Category: pyrimidines

Fox, Jack F. published the artcilePyrimidine nucleosides. XII. Direct synthesis of 2′-deoxycytidine and its α-anomer, Application of 4-(1H-1,2,3,4-Tetrazol-5-yl)pyrimidine, the publication is Journal of the American Chemical Society (1961), 4066-50, database is CAplus.

The direct synthesis of 2′-deoxycytidine (I) was achieved via the mercuri method involving the condensation of 3,5 di-O-(p-chlorobenzoyl)-2-deoxy-D-ribosyl chloride (II) with mercuri-N-acetylcytosine (III). The α-anomer (IV) of I was also obtained from this reaction. The synthesis of II from 2-deoxy-D-ribose (V) was described. The optical rotations of I and IV, as well as those of their acylated intermediates, did not conform to Hudson’s rules of isorotation. The synthesis of other fully acylated derivatives of 2-deoxy-D-ribofuranose from preformed purine-2-deoxy-D-ribonucleosides also was described. V (20.0 g.) in 380 cc. absolute MeOH treated 20 min. at 27° with 20 cc. 1% HClMeOH, stirred with 10.0 g. Ag₂CO₃, filtered and evaporated, the residue dissolved in C₅H₅N, concentrated, and dissolved in 115 cc. dry C₅H₅N, the solution treated 16 hrs. with cooling with 45 cc. p-ClC₆H₄COCl and diluted with H₂O and CH₂Cl₂, the organic layer worked up, and the sirupy Me 3,5-di-O-(p-chlorobenzoyl)-2-deoxy-D-ribofuranoside dissolved in 150 cc. dry Et₂O, cooled to 0°, treated with 200 cc. cold AcOH (saturated with dry HCl), saturated below 10° with dry HCl, and filtered gave 28.0 g. II, m. 118-20° (decomposition). II (0.005 mole) added with stirring to 0.0025 mole dry III in 40 cc. refluxing xylene, cooled, filtered, and diluted with 300 cc. petr. ether and the precipitate purified gave 0.8 g. 1-[3,5-di-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribosyl]-4-acetamido-2(1H)-pyrimidinone (VI) and β-anomer; the mother liquor gave 0.1 g. unidentified, N-free, crystalline material, m. about 160°. α-and β-VI mixture (0.8 g.) in about 20 cc. hot EtOH when cooled deposited about 0.3 g. α-VI, needles, m. 200-1° with sintering at about 160°, resolidifying, and remelting with effervescence at about 230°; this material recrystallized from about 25 cc. boiling EtOH gave short needles, m. 204.5-205°, becoming turbid at 208°, resolidifying at 210°, and remelting with decomposition at about 245°, [α]²⁵_D -66° (c 0.9, CHCl₃); the mother liquor from the α-VI concentrated to 10 cc. and cooled gave 0.44 g. β-VI, m. 128-30° (hot EtOH), resolidifying and remelting with decomposition and effervescence at about 240°, [α]²⁵_D -19° (c 0.9, CHCl₃). α-VI (250 mg.) in 30 cc. absolute EtOH (saturated at 0° with dry NH₃) heated 12 hrs. at 100° in a sealed tube and worked up gave 100 mg. IV, m. 192-3° (EtOH), [α]²⁵_D -44° (c 0.7, N NaOH); picrate, microscopic prisms, m. 173-5° (decomposition and effervescence) (95% EtOH). β-VI (300 mg.) gave similarly I, m. 199-200° (MeOH and Et₂O); picrate, yellow needles, m. 192-8°. Deoxyadenosine (20.1 g.) dissolved with stirring in about 750 cc. dry C₅H₅N, cooled, treated with stirring dropwise with 28 cc. BzCl, kept 48 hrs. at 37-9°, concentrated in vacuo to about 200 cc., and stirred into about 200 cc. ice and H₂O, and the aqueous layer decanted gave 37 g. glassy solid; the product heated 2 hrs. with stirring on the steam bath with 1700 cc. 2N H₂SO₄ and 500 cc. Bu₂O, the aqueous layer again refluxed 1 hr. with 500 cc. Bu₂O, and the combined organic phases cooled, filtered, and worked up gave 19 g. 3,5-di-O-benzoyl-D-ribose (VII). 2′-Deoxyguanosine benzoylated in a similar manner and the product dissolved in dioxane and refluxed with Bu₂O and 2N H₂SO₄ gave 65% VII. VII (0.056 mole) in 60 cc. dry C₅H₅N and 80 cc. CH₂Cl₂ treated 2 days at room temperature with 17.1 g. Ac₂O, evaporated below 50° in vacuo, poured into iced H₂O, and extracted with CHCl₃, and the extract worked up yielded 22% (crude) 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-D-ribose, m. 86.5-7.5° (EtOH), [α]²⁶_D -23° (c 2.0, CHCl₃). VII benzoylated in a similar manner gave 15% 1,3,5-tri-O-benzoyl-2-deoxy-D-ribose, needles, m. 110-11° (EtOH), [α]²⁵_D 75° (c 2.54, CHCl₃); the original mother liquor yielded 7% of an isomer, needles, m. 83-6° (EtOH), [α]²⁵_D -20° (c 1.1, CHCl₃). The infrared absorption spectra of I and IV were recorded.

