Category: pyrimidines

Takagi, Kenji published the artcileSNP discrimination by tolane-modified peptide nucleic acids: application for the detection of drug resistance in pathogens, 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 Molecules (2020), 25(4), 769, database is CAplus and MEDLINE.

During the treatment of viral or bacterial infections, it is important to evaluate any resistance to the therapeutic agents used. An amino acid substitution arising from a single base mutation in a particular gene often causes drug resistance in pathogens. Therefore, mol. tools that discriminate a single base mismatch in the target sequence are required for achieving therapeutic success. Here, we synthesized peptide nucleic acids (PNAs) derivatized with tolane via an amide linkage at the N-terminus and succeeded in improving the sequence specificity, even with a mismatched base pair located near the terminal region of the duplex. We assessed the sequence specificities of the tolane-PNAs for single-strand DNA and RNA by UV-melting temperature anal., thermodn. anal., an in silico conformational search, and a gel mobility shift assay. As a result, all of the PNA-tolane derivatives stabilized duplex formation to the matched target sequence without inducing mismatch target binding. Among the different PNA-tolane derivatives, PNA that was modified with a naphthyl-type tolane could efficiently discriminate a mismatched base pair and be utilized for the detection of resistance to neuraminidase inhibitors of the influenza A/H1N1 virus. Therefore, our mol. tool can be used to discriminate single nucleotide polymorphisms that are related to drug resistance in pathogens.

Molecules 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 C14H28O5S, 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

Takagi, Kenji published the artcileSNP discrimination by tolane-modified peptide nucleic acids: application for the detection of drug resistance in pathogens, Computed Properties of 186046-81-1, the publication is Molecules (2020), 25(4), 769, database is CAplus and MEDLINE.

During the treatment of viral or bacterial infections, it is important to evaluate any resistance to the therapeutic agents used. An amino acid substitution arising from a single base mutation in a particular gene often causes drug resistance in pathogens. Therefore, mol. tools that discriminate a single base mismatch in the target sequence are required for achieving therapeutic success. Here, we synthesized peptide nucleic acids (PNAs) derivatized with tolane via an amide linkage at the N-terminus and succeeded in improving the sequence specificity, even with a mismatched base pair located near the terminal region of the duplex. We assessed the sequence specificities of the tolane-PNAs for single-strand DNA and RNA by UV-melting temperature anal., thermodn. anal., an in silico conformational search, and a gel mobility shift assay. As a result, all of the PNA-tolane derivatives stabilized duplex formation to the matched target sequence without inducing mismatch target binding. Among the different PNA-tolane derivatives, PNA that was modified with a naphthyl-type tolane could efficiently discriminate a mismatched base pair and be utilized for the detection of resistance to neuraminidase inhibitors of the influenza A/H1N1 virus. Therefore, our mol. tool can be used to discriminate single nucleotide polymorphisms that are related to drug resistance in pathogens.

Molecules 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 C19H14Cl2, Computed Properties of 186046-81-1.

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

Duan, Tanghui published the artcileConstruction of tunable peptide nucleic acid junctions, Product Details of C26H26N4O7, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(23), 2846-2849, database is CAplus and MEDLINE.

We report here the construction of 3-way and 4-way peptide nucleic acid (PNA) junctions as basic structural units for PNA nanostructuring. The incorporation of amino acid residues into PNA chains makes PNA nanostructures with more structural complexity and architectural flexibility possible, as exemplified by building 3-way PNA junctions with tunable nanopores. Given that PNA nanostructures have good thermal and enzymic stabilities, they are expected to have broad potential applications in biosensing, drug delivery and bioengineering.

Chemical Communications (Cambridge, United Kingdom) 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

Hudson, Robert H. E. published the artcileOn the Necessity of Nucleobase Protection for 2-Thiouracil for Fmoc-Based Pseudo-Complementary Peptide Nucleic Acid Oligomer Synthesis, Name: 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 (2019), 84(21), 13252-13261, database is CAplus and MEDLINE.

