Category: pyrimidines

Riand, J. published the artcileMass spectrometry. Induced fragmentation by electron impact of amino and dimethylaminopyrimidines, Recommanded Product: N,N-Dimethylpyrimidin-4-amine, the publication is Journal of Heterocyclic Chemistry (1983), 20(5), 1187-90, database is CAplus.

Fragmentation patterns for I (R = R² = H, R¹ = NH₂; R = R¹ = NH₂, R² = H; R = R¹ = R² = NH₂; R= Me₂N, R¹ = R² = H; R = R² = H, R¹ = Me₂N; R = R¹ = Me₂N, R² = H; R = R¹ = R² = Me₂N) were determined and discussed.

Journal of Heterocyclic 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

Panchaud, Philippe published the artcileDiscovery and Optimization of Isoquinoline Ethyl Ureas as Antibacterial Agents, Computed Properties of 1187931-22-1, the publication is Journal of Medicinal Chemistry (2017), 60(9), 3755-3775, database is CAplus and MEDLINE.

Our strategy to combat resistant bacteria consisted of targeting the GyrB/ParE ATP-binding sites located on bacterial DNA gyrase and topoisomerase IV and not utilized by marketed antibiotics. Screening around the minimal Et urea binding motif led to the identification of isoquinoline Et urea 13 as a promising starting point for fragment evolution. The optimization was guided by structure-based design and focused on antibacterial activity in vitro and in vivo, culminating in the discovery of unprecedented substituents able to interact with conserved residues within the ATP-binding site. A detailed characterization of the lead compound highlighted the potential for treatment of the problematic fluoroquinolone-resistant MRSA, VRE, and S. pneumoniae, and the possibility to offer patients an i.v.-to-oral switch therapy was supported by the identification of a suitable prodrug concept. Eventually, hERG K-channel block was identified as the main limitation of this chem. series, and efforts toward its minimization are reported.

Journal of Medicinal Chemistry published new progress about 1187931-22-1. 1187931-22-1 belongs to pyrimidines, auxiliary class Pyrimidine,Bromide,Salt, name is 4-Bromopyrimidine hydrobromide, and the molecular formula is C4H4Br2N2, Computed Properties of 1187931-22-1.

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

Mahe, Yann published the artcileA minoxidil-related compound lacking a C6 substitution still exhibits strong anti-lysyl hydroxylase activity in vitro, Related Products of pyrimidines, the publication is Skin Pharmacology (1996), 9(3), 177-183, database is CAplus.

It has been previously reported that minoxidil inhibits the activity of lysyl hydroxylase (LH), an enzyme which catalyzes the formation of hydroxylysine, which is necessary for proper maturation of collagen at the transcriptional and enzymic levels. Using the reverse transcriptase-polymerase chain reaction, we confirmed that this inhibition occurred at least at the transcriptional level. Furthermore, we took advantage of this sensitive and rapid method to perform a quant. structure activity relation study using several compounds structurally related to minoxidil. We found that when the C6 of the pyrimidinyl moiety was substituted, it had to be by a tertiary nitrogen, i.e. an N-piperidin ring for the inhibition of LH mRNA synthesis to be observed Surprisingly, however, we found that 2,4-diamino-pyrimidin-3-oxide, a new compound lacking an organic moiety para to the nitroxide oxygen, also retained a high inhibitory effect on LH mRNA expression, comparable to that of minoxidil. We thus conclude that the presence of a substituent para to the nitroxide oxygen is dispensable for inhibition of LH mRNA to be observed in vitro. This brings new insights into the design of therapeutic agents useful in any condition where an overproduction of mature collagen is unwanted, i.e. accelerated wound healing, keloids and localized scleroderma.

Skin Pharmacology 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

Nyeki, A. published the artcileNAT2 and CYP1A2 phenotyping with caffeine: head-to-head comparison of AFMU vs. AAMU in the urine metabolite ratios, HPLC of Formula: 608-34-4, the publication is British Journal of Clinical Pharmacology (2003), 55(1), 62-67, database is CAplus and MEDLINE.