Journal of the American Chemical Society published new progress about 92306-69-9. 92306-69-9 belongs to pyrimidines, auxiliary class Tetrazoles, name is 4-(1H-1,2,3,4-Tetrazol-5-yl)pyrimidine, and the molecular formula is C5H4N6, Application of 4-(1H-1,2,3,4-Tetrazol-5-yl)pyrimidine.

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

Schreeb, A. published the artcilePiperazine modification in 2,4,6-triaminopyrimidine derivatives as histamine H4 receptor ligands, Safety of 2-Amino-4,6-dichloropyrimidine, the publication is Pharmazie (2013), 68(7), 521-525, database is CAplus and MEDLINE.

The human histamine H₄ receptor (hH₄R) is a promising new target in the therapy of inflammatory and immunomodulatory diseases. The 2,4,6-triaminopyrimidine structure has been established as a potent hH₄R affinity scaffold. By using the inverse agonist ST-1012 as reference ligand, piperazine modifications were performed to get larger structural variations. Therefore, different spacers were introduced into the lead structure and the influence on affinity of this basic element was evaluated. While a short distance between aminopyrimidine and basic moiety is beneficial, a lipophilic group in the eastern part is necessary to maintain hH₄R affinity. The title compounds thus formed included a piperazine pyrimidine indoline derivative (I) and related substances, such as 4,6-bis(4-methyl-1-piperazinyl)-2-pyrimidinamine. The synthesis of the target compounds was achieved by a reaction of 4,6-dichloro-2-pyrimidinamine with 4-methyl-1-piperazineethanamine, 4-methyl-1-piperazinepropanamine, 4-methyl-1-piperazinebutanamine, etc.

Pharmazie 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

Herbich, Jerzy published the artcileExcited charge transfer states in 4-aminopyrimidines, 4-(dimethylanilino)pyrimidine and 4-(dimethylamino)pyridine, Category: pyrimidines, the publication is Chemical Physics (1994), 188(2,3), 247-65, database is CAplus.

This paper presents a comparative study of the photoinduced electron transfer in a series of donor-acceptor compounds and their hydrogen-bonded complexes in solution 4-(Dimethylamino)pyridine (III), similarly to 4-(dimethylamino)pyrimidine (I) and 4-(dimethylamino)-5-methylpyrimidine (II) and contrary to 4-(N,N-dimethylanilino)pyrimidine (IV), shows dual luminescence in a sufficiently polar and mobile environment. The results of steady-state and kinetic investigations as well as quantum chem. calculations of I–III fit well into the twisted intramol. charge transfer (TICT) state model. On the other hand, the results suggest an enhanced planarity of the ICT fluorescent state of IV. INDO/S calculations confirm the large probability of the allowed radiative transitions in the latter compound Photophysics of all the compounds under study is modified by hydrogen bonding: fluorescence quantum yields are strongly reduced in the presence of alcs.

Chemical Physics 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, Category: pyrimidines.

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

Sanders, Jeffrey M. published the artcileEffects of Hypoxanthine Substitution in Peptide Nucleic Acids Targeting KRAS2 Oncogenic mRNA Molecules: Theory and Experiment, SDS of cas: 169396-92-3, the publication is Journal of Physical Chemistry B (2013), 117(39), 11584-11595, database is CAplus and MEDLINE.

Genetic disorders can arise from single base substitutions in a single gene. A single base substitution for wild type guanine in the twelfth codon of KRAS2 mRNA occurs frequently to initiate lung, pancreatic, and colon cancer. We have observed single base mismatch specificity in radioimaging of mutant KRAS2 mRNA in tumors in mice by in vivo hybridization with radiolabeled peptide nucleic acid (PNA) dodecamers. We hypothesized that multimutant specificity could be achieved with a PNA dodecamer incorporating hypoxanthine, which can form Watson-Crick base pairs with adenine, cytosine, thymine, and uracil. Using mol. dynamics simulations and free energy calculations, we show that hypoxanthine substitutions in PNAs are tolerated in KRAS2 RNA:PNA duplexes where wild type guanine is replaced by mutant uracil or adenine in RNA. To validate our predictions, we synthesized PNA dodecamers with hypoxanthine, and then measured the thermal stability of RNA:PNA duplexes. CD thermal melting results showed that hypoxanthine-containing PNAs are more stable in duplexes where hypoxanthine-adenine and hypoxanthine-uracil base pairs are formed than single mismatch duplexes or duplexes containing hypoxanthine-guanine opposition.