A selection of benzyl-based protecting groups for thiouracil (^SU) for use in in pseudo-complementary peptide nucleic acid (PNA) have been evaluated. The 4-methoxybenzyl protecting group that has found use for ^SU during Boc-based (Boc = tert-butoxycarbonyl) oligomerization is also suitable for Fmoc-based (Fmoc = 9-fluorenylmethoxycarbonyl) oligomerization. Furthermore, it is demonstrated that ^SU protection is unnecessary for the successful synthesis of thiouracil-containing PNA. The rate of acidolysis of the 4-methoxybenzyl protecting group is compared to the recently reported 2-methyl-4-methoxybenzyl group and to the hyper labile the 2,4-dimethoxybenzyl group as well as the surprisingly resistant 2-methoxybenzyl group. The 2-thiothymine (^ST) PNA monomer has also been prepared and incorporated into an oligomer. In the sequence context examined, the ^ST insert resulted in a mild destabilization (ΔTm = -1.0/insert) relative to T, whereas ^SU had a slight stabilizing effect (ΔTm = +0.3/insert).

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, Name: 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

Hudson, Robert H. E. published the artcileOn the Necessity of Nucleobase Protection for 2-Thiouracil for Fmoc-Based Pseudo-Complementary Peptide Nucleic Acid Oligomer Synthesis, 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 Organic Chemistry (2019), 84(21), 13252-13261, database is CAplus and MEDLINE.

A selection of benzyl-based protecting groups for thiouracil (^SU) for use in in pseudo-complementary peptide nucleic acid (PNA) have been evaluated. The 4-methoxybenzyl protecting group that has found use for ^SU during Boc-based (Boc = tert-butoxycarbonyl) oligomerization is also suitable for Fmoc-based (Fmoc = 9-fluorenylmethoxycarbonyl) oligomerization. Furthermore, it is demonstrated that ^SU protection is unnecessary for the successful synthesis of thiouracil-containing PNA. The rate of acidolysis of the 4-methoxybenzyl protecting group is compared to the recently reported 2-methyl-4-methoxybenzyl group and to the hyper labile the 2,4-dimethoxybenzyl group as well as the surprisingly resistant 2-methoxybenzyl group. The 2-thiothymine (^ST) PNA monomer has also been prepared and incorporated into an oligomer. In the sequence context examined, the ^ST insert resulted in a mild destabilization (ΔTm = -1.0/insert) relative to T, whereas ^SU had a slight stabilizing effect (ΔTm = +0.3/insert).

Journal of Organic 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

Gompper, Rudolf published the artcileAminopyridines, aminopyrimidines, and tris(dimethylamino) benzene from (aza) vinamidinium and (aza)pentamethinium salts, Application of N,N-Dimethylpyrimidin-4-amine, the publication is Angewandte Chemie (1981), 93(3), 298-9, database is CAplus.

Reaction of H₂XC(NMe₂):N⁺:CRNMe₂.ClO₄^– (X = CH, R = H, Ph, Me, NMe₂; X = N, R = H) with Me₂NCH(OEt)₂ gave 74-90% Me₂NCH:XC(NMe₂):N⁺:CRNMe₂.ClO₄^– (I). I (X = CH) were cyclized with NH₄OAc to give the pyrimidines II (R = H, Ph, NMe₂). The pyridine III was obtained by treating I (X = CH, R = Me) with base. 1,3,5-(Me₂N)₃C₆H₃ was obtained in 70% yield by treating Me₂NCMe:C:C(NMe₂)₂.HClO₄ with Me₂NCMe(OEt)₂.

Angewandte Chemie 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, Application of N,N-Dimethylpyrimidin-4-amine.

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

Latham, Jonathan published the artcileIntegrated catalysis opens new arylation pathways via regiodivergent enzymatic C-H activation, Recommanded Product: 2-(Dimethylamino)pyrimidine-4,6-diol, the publication is Nature Communications (2016), 11873pp., database is CAplus and MEDLINE.

The integration of regioselective halogenase enzymes with Pd-catalyzed cross-coupling chem., in one-pot reactions, successfully addresses this problem for the indole heterocycle was demonstrated. The resultant ‘chemobio-transformation’ delivered a range of functionally diverse arylated products that were impossible to access using sep. enzymic or chemocatalytic C-H activation, under mild, aqueous conditions. This use of different biocatalysts to select different C-H positions contrasts with the prevailing substrate-control approach to the area, and presented opportunities for new pathways in C-H activation chem. The issues of enzyme and transition metal compatibility were overcome through membrane compartmentalization, with the optimized process requiring no intermediate work-up or purification steps.