Aims. (i) To compare the phenotyping of healthy subjects for NAT2 (N-acetyltransferase) and CYP1A2 activities with caffeine, by the simultaneous assay of the urinary metabolites AFMU and AAMU, and (ii) to ascertain whether NAT2 and CYP1A2 phenotyping is influenced by the use of AFMU or AAMU in the metabolite ratio. Methods. Thirty-five healthy subjects (16 men, 19 women) participated to the study. Caffeine metabolite concentrations were measured in urine collected 8 h after 2.5 mg kg^-1 caffeine intake using a new validated h.p.l.c. method. The metabolite ratios AFMU/1X, AFMU/(AFMU+1X+1U), AAMU/1X, AAMU/(AAMU+1X+1 U), and (AFMU+1U+1X)/17U, (AAMU+1U+1X)/17U were determined as indexes of NAT2 and CYP1A2 activity, resp. Results. Slow and rapid acetylators were similarly identified using the four NAT2 metabolite ratios in 139 out of 1.40 measurements. An appreciable amount of AAMU was present in urine that was immediately acidified and analyzed. Consequently, the ratio using AFMU was lower than that using total AAMU following transformation of AFMU in basic conditions. The proportion of AFMU in urine analyzed immediately expressed as AFMU/(AFMU+AAMU) ratio did not correlate with urine pH, but was a function of the acetylation phenotype, with a low intergroup variability (64±3% and 32±5%, for rapid and slow acetylators, resp.; P < 0.00001, ANOVA). Regarding CYP1A2 activity, a good correlation (r = 0.99) was observed between the metabolite ratios calculated from AFMU and AAMU, although the ratios calculated from AFMU were proportionately and systematically lower (P < 0.00001, paired t-test, slope 1.2). Conclusions. This study demonstrates that both AFMU and AAMU can be used for NAT2 and CYP1A2 metabolite ratio determinations The reported conversion of AFMU into AAMU is unlikely to explain the large amount of AAMU in urine that was acidified and analyzed immediately after voiding. The results suggest that AAMU is formed not solely through a nonenzymic hydrolysis in urine, but in vivo by a NAT2 phenotype-dependent pathway.

British Journal of Clinical 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, HPLC of Formula: 608-34-4.

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

Scheibe, Christian published the artcileDNA-programmed spatial screening of carbohydrate-lectin interactions, Computed Properties of 169396-92-3, the publication is Chemical Science (2011), 2(4), 770-775, database is CAplus.

A wide range of multivalent scaffolds was assembled by using only five different PNA oligomers and various DNA templates. The flexibility of the PNA-DNA duplexes could be increased by introducing nick-sites and partially unpaired regions, as confirmed by MD simulations. The self-organized glyco-assemblies were used in a spatial screening of accessible carbohydrate binding sites in the Erythrina cristagalli lectin (ECL). This systematic investigation revealed a distance dependence which is in agreement with the crystal structure anal.

Chemical Science 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, Computed Properties of 169396-92-3.

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

Deuss, Peter J. published the artcileParallel synthesis and splicing redirection activity of cell-penetrating peptide conjugate libraries of a PNA cargo, HPLC of Formula: 169396-92-3, the publication is Organic & Biomolecular Chemistry (2013), 11(43), 7621-7630, database is CAplus and MEDLINE.

A novel method for the parallel synthesis of peptide-biocargo conjugates was developed that utilizes affinity purification for fast isolation of the conjugates in order to avoid time consuming HPLC purification The methodol. was applied to create two libraries of cell-penetrating peptide (CPP)-PNA705 conjugates from parallel-synthesized peptide libraries. The conjugates were tested for their ability to induce splicing redirection in HeLa pLuc705 cells. The results demonstrate how the novel methodol. can be applied for screening purposes in order to find suitable CPP-biocargo combinations and further optimization of CPPs.

Organic & Biomolecular 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, HPLC of Formula: 169396-92-3.

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

Deuss, Peter J. published the artcileParallel synthesis and splicing redirection activity of cell-penetrating peptide conjugate libraries of a PNA cargo, Computed Properties of 186046-81-1, the publication is Organic & Biomolecular Chemistry (2013), 11(43), 7621-7630, database is CAplus and MEDLINE.

A novel method for the parallel synthesis of peptide-biocargo conjugates was developed that utilizes affinity purification for fast isolation of the conjugates in order to avoid time consuming HPLC purification The methodol. was applied to create two libraries of cell-penetrating peptide (CPP)-PNA705 conjugates from parallel-synthesized peptide libraries. The conjugates were tested for their ability to induce splicing redirection in HeLa pLuc705 cells. The results demonstrate how the novel methodol. can be applied for screening purposes in order to find suitable CPP-biocargo combinations and further optimization of CPPs.

