it has been observed that substituted indoles and anilines with sensitive functional groups can be readily prepared This surrogate has also been used for the synthesis of indoles from (2-bromophenyl)ethynes using palladium-catalyzed cross coupling reaction as the key step.

Tetrahedron Letters 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, Application of 5-Aminopyrimidine-2-carbonitrile.

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

Bowler, Frank R. published the artcileDNA Analysis by Dynamic Chemistry, Name: 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 Angewandte Chemie, International Edition (2010), 49(10), 1809-1812, S1809/1-S1809/29, database is CAplus and MEDLINE.

Herein we report the application of dynamic chem. to DNA anal., offering the prospect of nonenzymic genotyping of genomic DNA amplified by polymerase chain reaction (PCR). This was achieved by the synthesis of a PNA strand that contained a blank position opposite the nucleobase under anal. in a complementary DNA template. A reversible reaction, between this PNA/DNA duplex (specifically the secondary amine of the “PNA blank”) and four aldehyde-modified nucleobases, means that the templating power of Watson-Crick base pairing and base stacking would be expected to drive the selection of the fully complementary iminium nucleobase. Subsequent reduction and MALDI-TOF mass spectrometry would allow rapid determination of base incorporation.

Angewandte Chemie, International Edition 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, Name: 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

Das, Indrajit published the artcileA Peptide Nucleic Acid-Amino-Sugar Conjugate Targeting Transactivation Response Element of HIV-1 RNA Genome Shows a High Bioavailability in Human Cells and Strongly Inhibits Tat-Mediated Transactivation of HIV-1 Transcription, Application 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 Journal of Medicinal Chemistry (2012), 55(13), 6021-6032, database is CAplus and MEDLINE.

The 6-aminoglucosamine ring of the aminoglycoside antibiotic neomycin B (ring II) was conjugated to a 16-mer peptide nucleic acid (PNA) targeting HIV-1 TAR RNA. For this purpose, we prepared the aminoglucosamine monomer I and attached it to the protected PNA prior to its cleavage from the solid support. We found that the resulting PNA-aminoglucosamine conjugate is stable under acidic conditions, efficiently taken up by the human cells and fairly distributed in both cytosol and nucleus without endosomal entrapment because co-treatment with endosome-disrupting agent had no effect on its cellular distribution. The conjugate displayed very high target specificity in vitro and strongly inhibited Tat mediated transactivation of HIV-1 LTR transcription in a cell culture system. The unique properties of this new class of PNA conjugate suggest it to be a potential candidate for therapeutic application.

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 C39H35N5O8, Application 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

Das, Indrajit published the artcileA Peptide Nucleic Acid-Amino-Sugar Conjugate Targeting Transactivation Response Element of HIV-1 RNA Genome Shows a High Bioavailability in Human Cells and Strongly Inhibits Tat-Mediated Transactivation of HIV-1 Transcription, Category: pyrimidines, the publication is Journal of Medicinal Chemistry (2012), 55(13), 6021-6032, database is CAplus and MEDLINE.

The 6-aminoglucosamine ring of the aminoglycoside antibiotic neomycin B (ring II) was conjugated to a 16-mer peptide nucleic acid (PNA) targeting HIV-1 TAR RNA. For this purpose, we prepared the aminoglucosamine monomer I and attached it to the protected PNA prior to its cleavage from the solid support. We found that the resulting PNA-aminoglucosamine conjugate is stable under acidic conditions, efficiently taken up by the human cells and fairly distributed in both cytosol and nucleus without endosomal entrapment because co-treatment with endosome-disrupting agent had no effect on its cellular distribution. The conjugate displayed very high target specificity in vitro and strongly inhibited Tat mediated transactivation of HIV-1 LTR transcription in a cell culture system. The unique properties of this new class of PNA conjugate suggest it to be a potential candidate for therapeutic application.

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 C26H26N4O7, Category: pyrimidines.

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

Ptasinska, Sylwia published the artcileBond- and site-selective loss of H atoms from nucleobases by very-low-energy electrons (< 3 eV), Formula: C5H6N2O2, the publication is Angewandte Chemie, International Edition (2005), 44(42), 6941-6943, database is CAplus and MEDLINE.

When excess charge is deposited on thymine and uracil by resonant attachment of low-energy electrons (0-3 eV), H atoms are cleaved exclusively from the N positions. This bond selectivity can be made site selective (N1 vs. N3 position) by properly tuning the electron energy. This conclusion was drawn from experiments with methylated thymine and uracil (see picture) in crossed beam experiments

Angewandte Chemie, International Edition 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, Formula: C5H6N2O2.

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

Ptasinska, Sylwia published the artcileBond- and Site-Selective Loss of H^– from Pyrimidine Bases, Application In Synthesis of 608-34-4, the publication is Physical Review Letters (2005), 95(9), 093201/1-093201/4, database is CAplus and MEDLINE.

Electron attachment to gas phase thymine and uracil leads to H^– loss within a broad and structured feature in the energy range between about 5 and 12 eV consisting of 4 overlapping resonances. By using thymine and uracil methylated at the N1 and N3 positions, resp., and taking into account recent results from partly deuterated thymine, we find that by tuning the electron energy, H^– loss turns out to be not only bond selective, i.e., (C-H) vs. (N-H) bonds, but also site selective (N1 vs. N3 site). Such a bond and site selectivity by energy has not been observed before in dissociative electron attachment. Implications for the mechanism of strand breaks observed in plasmid DNA are considered.

Physical Review 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

Alguacil, Javier published the artcileA Straightforward Preparation of Aminoglycoside-Dinucleotide and -diPNA Conjugates via Click Ligation Assisted by Microwaves, Synthetic Route of 169396-92-3, the publication is European Journal of Organic Chemistry (2010), 3102-3109, S3102/1-S3102/30, database is CAplus.

An alternative and straightforward method to prepare aminoglycoside-dinucleotide and -diPNA conjugates is reported, which is based on copper-catalyzed Huisgen azide-alkyne cycloaddition (“click chem.” ligation) assisted by microwave irradiation This method permitted conjugations to be performed in aqueous solution, in very short times and with readily prepared precursors.

European 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, Synthetic Route of 169396-92-3.

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