Nature Communications 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, Recommanded Product: 2-(Dimethylamino)pyrimidine-4,6-diol.

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

Schleper, A. Lennart published the artcileInfluence of regioisomerism in bis(terpyridine) based exciplexes with delayed fluorescence, Product Details of C4H3Cl2N3, the publication is Journal of Materials Chemistry C: Materials for Optical and Electronic Devices (2022), 10(19), 7699-7706, database is CAplus.

Exciplexes of individual electron donor and acceptor mols. are a promising approach to utilizing otherwise non-emissive triplet states in optoelectronic applications. In this work, we synthesize a series of bis(terpyridine) pyrimidine (BTP) isomers and employ them as electron acceptors in complexes with tris(4-carbazoyl-9-ylphenyl)amine (TCTA). We show that these TCTA : BTP complexes produce thermally activated delayed fluorescence (TADF) by exciplex emission, and we investigate the influence of the nitrogen position in the pyridine on the optical and electronic properties of the exciplex. The mol. arrangement of the complex is studied using scanning tunneling microscopy (STM) as well as classical force field and d. functional theory (DFT) simulations. Finally, we fabricate organic light-emitting diodes (OLEDs) with maximum external quantum efficiencies ranging between 0.5% and 2% – depending on the BTP isomer.

Journal of Materials Chemistry C: Materials for Optical and Electronic Devices 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

Wandlowski, Th. published the artcileStructural and Thermodynamic Aspects of Phase Transitions in Uracil Adlayers. A Chronocoulometric Study, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Langmuir (1996), 12(26), 6604-6615, database is CAplus.

The phase formation of uracil and 5 uracil alkyl derivatives on a Au (111) single crystal electrode from aqueous 0.05 M KClO₄ was studied by using chronocoulometry, cyclic voltammetry, and phase-sensitive ac voltammetry. As a function of the applied electrode potential and/or the adsorbate concentration, uracil (U), 5-methyluracil (5-MU), and 5,6-dimethyluracil (5,6-DMU) exhibit 4 different adsorption regions. These are assigned to a “dilute” phase (I), a 2-dimensional condensed physisorbed film (II), a partial charge transfer/deprotonation region (III), and a chemisorbed film (IV). Substitution of the N (1)- and/or the N (3)-ring N with Me groups prevents the formation of the ordered physisorbed film II. In the case of 1-methyluracil (1-MU) and 3-methyluracil (3-MU), region I is followed immediately by regions III and IV. No indications for the latter 2 regions were found with 1,3-dimethyluracil, where both ring N atoms are blocked simultaneously with Me groups. Quant. thermodn. adsorption parameters (e.g., film pressure, Gibbs surface excess, Gibbs energy of adsorption, and electrosorption valence) were determined on the basis of chronocoulometric measurements for the “dilute” and the 2-dimensional condensed physisorbed film. All of these mols. are oriented parallel to the electrode surface in both ordered regions. The corresponding values of the Gibbs energies of adsorption ΔG_I° and ΔG_II° of the 6 uracil derivatives on Au (111) indicate weak chemisorption. On the basis of structural and energetic data, the formation of the 2D-condensed physisorbed film of U, 5-MU, and 5,6-DMU is interpreted as a replacement of residual interfacial H₂O mols. accompanied by the creation of a 2D network of planar oriented and (via H bonds) interconnected mols. The adsorption and phase formation parameter obtained for the 6 uracil derivatives on Au (111) in regions I and II is complemented by anal. of selected (published) results on Ag (111) and Hg electrodes. No quant. thermodn. data were extracted in regions III and IV.

