Day: December 6, 2022

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

Tsuno, Naoki published the artcilePharmacological evaluation of novel (6-aminopyridin-3-yl)(4-(pyridin-2-yl)piperazin-1-yl) methanone derivatives as TRPV4 antagonists for the treatment of pain, COA of Formula: C5H5ClN2O2S, the publication is Bioorganic & Medicinal Chemistry (2017), 25(7), 2177-2190, database is CAplus and MEDLINE.

A novel series of (6-aminopyridin-3-yl)(4-(pyridin-2-yl)piperazin-1-yl) methanone derivatives were identified as selective transient receptor potential vanilloid 4 (TRPV4) channel antagonist and showed analgesic effect in Freund’s Complete Adjuvant (FCA) induced mech. hyperalgesia model in guinea pig and rat. Modification of right part based on the compound I which was disclosed in the previous communication led to the identification of compound II as a flagship compound In this paper, the authors described the details about design, synthesis and structure-activity relationship (SAR) anal.

Bioorganic & Medicinal Chemistry published new progress about 321565-33-7. 321565-33-7 belongs to pyrimidines, auxiliary class Pyrimidine, name is 2-Chloro-5-methanesulfonylpyrimidine, and the molecular formula is C5H6N2O2, COA of Formula: C5H5ClN2O2S.

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

Xu, Liang published the artcileSynthesis and Biological Activities of O,O-Dialkyl 1-((4,6-Dichloropyrimidin-2-yl)Carbamyloxy) Alkylphosphonates, Computed Properties of 56-05-3, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (2014), 189(6), 812-818, database is CAplus.

A series of new 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy) alkylphosphonates were designed and synthesized. The structures of all the title compounds were confirmed by IR, ¹H-NMR, ³¹P-NMR and elemental anal. The results of the bioassay showed that all of title compounds exhibited weak herbicidal activities against monocotyledons and dicotyledons; however, some of them showed potential plant growth regulatory activities.

Phosphorus, Sulfur and Silicon and the Related Elements 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 C8H8BFO2, Computed Properties of 56-05-3.

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

Itahara, Toshio published the artcileSelf-organization of adenine and thymine derivatives in thermotropic liquid crystal, Formula: C5H6N2O2, the publication is Journal of Molecular Structure (2007), 827(1-3), 95-100, database is CAplus.

Self-organization of adenine and thymine derivatives was studied by comparison of IR spectra of these compounds in crystal, liquid crystal, and isotropic liquid states. The adenine derivative mainly formed weaker hydrogen-bonded assemblies in the liquid crystal state, compared with assemblies in crystal state. The thymine derivative existed as a component of a network of prolonged hydrogen bonds interconnecting thymine rings in the liquid crystal state. The mixing of the adenine and thymine derivatives at a molar ratio of 1:1 resulted in a formation of base pair between adenine and thymine rings. The structures of hydrogen-bonded assemblies in the liquid crystal state were presumed on the basis of the temperature-dependent IR spectra.

Journal of Molecular Structure 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

Alpturk, Onur published the artcileOptimization of synthetic route to PNA-T-OH monomers, 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 the Turkish Chemical Society, Section A: Chemistry (2018), 5(2), 457-468, database is CAplus.

Peptide nucleic acids are synthetic mols. crafted to mimic natural nucleic acids, and thus, they are widely utilized in many chem., and, biomedical applications. Although there exist many approaches to synthesize monomers to date, there is still room to improve these methodologies. With this motivation, we compared some widely utilized synthetic routes to obtain N-Boc-PNA-T-OH, and N-Fmoc-PNA-T-OH (Fmoc = 9-fluorenyl-methoxycarbonyl). Our results indicate that N-Boc-ethylenediamine (Boc =tert-butoxycarbonyl) is the most pivotal intermediate in the chem. of PNA, and synthetic route commencing with this material affords these two PNA monomers in relatively high yield, and purity, while being very reproducible.

Journal of the Turkish Chemical Society, Section A: 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

Shemesh, Yossi published the artcilePNA-Rose Bengal Conjugates as Efficient DNA Photomodulators, Application In Synthesis of 186046-81-1, the publication is Bioconjugate Chemistry (2015), 26(9), 1916-1922, database is CAplus and MEDLINE.

Selective photoinduced modulation of DNA may provide a powerful therapeutic tool allowing spatial and temporal control of the photochem. reaction. We have explored the photoreactivity of peptide nucleic acid (PNA) conjugates that were conjugated to a highly potent photosensitizer, Rose Bengal (RB). In addition, a short PEGylated peptide (K-PEG₈-K) was conjugated to the C-terminus of the PNA to improve its water solubility A short irradiation (visible light) of PNA conjugates with a synthetic DNA resulted in highly efficient photomodulation of the DNA as evidenced by polyacrylamide gel electrophoresis (PAGE). In addition, a PNA-RB conjugate replacing K-PEG₈-K with four L-glutamic acids (E₄) was found to be photoinactive. Irradiation of active PNA-RB conjugates with synthetic DNA in D₂0 augments the photoactivity; supporting the involvement of singlet oxygen. PAGE, HPLC, and MALDI-TOF analyses indicate that PNA-DNA photo-crosslinking is a significant pathway in the observed photoreactivity. Selective photo-crosslinking of such PNA-RB conjugates may be a novel approach to selective photodynamic therapy (sPDT) as such mols. would be sequence-specific, cell-permeable, and photoactivated in the visible region.

Bioconjugate 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 C15H16O3, Application In Synthesis of 186046-81-1.

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

Shemesh, Yossi published the artcilePNA-Rose Bengal Conjugates as Efficient DNA Photomodulators, HPLC of Formula: 169396-92-3, the publication is Bioconjugate Chemistry (2015), 26(9), 1916-1922, database is CAplus and MEDLINE.

