Tag: M.W=100-150

Hennemann, Matthias published the artcileA QSPR-approach to the estimation of the pK_HB of six-membered nitrogen-heterocycles using quantum mechanically derived descriptors, Application of N,N-Dimethylpyrimidin-4-amine, the publication is Journal of Molecular Modeling [online computer file] (2002), 8(4), 95-101, database is CAplus and MEDLINE.

Descriptors derived from semiempirical (AM1) MO calculations have been used to construct a quant. structure-property relationship (QSPR) for the thermodn. hydrogen-bond basicity, pK_HB, of a series of six-membered aromatic nitrogen-heterocycles. The resulting model uses four-descriptors (the Coulson charge on the nitrogen atom, the energy of the localized nitrogen lone-pair orbital, the p-orbital contribution to this MO and an accessibility angle). The model gives r²_ev=0.95 for 51 compounds with a standard deviation between calculation and experiment of 0.13 log units.

Journal of Molecular Modeling [online computer file] 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

Girault, Gisel published the artcileAmino derivatives of several nitrogen-containing heterocycles. II. Preparation, UV absorption, and ionization constants, HPLC of Formula: 31401-45-3, the publication is Bulletin de la Societe Chimique de France (1972), 2787-98, database is CAplus.

Uv spectral data are given ionization constants are determined for pyridines and pyrimidines containing an NH2, NHMe, or NMe2 group, 4-amino-, 4-methylamino-, and 4-dimethylaminoquinoline (I), and the corresponding 9-aminated acridines. Steric inhibition of conjugation is observed for I and 9-dimethylaminoacridine but not for 9-methylaminoacridine.

Bulletin de la Societe Chimique de France 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, HPLC of Formula: 31401-45-3.

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

Ali, Juma A. M. published the artcilePyrimidine salvage in Trypanosoma brucei bloodstream forms and the trypanocidal action of halogenated pyrimidines, Safety of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Molecular Pharmacology (2013), 83(2), 439-453, database is CAplus and MEDLINE.

African trypanosomes are capable of both pyrimidine biosynthesis and salvage of preformed pyrimidines from the host. However, uptake of pyrimidines in bloodstream form trypanosomes has not been investigated, making it difficult to judge the relative importance of salvage and synthesis or to design a pyrimidine-based chemotherapy. Detailed characterization of pyrimidine transport activities in bloodstream form Trypanosoma brucei brucei found that these cells express a high-affinity uracil transporter (designated TbU3) that is clearly distinct from the procyclic pyrimidine transporters. This transporter had low affinity for uridine and 2’deoxyuridine and was the sole pyrimidine transporter expressed in these cells. In addition, thymidine was taken up inefficiently through a P1-type nucleoside transporter. Of importance, the anticancer drug 5-fluorouracil was an excellent substrate for TbU3, and several 5-fluoropyrimidine analogs were investigated for uptake and trypanocidal activity; 5F-orotic acid, 5F-2’deoxyuridine displayed activity in the low micromolar range. The metabolism and mode of action of these analogs was determined using metabolomic assessments of T. brucei clonal lines adapted to high levels of these pyrimidine analogs, and of the sensitive parental strains. The anal. showed that 5-fluorouracil is incorporated into a large number of metabolites but likely exerts toxicity through incorporation into RNA. 5F-2’dUrd and 5F-2’dCtd are not incorporated into nucleic acids but act as prodrugs by inhibiting thymidylate synthase as 5F-dUMP. We present the most complete model of pyrimidine salvage in T. brucei to date, supported by genome-wide profiling of the predicted pyrimidine biosynthesis and conversion enzymes.

Molecular Pharmacology 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, Safety of 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Neidigh, Jonathan W. published the artcileCloning and Characterization of Rhodotorula glutinis Thymine Hydroxylase, Quality Control of 608-34-4, the publication is Chemical Research in Toxicology (2009), 22(5), 885-893, database is CAplus and MEDLINE.

Thymine hydroxylase (TH) is a member of the α-ketoglutarate-dependent nonheme iron dioxygenase family that includes a series of DNA repair proteins including alkB. Substantial interest in this family of enzymes derives from their capacity to modify DNA bases and precursors by oxidation Previously, a sequence has been published for cloned Rhodotorula glutinis TH. However, the minimal reported activity of this enzyme, coupled with inconsistencies with previously published mass spectrometry data, compelled us to reexamine TH. The sequence reported here differs from the previously reported sequence at two amino acid positions and is consistent with previously reported mass spectrometry data. The cloned enzyme characterized in this report displayed substantial activity, indicating that the sequence differences are critical for activity. The substrate selectivity of TH against a series of pyrimidine analogs is consistent with that reported for the wild-type enzyme and, in part, explains the mode of selection of uracil analogs. A preliminary model of the active site has been constructed for the purposes of comparing TH with other members of this family. TH and alkB share in common the capacity to oxidize N-Me groups. However, TH has the added capacity to oxidize the 5-Me group of thymine, a property that is potentially important for enzymes that could act on DNA and modify DNA-protein interactions.

Chemical Research in Toxicology 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, Quality Control of 608-34-4.