Langmuir 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 C19H14Cl2, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Brown, D. J. published the artcileSimple pyrimidines. III. Methylation and structure of the aminopyrimidines, Application of N,N-Dimethylpyrimidin-4-amine, the publication is Journal of the Chemical Society (1955), 4035-40, database is CAplus.

cf. C.A. 49, 14000f. 2- (I) and 4-aminopyrimidine (II) were shown to exist largely in the amino form, by comparison of their basic strength, and ultraviolet and infrared spectra with those of the corresponding nuclear and extranuclear N-Me derivatives The preparation of the nuclear N-Me derivatives involved the methylation of I and II to 1,2-dihydro-2- (III) and 1,4-dihydro-4-imino-1-methylpyrimidine (IV), resp. In alk. solution, III rearranged to 2-methylaminopyrimidine (V), while IV was hydrolyzed to 1,4-dihydro-1-methyl-4-oxopyrimidine (VI). The ultraviolet spectra of the cations of I and II were similar to those of the cations of III and IV, which suggested that a proton was bonded to a nuclear N atom in cations from I and II. This view was suggested by the marked difference between the spectra of the cations of I, II, V, 2-dimethylamino (VII), 4-methylamino- (VIII), and 4-dimethylaminopyrimidine (IX) and that of the neutral mol. of pyrimidine itself. For the neutral molecules of I and II the ultraviolet absorption curves were quantitatively displaced along the wavelength scale from those of the corresponding nuclear N-Me derivatives (III and IV) than from those of the extranuclear N-Me analogs V, VII, VIII, and IX. There is the possibility of some amine-imine tautomerism. The extent of such tautomerism was calculated from the ionization constants of the N-Me series fixed in the amino and imino forms. K_tautometric = [amine]/(imine] = K_a[amino]/K_a[imino]. By using the ionization constants of III, IV, V, VII, VIII, and IX it was found that the amine-imine tautomeric constant in aqueous solution was of the order of 10⁶ for both I and II. In the solid state and in nonaqueous solvents I and II similarly exist largely in the amino form as was shown by their infrared spectra. Both I and II in CCl₄ gave 2 sharp bands at 3540 and 3430 cm.^-1 due to asym. and sym. stretching modes of the unassocd. NH₂ group and 2 broad bands at 3320 and 3170 cm.^-1 due to vibration modes of the intermol. H-bonded NH₂ group. V and VIII give only 1 sharp band at 3460 cm.^-1 and a broad one near 3260 cm.^-1 In the double-bond stretching region, I and II showed a strong band at 1650 cm.^-1 which was due to internal deformation of the NH₂ group, for it disappeared upon deuteriation. In the same region the salts of III and IV absorbed strongly at 1646 cm.^-1 and the deuteriated compounds showed some absorption, which may be due to the C:N stretching mode. V and VIII showed a strong band near 1615 cm.^-1 and were unaffected by deuteriation. I (5 g.), 10 ml. MeI, and 60 ml. MeOH were kept 5 days at room temperature to give 2.9 g. III hydriodide (X), m. 247-8° (decomposition) (from 95% EtOH). X (0.23 g.) cooled to 0°, moistened with H₂O, covered with Et₂O, and then ground with 1 g. powd. KOH and the Et₂O solution separated, dried, and concentrated yielded crude III. Recrystallization of III was carried out by solution in Et₂O, drying, filtering through cotton, concentrating, cooling to room temperature, filtering with a filter stick, and drying in a desiccator over CaCl₂ to yield pure III, yellow needles, m. 102-4°; picrate, m. 198-200° (from EtOH). X (1 g.) heated 10 min. in 12 ml. NaOH solution yielded 71% V, m. 59-60°; picrate, m. 191° (mixed m.p. with III picrate showed a depression). II (5 g.), 5 ml. MeI, and 25 ml. MeOH refluxed 1 hr. gave 10 g. IV hydriodide (XI), m. 205-6° (from EtOH). In another experiment the reactants were left 3 days at room temperature to give XI, m. 163-4°. Recrystallization of this lower-melting form or storage for 3 days gave the higher-melting form. XI picrate, m. 172-3° (from EtOH). XI (0.9 g.) left 10 hrs. at 20-5° with 0.1N NaOH, HCl added to pH 5, the solution evaporated and the residue treated with picric acid yielded 55% VI picrate, m. 164-6°. VI picrate, prepared from authentic base also m. 164-6°. The 2 specimens showed no mixed m.p. depression. An attempt to prepare 1,2,3,4-tetrahydro-2,4-diimino-1,3-dimethylpyrimidine gave only a single monomethylated derivative of indeterminate structure.

Journal of the Chemical Society 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, Application of N,N-Dimethylpyrimidin-4-amine.

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