Tag: M.W=100-150

Jia, Guifang published the artcileOxidative demethylation of 3-methylthymine and 3-methyluracil in single-stranded DNA and RNA by mouse and human FTO, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is FEBS Letters (2008), 582(23+24), 3313-3319, database is CAplus and MEDLINE.

The human obesity susceptibility gene, FTO, encodes a protein that is homologous to the DNA repair AlkB protein. The AlkB family proteins utilize iron(II), α-ketoglutarate (α-KG) and dioxygen to perform oxidative repair of alkylated nucleobases in DNA and RNA. We demonstrate here the oxidative demethylation of 3-methylthymine (3-meT) in single-stranded DNA (ssDNA) and 3-methyluracil (3-meU) in single-stranded RNA (ssRNA) by recombinant human FTO protein in vitro. Both human and mouse FTO proteins preferentially repair 3-meT in ssDNA over other base lesions tested. They showed negligible activities against 3-meT in double-stranded DNA (dsDNA). In addition, these two proteins can catalyze the demethylation of 3-meU in ssRNA with a slightly higher efficiency over that of 3-meT in ssDNA, suggesting that methylated RNAs are the preferred substrates for FTO.

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

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

Shkurko, O. P. published the artcileEquilibrium NH-acidity of substituted aminopyrimidines, SDS of cas: 56621-93-3, the publication is Zhurnal Organicheskoi Khimii (1981), 17(2), 312-17, database is CAplus.

The transmetalation method was used to determine the NH acidity (pK) of thirty-nine 2-, 4-, and 5-aminopyrimidines; the pK values ranged from 17.7 for 5-nitro-2-pyrimidinamine to 30.2 for 2-(dimethylamino)-5-pyrimidinamine. Comparison with the pK of aniline showed that the ring N atoms had an acidifying effect in the order 4-aza ≫ 2-aza > 3-aza. LFER of the pK vs. NMR chem. shifts, and inductive or resonance substituent constants were described.

Zhurnal Organicheskoi Khimii 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 C17H37NO3, SDS of cas: 56621-93-3.

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

Cohen, Sasson published the artcileThe preparation and properties of 6-halomethylpurines, Recommanded Product: N,N-Dimethylpyrimidin-4-amine, the publication is Journal of Organic Chemistry (1962), 3545-9, database is CAplus.

6-Methylpurine (I) was converted by sulfuryl chloride or N-chlorosuccinimide into 6-trichloromethylpurine in trifluoroacetic acid solution. Stepwise or partial chlorination of the methyl group was not achieved. N-Bromosuccinimide converted I into the 6-dibromo- and, by further substitution, 6-tribromomethylpurine. Stepwise catalytic reduction of the trihalomethylpurines afforded dihalo- and monohalomethylpurines. The chem. and phys. properties of the new compounds are described.

Journal of Organic Chemistry 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, Recommanded Product: N,N-Dimethylpyrimidin-4-amine.

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

Gambacorta, Augusto published the artcileHSAB-driven chemoselective N¹-alkylation of pyrimidine bases and their 4-methoxy- or 4-acetylamino-derivatives, HPLC of Formula: 608-34-4, the publication is Tetrahedron (2006), 62(29), 6848-6854, database is CAplus.

The lithium salts of the conjugated bases of 4-methoxy- and 4-acetylamino-2(1H)-pyrimidinone derivatives undergo highly chemoselective N¹-methylation or ethylation when treated with Me sulfate or Et sulfate (hard electrophiles) in dry dioxane, while the use of DMF as solvent results in competitive O²-alkylation. Potassium salts of the same bases in DMF undergo prevalent O²-attack. Under the same conditions, a similar but less chemoselective behavior is observed in alkylation of thymine and uracil, where some N³-attack occurs. This can be rationalized in terms of the HSAB principle.

Tetrahedron 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, HPLC of Formula: 608-34-4.

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

Hoang, Van-Hai published the artcileDiscovery of Potent Human Glutaminyl Cyclase Inhibitors as Anti-Alzheimer’s Agents Based on Rational Design, Related Products of pyrimidines, the publication is Journal of Medicinal Chemistry (2017), 60(6), 2573-2590, database is CAplus and MEDLINE.