Journal of Physical Chemistry B 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, SDS of cas: 169396-92-3.

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

Sanders, Jeffrey M. published the artcileEffects of Hypoxanthine Substitution in Peptide Nucleic Acids Targeting KRAS2 Oncogenic mRNA Molecules: Theory and Experiment, Formula: C39H35N5O8, the publication is Journal of Physical Chemistry B (2013), 117(39), 11584-11595, database is CAplus and MEDLINE.

Genetic disorders can arise from single base substitutions in a single gene. A single base substitution for wild type guanine in the twelfth codon of KRAS2 mRNA occurs frequently to initiate lung, pancreatic, and colon cancer. We have observed single base mismatch specificity in radioimaging of mutant KRAS2 mRNA in tumors in mice by in vivo hybridization with radiolabeled peptide nucleic acid (PNA) dodecamers. We hypothesized that multimutant specificity could be achieved with a PNA dodecamer incorporating hypoxanthine, which can form Watson-Crick base pairs with adenine, cytosine, thymine, and uracil. Using mol. dynamics simulations and free energy calculations, we show that hypoxanthine substitutions in PNAs are tolerated in KRAS2 RNA:PNA duplexes where wild type guanine is replaced by mutant uracil or adenine in RNA. To validate our predictions, we synthesized PNA dodecamers with hypoxanthine, and then measured the thermal stability of RNA:PNA duplexes. CD thermal melting results showed that hypoxanthine-containing PNAs are more stable in duplexes where hypoxanthine-adenine and hypoxanthine-uracil base pairs are formed than single mismatch duplexes or duplexes containing hypoxanthine-guanine opposition.

Journal of Physical Chemistry B 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

Xu, Jianjun published the artcileSynthesis and properties of a high-performance pyrimidine-containing self-catalyzed phthalonitrile polymer, Synthetic Route of 56-05-3, the publication is Journal of Polymer Science, Part A: Polymer Chemistry (2019), 57(23), 2287-2294, database is CAplus.

A self-catalytic monomer of phthalonitrile, 2-amino-4,6-bis[3-(3,4-dicyano-phenoxy)phenoxy] pyrimidine (ACPP), was synthesized by a one-pot method with resorcinol, 2-amino-4,6-dichloropyrimidine, and 4-nitrophthalonitrile. The chem. structure of the ACPP monomer was characterized by Fourier transform IR spectroscopy and NMR spectroscopy. The curing behavior of ACPP monomer was studied by differential scanning calorimetric, which indicated that the ACPP monomer had a low m.p. (84 °C) and revealed an autocatalytic reaction and tremendously wide processing window (193 °C). Wide-angle X-ray diffraction and FTIR analyzes were employed to explore the microstructure of the ACPP polymers. The properties of the three polymers with different curing procedures were investigated, which implied that the ACPP polymers exhibited excellent thermal stability, high modulus, superior glass-transition temperature (T_g > 400 °C), and low water absorption with the increase in curing extent.

Journal of Polymer Science, Part A: Polymer 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 C18H34N4O5S, Synthetic Route of 56-05-3.

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

Leng, Jiapeng published the artcileIntegration of high accuracy N-terminus identification in peptide sequencing and comparative protein analysis via isothiocyanate-based isotope labeling reagent with ESI ion-trap TOF MS, Product Details of C4H3Cl2N3, the publication is Journal of the American Society for Mass Spectrometry (2011), 22(7), 1204-1213, database is CAplus and MEDLINE.

A multifunctional isothiocyanate-based isotope labeling reagent, [d₀]-/[d₆]-4,6-dimethoxy pyrimidine-2-isothiocyanate (DMPITC), has been developed for accurate N-terminus identification in peptide sequencing and comparative protein anal. by ESI Ion-trap TOF mass spectrometry. In contrast with the conventional labeling reagent Ph isothiocyanate (PITC), DMPITC showed more desirable properties such as rapid labeling, sensitivity enhancement, and facilitating peptide sequencing. More significantly, DMPITC-based labeling strategy possessed the capacity of higher reliable N-terminus identification owning to the high-yield b₁ ion combined with the isotope validation of 6 Da. Meanwhile, it also showed potential in differentiating isomeric residues of leucine and isoleucine at N-terminus on the basis of the relative abundance ratios between the fragment ions of their resp. b₁ ions. The strategy not only allows accurate interpretation for peptide but also ensures rapid and sensitive comparative anal. for protein by direct MS anal. Using trypsin-digested bovine serum albumin (BSA), both peptide N-terminus identification and quant. anal. were accomplished with high accuracy, efficiency, and reproducibility. The application of DMPITC-based labeling strategy is expected to serve as a promising tool for proteome research.