Organic & Biomolecular 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, Computed Properties of 186046-81-1.

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

Noda, Hidetoshi published the artcileA C4N4 Diaminopyrimidine Fluorophore, COA of Formula: C4H3Cl2N3, the publication is Chemistry – A European Journal (2019), 25(17), 4299-4304, database is CAplus and MEDLINE.

A new scaffold for producing efficient organic fluorescent materials was identified: 2,5-diamino-4,6-diarylpyrimidine featuring a C4N4 elemental composition Single-step installation of two aryl groups at the 4,6-positions of the pyrimidine core delivered fluorescent organic materials in a modular fashion. A range of fluorescent compounds with distinct absorption/emission properties was readily accessed by changing the aromatic attachments. A generally high absorption coefficient and quantum yield were observed, including C4N4 derivatives that could fluoresce even in the solid state. The two amino groups at the 2,5-positions of the pyrimidine were essential for intense fluorescence with a large Stokes shift, which was corroborated by structural relaxation to a p-iminoquinone-like structure in the excited state. Besides live-cell imaging capabilities, fluorescent labeling of a protein involved in autophagy elucidated a new protein-protein interaction, supporting potential utility in bioimaging applications.

Chemistry – A European Journal 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, COA of Formula: C4H3Cl2N3.

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

Bantzi, Marina published the artcileNovel Aryl-Substituted Pyrimidones as Inhibitors of 3-Mercaptopyruvate Sulfurtransferase with Antiproliferative Efficacy in Colon Cancer, Computed Properties of 459420-09-8, the publication is Journal of Medicinal Chemistry (2021), 64(9), 6221-6240, database is CAplus and MEDLINE.

The enzyme 3-mercaptopyruvate sulfurtransferase (3-MST) is one of the more recently identified mammalian sources of H₂S. A recent study identified several novel 3-MST inhibitors with micromolar potency. Among those, (2-[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]-1-(naphthalen-1-yl)ethan-1-one) or HMPSNE was found to be the most potent and selective. Authours now took the central core of this compound and modified the pyrimidone and the arylketone sides independently. A 63-compound library was synthesized; compounds were tested for H₂S generation from recombinant 3-MST in vitro. Active compounds were subsequently tested to elucidate their potency and selectivity. Computer modeling studies have delineated some of the key structural features necessary for binding to the 3-MST’s active site. Six novel 3-MST inhibitors were tested in cell-based assays: they exerted inhibitory effects in murine MC38 and CT26 colon cancer cell proliferation; the antiproliferative effect of the compound with the highest potency and best cell-based activity (2-((2-(Naphthalen-1-yl)-2-oxoethyl)thio)pyrimidin-4(3H)-one) was also confirmed on the growth of MC38 tumors in mice.

Journal of Medicinal Chemistry published new progress about 459420-09-8. 459420-09-8 belongs to pyrimidines, auxiliary class Metabolic Enzyme,3MST, name is 6-Methyl-2-((2-(naphthalen-1-yl)-2-oxoethyl)thio)pyrimidin-4(3H)-one, and the molecular formula is C17H14N2O2S, Computed Properties of 459420-09-8.

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

Neunhoeffer, Hans published the artcileCycloaddition reactions with azabenzenes. X. Cycloaddition reactions with 1,3,5-triazines, Recommanded Product: N,N-Dimethylpyrimidin-4-amine, the publication is Chemische Berichte (1975), 108(12), 3877-82, database is CAplus.

Triazines I (R1, R2, R3 = H, Me, CO2Et, Cl) reacted with electron-rich dienophiles [MeCCNEt2, II, EtOC(NMe2):CHR3 (R3 = H, Me)] and with electron-poor dienophiles (MeO2CCCCO2Me) by a (4+2)-cycloaddition reaction to give pyrimidines III [R4 = R1, R5 = R3, R6 = Me, R7 = NEt2; R4 = R5 = H, R6 = H, CO2Me, R7 = OEt, NMe2, CO2Me; R6R7 = (CH2)3]. I (R3 = Me) reacted with EtOC(NMe2):CHR8 (R8 = H, Me) to give vinyltriazines I [R3 = CH:C(NMe2)CH2R8]. I [R3 = CH:C(NMe2)CH2] reacted with di-Me 1,2,4,5-tetrazine-3,6-dicarboxylate to give pyridazinyltriazines IV.

Chemische Berichte 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