Glutaminyl cyclase (QC) has been implicated in the formation of toxic amyloid plaques by generating the N-terminal pyroglutamate of β-amyloid peptides (pGlu-Aβ) and thus may participate in the pathogenesis of Alzheimer’s disease (AD). The authors designed a library of glutamyl cyclase (QC) inhibitors based on the proposed binding mode of the preferred substrate, Aβ_3E-42. An in vitro structure-activity relationship study identified several excellent QC inhibitors demonstrating 5- to 40-fold increases in potency compared to a known QC inhibitor. When tested in mouse models of AD, compound 212 (I) significantly reduced the brain concentrations of pyroform Aβ and total Aβ and restored cognitive functions. This potent Aβ-lowering effect was achieved by incorporating an addnl. binding region into the authors’ previously established pharmacophoric model, resulting in strong interactions with the carboxylate group of Glu 327 in the QC binding site. The authors’ study offers useful insights in designing novel QC inhibitors as a potential treatment option for AD.

Journal of Medicinal Chemistry 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, Related Products of pyrimidines.

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

Dolman, Nigel P. published the artcileSynthesis and Pharmacology of Willardiine Derivatives Acting as Antagonists of Kainate Receptors, COA of Formula: C5H6N2O2, the publication is Journal of Medicinal Chemistry (2005), 48(24), 7867-7881, database is CAplus and MEDLINE.

The natural product willardiine, I (R = H), is an AMPA receptor agonist while 5-iodowillardiine, I (R = I), is a selective kainate receptor agonist. In an attempt to produce antagonists of kainate and AMPA receptors, analogs of willardiine with substituents at the N³ position of the uracil ring were synthesized. The N³-4-carboxybenzyl substituted analog II (Ar = C₆H₄CO₂H-4) was found to be equipotent at AMPA and GLU_K5-containing kainate receptors in the neonatal rat spinal cord. The N³-2-carboxybenzyl substituted analog II (Ar = C₆H₄CO₂H-2) proved to be a potent and selective GLU_K5 subunit containing kainate receptor antagonist when tested on native rat and human recombinant AMPA and kainate receptor subtypes. The GLU_K5 kainate receptor antagonist activity was found to reside in the S-enantiomer III (R = H) whereas its R enantiomer was almost inactive. 5-Iodo-substituted derivative III (R = I) was found to have enhanced potency and selectivity for GLU_K5.

Journal of Medicinal 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 C5H6N2O2, COA of Formula: C5H6N2O2.

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

Staedeli, Werner published the artcileNitrogen-15 spectroscopy. Part 5. Nitrogen-15 NMR studies of aminopyridines, aminopyrimidines and of some diazine N-oxides, Formula: C4H6N4O, the publication is Helvetica Chimica Acta (1980), 63(2), 504-22, database is CAplus.

¹⁵N NMR spectra were obtained in neutral and acidic media for mono- and diaminopyridines, and mono-, di-, and triaminopyrimidines. Ring N shifts are discussed in terms of β-, χ-, and δ-substituent effects of amino and alkyl groups. Protonation states in trifluoroacetic acid and FSO₃H solution and protonation effects on the ¹⁵N NMR spectra are determined A linear correlation is observed between amino substituent effects on the ring N-atom in aminopyridines and the corresponding ¹³C values in aminobenzenes, and, similarly, between ¹⁵N values in aminopyrimidines and ¹³C values in aminopyridines. One-bond ¹⁵N-H coupling constants for aminopyridines and aminopyrimidines are discussed in terms of conjugative interaction between NH₂ groups and the ring system.

Helvetica Chimica Acta 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 C11H24O3, Formula: C4H6N4O.

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

Harisha, S. published the artcileClinical trials of water based compositions of active hair growth stimulants in the treatment of alopecia, Computed Properties of 74638-76-9, the publication is European Journal of Biomedical and Pharmaceutical Sciences (2014), 1(3), 284-305, database is CAplus.