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

Kumar, Brajesh published the artcileCoupling 6-chloro-3-methyluracil with copper: structural features, theoretical analysis, and biofunctional properties, Safety of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Dalton Transactions (2021), 50(38), 13533-13542, database is CAplus and MEDLINE.

As nucleobases in RNA and DNA, uracil and 5-methyluracil represent a recognized class of bioactive mols. and versatile ligands for coordination compounds with various biofunctional properties. In this study, 6-chloro-3-methyluracil (Hcmu) was used as an unexplored building block for the self-assembly generation of a new bioactive copper(II) complex, [Cu(cmu)₂(H₂O)₂]·4H₂O (1). This compound was isolated as a stable crystalline solid and fully characterized in solution and solid state by a variety of spectroscopic methods (UV-vis, EPR, fluorescence spectroscopy), cyclic voltammetry, X-ray diffraction, and DFT calculations The structural, topol., H-bonding, and Hirshfeld surface features of 1 were also analyzed in detail. The compound 1 shows a distorted octahedral {CuN₂O₄} coordination environment with two trans cmu^– ligands adopting a bidentate N,O-coordination mode. The monocopper(II) mol. units participate in strong H-bonding interactions with water mols. of crystallization, leading to structural 0D → 3D extension into a 3D H-bonded network with a tfz-d topol. Mol. docking and ADME anal. as well as antibacterial and antioxidant activity studies were performed to assess the bioactivity of 1. In particular, this compound exhibits a prominent antibacterial effect against Gram neg. (E. coli, P. aeruginosa) and pos. (S. aureus, B. cereus) bacteria. The obtained copper(II) complex also represents the first structurally characterized coordination compound derived from 6-chloro-3-methyluracil, thus introducing this bioactive building block into a family of uracil metal complexes with notable biofunctional properties.

Dalton Transactions 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, Safety of 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Trüeb, R M published the artcile[Status of scalp hair and therapy of alopecia in men in Switzerland]., SDS of cas: 74638-76-9, the publication is Praxis (2001), 90(7), 241-8, database is MEDLINE.

A community-based interview and a questionnaire of men visiting the dermatologist for treatment of hair loss were conducted in Switzerland, to characterize the significance of scalp hair and self-perception of hair loss in Swiss men, and to evaluate current treatment of hair loss. 508 men, aged 15-74 years, regardless of the degree of hair loss, were interviewed by telephone, and 308 patient questionnaires were completed by 19 dermatologists. The questions addressed by the interview were: degree of self-rated hair loss, time invested for hair care, use or reasons for rejecting hair growing agents, relevant criteria for scalp hair, self-assessment with respect to different “hair communication types”. The questionnaire analysed the causes of hair loss, prior and current treatment modalities, and follow-up at the dermatologist. Respondents rated their hair loss on a 5-point, textual scale that ranged from ‘no hair loss’ to ‘bald areas’. 43% reported hair loss to some extent. For 42% a full head of hair was very important, especially for men under 29 years, who invested more time for hair care and had not lost hair. Of men with hair loss, 26% previously applied hair growing agents. Of men consulting the dermatologist for hair loss, 90% had androgenetic alopecia. 37% were previously treated: prior treatment was in 59% minoxidil, in 4% finasteride (Propecia), in 7% Aminexil, in 7% dietary supplements, and in 6% conducted by the hair dresser. In 79% treatment was switched to Propecia: of these, 73% adhered to the follow-up consultations at the dermatologist.

Praxis 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 C18H28N2O7, SDS of cas: 74638-76-9.

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

Tang, Qi published the artcileCharacterization of Byproducts from Chemical Syntheses of Oligonucleotides Containing 1-Methyladenine and 3-Methylcytosine, Category: pyrimidines, the publication is ACS Omega (2017), 2(11), 8205-8212, database is CAplus and MEDLINE.

Oligonucleotides serve as important tools for biol., chem., and medical research. The preparation of oligonucleotides through automated solid-phase synthesis is well established. However, identification of byproducts generated from DNA synthesis, especially from oligonucleotides containing site-specific modifications, is sometimes challenging. Typical HPLC, Mass Spectrometry (MS), and gel electrophoresis methods alone are not sufficient for characterizing unexpected byproducts, especially for those having identical or very similar mol. weight (MW) to the products. The authors used a rigorous quality control procedure to characterize byproducts generated during oligonucleotide syntheses: (1) purify oligonucleotide by different HPLC systems; (2) determine the exact MW by high resolution MS; (3) locate modification position by MS/MS or exonuclease digestion with MALDI-TOF anal.; and (4) conduct, where applicable, enzymic assays. The authors applied these steps to characterize byproducts in the syntheses of oligonucleotides containing important Me DNA adducts 1-methyladenine (m1A) and 3-methylcytosine (m3C). In m1A synthesis, the authors differentiated a regioisomeric byproduct 6-methyladenine, which possesses identical MW to m1A. As for m3C, the authors identified a deamination byproduct 3-methyluracil, which is only 1 Da greater than m3C in the ∼ 4900 Da context. The detection of these byproducts would be very challenging if the abovementioned procedure were not adopted.