Selective photoinduced modulation of DNA may provide a powerful therapeutic tool allowing spatial and temporal control of the photochem. reaction. We have explored the photoreactivity of peptide nucleic acid (PNA) conjugates that were conjugated to a highly potent photosensitizer, Rose Bengal (RB). In addition, a short PEGylated peptide (K-PEG₈-K) was conjugated to the C-terminus of the PNA to improve its water solubility A short irradiation (visible light) of PNA conjugates with a synthetic DNA resulted in highly efficient photomodulation of the DNA as evidenced by polyacrylamide gel electrophoresis (PAGE). In addition, a PNA-RB conjugate replacing K-PEG₈-K with four L-glutamic acids (E₄) was found to be photoinactive. Irradiation of active PNA-RB conjugates with synthetic DNA in D₂0 augments the photoactivity; supporting the involvement of singlet oxygen. PAGE, HPLC, and MALDI-TOF analyses indicate that PNA-DNA photo-crosslinking is a significant pathway in the observed photoreactivity. Selective photo-crosslinking of such PNA-RB conjugates may be a novel approach to selective photodynamic therapy (sPDT) as such mols. would be sequence-specific, cell-permeable, and photoactivated in the visible region.

Bioconjugate 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 C16H18O4, HPLC of Formula: 169396-92-3.

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

Jumaa, Mustafa N. published the artcileStudy of genetic variations of FTO gene and its relationship to obese in Iraqi population, Synthetic Route of 608-34-4, the publication is Pharma Chemica (2016), 8(18), 242-254, database is CAplus.

This study included 120 of obese males with mean age 20-50 yr and 50 aged-matched healthy males as a control. The obese patients classified into 3 groups based on Body Mass Index (BMI). DNA was isolated from the collected blood samples and applied for PCR using primers designed for exons 3 and 9 of FTO gene. The results showed that there are 8 mutations in the exon 3. Seven of the mutations are transition and one is transversion. Furthermore, seven of which are predicted to be missense and one is silent. As for exon 9, twelve mutations were identified. Eight of the mutations are transversion and 4 are transition, whereas eleven of which are predicted to be missense and one is silent. The mutations in both 3 and 9 exons recorded a significant differences (p ≤ 0.05) with a Chi-square (X2) 63.229 and 24.802 resp. in the incidence of the pathogenicity comparison to the control.

Pharma Chemica 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, Synthetic Route of 608-34-4.

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

Karim, Rezaul Md published the artcileDiscovery of Dual TAF1-ATR Inhibitors and Ligand-Induced Structural Changes of the TAF1 Tandem Bromodomain, Application In Synthesis of 56-05-3, the publication is Journal of Medicinal Chemistry (2022), 65(5), 4182-4200, database is CAplus and MEDLINE.

Bromodomains regulate chromatin remodeling and gene transcription through recognition of acetylated lysines on histones and other proteins. Bromodomain-containing protein TAF1, a subunit of general transcription factor TFIID, initiates preinitiation complex formation and cellular transcription. TAF1 serves as a cofactor for certain oncogenic transcription factors and is implicated in regulating the p53 tumor suppressor. Therefore, TAF1 is a potential target to develop small mol. therapeutics for diseases arising from dysregulated transcription, such as cancer. Here, we report the ATR kinase inhibitor AZD6738 (Ceralasertib) and analogs thereof as bona fide inhibitors of TAF1. Crystallog. and small-angle X-ray scattering studies established that newly identified and previously reported inhibitors stabilize distinct structural states of the TAF1 tandem bromodomain through “open-closed” transitions and dimerization. Combined with functional studies on p53 signaling in cancer cell lines, the data provide new insights into the feasibility and challenges of TAF1 inhibitors as chem. probes and therapeutics.

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, Application In Synthesis of 56-05-3.

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

Manzoor, Saira published the artcileTetrazole and Azido Derivatives of Pyrimidine: Synthesis, Mechanism, Thermal Behaviour & Steering of Azido-Tetrazole Equilibrium, Product Details of C4H3Cl2N3, the publication is ChemistrySelect (2020), 5(18), 5414-5421, database is CAplus.

A new family of pyrimidine modified tetrazole & azido derivatives I (R = pyrimidin-2-yl, 2,6-dimethoxypyrimidin-4-yl, 6-azidopyrimidin-4-yl, etc.), II, III, IV and tetrazolo[1,5-c]pyrimidin-5-amine was developed using the conventional and nucleophilic substitution methods. The 1H-(tetrazol-1-yl)pyrimidine I compounds were prepared via traditional cycloaddition and condensation method. The compounds tetrazolo[1,5-a]pyrimidine (II, III and IV), azido-(1H-tetrazol-1-yl)pyrimidine I (R = 6-azidopyrimidin-4-yl and 4-azido-6-chloropyrimidin-2-yl) and tetrazolo[1,5-c]pyrimidin-5-amine were synthesized by simultaneously introducing conventional and nucleophilic substitution approaches. The latter technique was easy to process and reduce the synthesis time. The factors (solvent, temperature, steric effect, electron-donating groups, and electron-withdrawing groups) were found responsible for steering the azido-tetrazole equilibrium in the compounds II, III, IV and tetrazolo[1,5-c]pyrimidin-5-amine. All the prepared compounds were well characterized including single-crystal X-ray diffraction structures of some compounds Thermal behavior was investigated by differential scanning calorimetry (DSC) and thermal gravimetric anal. (TGA). The current work is significant to the development of a new class of pyrimidine modified tetrazole and azido derivatives in sense of easy reaction approach, good to excellent yields, safe process, and simple work-ups.

ChemistrySelect 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