Background: Androgenic Alopecia (AGA): Androgenic alopecia (also known as Androgenetic alopecia or Alopecia androgenetica), in male humans in particular this condition is also commonly known as male pattern baldness, hereditary alopecia and simply common baldness. Pathophysiol.: Androgenetic alopecia is a genetically determined disorder and is progressive through the gradual conversion of thick terminal hairs with fine, miniaturized hairs that are eventually lost. Patients with this disorder usually have a typical patterned distribution of hair loss. In Androgenetic alopecia, Studies have indicated a self-renewal of the hair follicle via keratinocyte stem cells located at the area of the bulge of the hair follicle. In addition, a series of studies using mice has indicated that interfollicular keratinocyte stem cells could generate de novo hair follicles in adult mouse skin. These regenerated hair follicles cycled through stages of telogen to anagen. However, these transitions between bulge and epidermal keratinocytes have not been seen yet in human studies. Another report has indicated that mice lacking in functional vitamin D receptors develop a functional first coat of hair, but lack the cyclic regeneration of hair follicles leading to the development alopecia. Whether these findings will lead to a new area of exploration into the cause of Androgenetic alopecia in humans is unknown at this time. Primary objective: To evaluate the Efficacy of topical application of study drug for the treatment of mild to moderate Androgenic Alopecia in Male Patients. Secondary objective: To evaluate the safety of topical application of study drug for the treatment of mild to moderate Androgenic Alopecia in Male Patients. Methods: Subjects were enrolled as per the inclusion and exclusion criteria. All the subjects were then randomized in to 5 different groups. Drug A= FD/SBF/MX-40* Drug B- FD/SBF/PY-39* Drug C- FD/WBF/MX-36* Drug D- FD/WBF/PY-37* Drug E- FD/WBF/KX-38* *Study samples provided by “Kumar Organic Products,Research Center Private Limited”.

European Journal of Biomedical and Pharmaceutical Sciences 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, Computed Properties of 74638-76-9.

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

Brown, D. J. published the artcilePyrimidines. I. Spectroscopic studies, Related Products of pyrimidines, the publication is Journal of the Chemical Society (1953), 331-7, database is CAplus.