ACS Omega 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 C14H12N2S, Category: pyrimidines.

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

Rapp, Magdalena published the artcileReactions of trimethylsilyl fluorosulfonyldifluoroacetate with purine and pyrimidine nucleosides, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of Fluorine Chemistry (2009), 130(3), 321-328, database is CAplus and MEDLINE.

Difluorocarbene, generated from trimethylsilyl fluorosulfonyldifluoroacetate (TFDA), reacts with the uridine and adenosine substrates preferentially at the enolizable amide moiety of the uracil ring and the 6-amino group of the purine ring. 2′,3′-Di-O-benzoyl-3′-deoxy-3′-methyleneuridine reacts with TFDA to produce 4-O-difluoromethyl product derived from an insertion of difluorocarbene into the 4-hydroxyl group of the enolizable uracil ring. Reaction of the difluorocarbene with the adenosine substrates having the unprotected 6-amino group in the purine ring produced the 6-N-difluoromethyl derivative, while reaction with 6-N-benzoyl protected adenosine analogs gave the difluoromethyl ether product derived from the insertion of difluorocarbene into the enol form of the 6-benzamido group. Treatment of the 6-N-phthaloyl protected adenosine analogs with TFDA resulted in the unexpected one-pot conversion of the imidazole ring of the purine into the corresponding N-difluoromethylthiourea derivatives Treatment of the suitably protected pyrimidine and purine nucleosides bearing an exo-methylene group at carbons 2′, 3′ or 4′ of the sugar rings with TFDA afforded the corresponding spiro-difluorocyclopropyl analogs but in low yields.

Journal of Fluorine 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, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Wang, Binju published the artcileComputations Reveal a Rich Mechanistic Variation of Demethylation of N-Methylated DNA/RNA Nucleotides by FTO, HPLC of Formula: 608-34-4, the publication is ACS Catalysis (2015), 5(12), 7077-7090, database is CAplus.

The fat-mass and obesity-associated (FTO) protein employs an iron(IV) oxo species to demethylate N-methylated nucleic acids. Herein, we use atomistic-theor. calculations to study the demethylation of the N-methylated DNA/RNA bases 6-methylated adenine (m⁶A), 3-methylated thymine (m³T), and 3-methylated uracil (m³U). The mechanisms involve in-enzyme hydroxylation of the Me group, followed by hydrolysis of the oxidized intermediates in aqueous solution to demethylate the bases. The in-enzyme reactions have been studied using quantum mech./mol. mech. (QM/MM) calculations, while the hydrolytic reactions occurring outside the enzyme have been explored with hybrid cluster-continuum (HCC) calculations When the results obtained with these different methods are combined, the calculated barrier for the overall transformation is consistent with the exptl. free energy barrier for the major route of m⁶A demethylation: in this pathway, adenine’s N1 site acts as an internal base catalyst in the rate-determining hydrolysis of the hydroxylated hemiaminal intermediate hm⁶A to a demethylated A and formaldehyde. This N1-catalyzed mechanism makes m⁶A the most reactive substrate in comparison to other bases we tested. In the minor, slower, route, two oxidation steps by FTO generate an amide intermediate (f⁶A) that undergoes in-water hydrolysis, producing A and formic acid, as found exptl. In contrast, since m³T and m³U lack internal basic catalytic sites, their hemiaminals decompose with high barriers. The mechanism instead involves two sequential oxidations, leading to demethylated bases and formic acid. Thus, our results, obtained using a holistic approach combining modeling the enzyme and the surrounding aqueous solution, suggest revisions of the exptl. mechanisms for m³T and m³U demethylation.

ACS Catalysis 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 C50H65O4P, HPLC of Formula: 608-34-4.

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

Segado, Mireia published the artcileUnderstanding the differences in photochemical properties of substituted aminopyrimidines, Product Details of C6H9N3, the publication is Theoretical Chemistry Accounts (2011), 128(4-6), 713-725, database is CAplus.

The luminescent patterns of several members of the aminopyrimidine family are very different, showing not fluorescence at all, only a fluorescence band, normal or anomalous, or dual fluorescence, depending on the substituents and on the environment (gas phase vs. polar solvents). The authors study the lowest excited states of several members of this family that exhibit different fluorescence patterns to try to explain their photochem. and to understand the effect of the substituents and the environment. Several excited states (local excited (LE), charge transfer (CT) and n _N-π^* states) have min. on the lowest excited potential energy surface (S₁), being their relative energy the determinant factor of the luminescent behavior. If the more stable S₁ min. are of n _N-π^* character, a nonradiative deexcitation channel is the most efficient and the system shows no fluorescence. If the CT and/or LE states are the most stable, the nonradiative deactivation channel is not accessible and the system fluoresces. The relative energies of the CT and LE min. (affected by substituents and by the presence of a polar solvent) and the different magnitude of the oscillator strength for the radiative transition to the ground state determine which emission is more efficient, giving place to normal, anomalous or dual fluorescence. The study was carried out by CASSCF/CASPT2 computations, including the solvent effect by the PCM model.

Theoretical Chemistry Accounts 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 C9H21NO3, Product Details of C6H9N3.

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