Journal of the American Society for Mass Spectrometry 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

Li, Jia-hui published the artcileSynthesis, herbicidal activity study and molecular docking of novel pyrimidine thiourea, HPLC of Formula: 56-05-3, the publication is Pesticide Biochemistry and Physiology (2021), 104766, database is CAplus and MEDLINE.

According to the pharmacophore binding strategy and principle of bioelectronic isobaric, used the sulfonylurea bridge as the parent structure, a series of novel thiourea compounds containing aromatic-substituted pyrimidines I (R¹ = OMe, Cl, N(Et)₂, etc.; R² = Me, OEt, Cl, etc.) were designed and synthesized. The preliminary herbicidal activity tests showed that some compounds had good herbicidal activity against Digitaria adscendens, Amaranthus retroflexus, especially for compound I (R¹ = OMe; R² = Cl) and compound I (R¹ = R² = Cl). The results showed that compound I (R¹ = OMe; R² = Cl) had an inhibition rate of 81.5% on the root growth of Brassica napus L. at the concentration of 100 mg L^-1, and compound I (R¹ = R² = Cl) had an inhibition rate of 81% on the root growth of Digitaria adscendens at the concentration of 100 mg L^-1. Compounds I (R¹ = OMe; R² = Cl) and I (R¹ = R² = Cl) had higher comparative activity on Echinochloa crus-galli than the com. herbicide bensulfuron-Me. The preliminary structure-activity relationship (SAR) was also summarized. Authors also tested the in vivo AHAS enzyme activity inhibition experiment of 14 compounds at 100 mg L^-1, and the results showed that they all have inhibitory activity on the enzyme, with the highest inhibition rate reaching 44.4% (compound I (R¹ = OMe; R² = Cl)). Based on the results of mol. docking to yeast acetohydroxyacid synthase (AHAS), the possible herbicidal activity mechanism of these compounds was evaluated.

Pesticide Biochemistry and Physiology 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

Cowden, William B. published the artcileCan nitrogen-15 NMR be used to determine the site of N-oxidation of pyrimidine-2,4-diamine?, Related Products of pyrimidines, the publication is Australian Journal of Chemistry (1981), 34(7), 1539-43, database is CAplus.

An examination of the products of N-oxidation of pyrimidine-2,4-diamine demonstrated that ¹⁵N spectroscopy is an unreliable technique for the determination of the site of N-oxidation The ¹⁵N shifts caused by N-oxidation were small and downfield and of no diagnostic value.

Australian Journal of Chemistry published new progress about 74638-76-9. 74638-76-9 belongs to pyrimidines, auxiliary class Pyrimidine, name is 2,4-Diaminopyrimidine-3-oxide, and the molecular formula is C4H6N4O, Related Products of pyrimidines.

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

Zhang, Xiao published the artcileStructural insights into FTO’s catalytic mechanism for the demethylation of multiple RNA substrates, Application In Synthesis of 608-34-4, the publication is Proceedings of the National Academy of Sciences of the United States of America (2019), 116(8), 2919-2924, database is CAplus and MEDLINE.

FTO demethylates internal N6-methyladenosine (m6A) and N6,2′-O-dimethyladenosine (m6Am; at the cap +1 position) in mRNA, m6A and m6Am in snRNA, and N1-methyladenosine (m1A) in tRNA in vivo, and in vitro evidence supports that it can also demethylate N6-methyldeoxyadenosine (6mA), 3-methylthymine (3mT), and 3-methyluracil (m3U). However, it remains unclear how FTO variously recognizes and catalyzes these diverse substrates. Here we demonstrate – in vitro and in vivo – that FTO has extensive demethylation enzymic activity on both internal m6A and cap m6Am. Considering that 6mA, m6A, and m6Am all share the same nucleobase, we present a crystal structure of human FTO bound to 6mA-modified ssDNA, revealing the mol. basis of the catalytic demethylation of FTO toward multiple RNA substrates. We discovered that (i) N6-methyladenine is the most favorable nucleobase substrate of FTO, (ii) FTO displays the same demethylation activity toward internal m6A and m6Am in the same RNA sequence, suggesting that the substrate specificity of FTO primarily results from the interaction of residues in the catalytic pocket with the nucleobase (rather than the ribose ring), and (iii) the sequence and the tertiary structure of RNA can affect the catalytic activity of FTO. Our findings provide a structural basis for understanding the catalytic mechanism through which FTO demethylates its multiple substrates and pave the way forward for the structure-guided design of selective chems. for functional studies and potential therapeutic applications.

Proceedings of the National Academy of Sciences of the United States of America 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 C10H10O3, Application In Synthesis of 608-34-4.

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