Crude 2-chloropyrimidine (I) (2 g.) and NaOMe (from 0.5 g. Na and 25 ml. MeOH) refluxed 0.5 hr., cooled, saturated with CO₂, filtered, the filtrate concentrated in vacuo, the residue extracted with 40 ml. Et₂O, and the dried extract concentrated and distilled gave 0.83 g. 2-methoxypyrimidine (II), colorless liquid, b₁₅ 70-1°, n²⁰_D 1.5060. II (2.4 g.) and 20 ml. 15% Me₂NH-MeOH heated 1 hr. at 120°, NaOMe (from 0.4 g. Na in 20 ml. MeOH) added, and the mixture worked up as above (but without refluxing) gave 1.2 g. 2-(dimethylamino)pyrimidine (III), colorless hygroscopic liquid, b₁₇ 78-81°, n²²_D 1.5438. II and MeNH₂-EtOH similarly gave 2-(methylamino)pyrimidine (IV), b₁₄ 91-2°, m. 59-61° (from petr. ether). 4-Hydroxypyrimidine (V) (7 g.) and 25 ml. POCl₃ refluxed 25 min., cooled, extracted with six 15-ml. portions of petr. ether to remove the POCl₃, and the residue treated with MeOH gave as with II, 4-methoxypyrimidine (VI), colorless liquid, b₃₀ 69-70°. 2,4-Dimercaptopyrimidine (VII) (10.2 g.) and 60 ml. 25% aqueous Me₂NH heated 3 hrs. at 130°, evaporated, the residue treated with 200 ml. cold 0.5N HCl (VII was insoluble), the mixture filtered, and the filtrate adjusted to pH 3-4 gave 8.25 g. 4-dimethylamino-2-mercaptopyrimidine (VIII), m. 265-78° (decomposition), which, treated in 370 ml. boiling H₂O portionwise with 45 g. (wet weight) Raney Ni, refluxed 0.5 hr., filtered hot, the insoluble material washed with 100 ml. hot H₂O, the combined filtrates treated with 20 g. Raney Ni as above, filtered, the filtrate saturated with salt, extracted 15 hrs. with Et₂O, and the extracts concentrated and distilled gave 3.1 g. 4-(dimethylamino)pyrimidine (IX), b₅₀ 131-2°, m. about 40° 2-Mercapto-4-(methylamino)pyrimidine (12 g.) and Raney Ni as above gave 54% 4-(methylamino)pyrimidine (X), b₁₆ 142-4°, m, 69-72° (from petr. ether). 2-Aminopyrimidine (XI) (0.48 g.) and 1.5 ml. Ac₂O refluxed 1 hr., cooled, and 5 ml. Me₂CO added gave 0.45 g. 2-acetamidopyrimidine, colorless laths, m. 145-6.5° [from AcCH₂CHMe (XII)]. 4-Amino-5-cyanopyrimidine (XIII), m. 248-51° (decomposition) (7.4 g.), 55 ml. N KOH, and 225 ml. 3% H₂O₂ kept 1 hr. at 50-5°, the pH adjusted to 7, and the solution cooled gave 5.6 g. 4-amino-5-pyrimidinecarboxamide, colorless laths, m. 254-6° (from H₂O). XIII (1.9 g.) and 19 ml. 2.5N NaOH heated 1 hr. on the steam bath, the pH adjusted to 4, and the whole cooled gave 1.75 g. 4-amino-5 pyrimidinecarboxylic acid (XV), m. 278-81° (from H₂O); XIV (4.25 g.) and 40 ml. 2.5N NaOH gave as above 3.8 g. XV. XV (0.5 g.) added in portions to 5 g. Ph₂CO at 280, kept 5 min. at 280°, cooled to 100°, 25 ml. petr. ether (b. 100-20°) added, and the mixture cooled gave 0.1 g. 4-aminopyrimidine (XVI), m. 150° (from XII); 4-acetamido analog, colorless needles, m. 198-200° (from XII.). The pK_a (for 0.01M solution unless otherwise stated) at 20°, pH (as buffered), λ_maximum and log ε_maximum for the following compounds are reported: V, 1.69 ± 0.04 (or 8.60 ± 0.02), 13 (or 6.2), 227, 263 (or 223, 260), 4.06, 3.56 (or 3.87, 3.57); VI, 2.5 ± 0.2, 6.95 (0), 247-8 (227-8, 238), 3.53 (3.89, 386); XI (0.1M), 3.54, 7.0 (1), 224, 292 (221, 302-3), 4.13, 350 (4.17, 360); IV 3.82, 0.03, 7.0 (1), 234, 306-7 (228, 315), 4.23, 4.33 (4.23, 3.53); III, 3.96 ± 0.01, 7.0 (1), 243, 318 (235, 324-5), 4.26, 3.35 (4.24, 3.47); XVI (0.005M), 5.71, 13 (0), 233, 268-9 (246), 4.26, 3.72 (4.27); X, 6.12 ± 0.04, 9.0 (2.1), 242, 276-7 (254), 4.18, 3.54 (4.20); and IX, 6.35 ± 0.02, 9.3 (3.15), 250, 286 (262), 4.22, 3.56 (4.21). The infrared absorption curves for 2-hydroxypyrimidine, II, V, and VI in CCl₄ are shown; XI and XVI show the 2 strong bands characteristic of the H₂N group, proving that these 2 compounds exist in that form in this solvent. The various spectra are discussed.

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, Related Products of pyrimidines.

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

Fung, B. M. published the artcileDynamic NMR in liquid-crystal solutions. Hindered rotation in 4-(dimethylamino)pyrimidine, Category: pyrimidines, the publication is Journal of the American Chemical Society (1984), 106(24), 7301-4, database is CAplus.

The hindered rotation of the dimethylamino group in 4-(dimethylamino)pyrimidine in a liquid-crystal solution (Merck ZLI 2142) was studied from 232 to 263 K by natural-abundance carbon-13 NMR. The enthalpies of activation were 53, 35, and 52 kJ mol^-1 in the liquid crystal, CD₂Cl₂, and CD₃OD, resp. The ordering forces of the liquid-crystal solvent may favor the planar ground state of the solute more than the bulkier transition state, causing the barrier of rotation to be unusually high.

Journal of the American 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, Category: pyrimidines.

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