Month: November 2022

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

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

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

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

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

Saleh, Amer F. published the artcileSynthesis and Splice-Redirecting Activity of Branched, Arginine-Rich Peptide Dendrimer Conjugates of Peptide Nucleic Acid Oligonucleotides, Computed Properties of 186046-81-1, the publication is Bioconjugate Chemistry (2010), 21(10), 1902-1911, database is CAplus and MEDLINE.

Arginine-rich cell-penetrating peptides have found excellent utility in cell and in vivo models for enhancement of delivery of attached charge-neutral PNA or PMO oligonucleotides. The authors report the synthesis of dendrimeric peptides containing 2- or 4-branched arms each having one or more R-Ahx-R (R = Arg; Ahx = aminohexanoic acid) motifs and their disulfide conjugation to a PNA705 splice-redirecting oligonucleotide. Conjugates were assayed in a HeLa pLuc705 cell assay for luciferase up-regulation and splicing redirection. Whereas 8-Arg branched peptide-PNA conjugates showed poor activity compared to a linear (R-Ahx-R)₄-PNA conjugate, 2-branched and some 4-branched 12 and 16 Arg peptide-PNA conjugates showed activity similar to that of the corresponding linear peptide-PNA conjugates. Many of the 12- and 16-Arg conjugates retained significant activity in the presence of serum. Evidence showed that biol. activity in HeLa pLuc705 cells of the PNA conjugates of branched and linear (R-Ahx-R) peptides is associated with an energy-dependent uptake pathway, predominantly clathrin-dependent, but also with some caveolae dependence.

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 C39H35N5O8, Computed Properties of 186046-81-1.

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

Saleh, Amer F. published the artcileSynthesis and Splice-Redirecting Activity of Branched, Arginine-Rich Peptide Dendrimer Conjugates of Peptide Nucleic Acid Oligonucleotides, Safety of 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 Bioconjugate Chemistry (2010), 21(10), 1902-1911, database is CAplus and MEDLINE.

Arginine-rich cell-penetrating peptides have found excellent utility in cell and in vivo models for enhancement of delivery of attached charge-neutral PNA or PMO oligonucleotides. The authors report the synthesis of dendrimeric peptides containing 2- or 4-branched arms each having one or more R-Ahx-R (R = Arg; Ahx = aminohexanoic acid) motifs and their disulfide conjugation to a PNA705 splice-redirecting oligonucleotide. Conjugates were assayed in a HeLa pLuc705 cell assay for luciferase up-regulation and splicing redirection. Whereas 8-Arg branched peptide-PNA conjugates showed poor activity compared to a linear (R-Ahx-R)₄-PNA conjugate, 2-branched and some 4-branched 12 and 16 Arg peptide-PNA conjugates showed activity similar to that of the corresponding linear peptide-PNA conjugates. Many of the 12- and 16-Arg conjugates retained significant activity in the presence of serum. Evidence showed that biol. activity in HeLa pLuc705 cells of the PNA conjugates of branched and linear (R-Ahx-R) peptides is associated with an energy-dependent uptake pathway, predominantly clathrin-dependent, but also with some caveolae dependence.

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 C26H26N4O7, Safety of 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

Della Sala, Giorgio published the artcileSynthesis of uracil derivatives by oxidation of Fischer tungsten-carbene uracil complexes, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of Organometallic Chemistry (2007), 692(8), 1623-1627, database is CAplus.

A study on the oxidation of Fischer tungsten-carbene uracil complexes has been carried out. E.g., oxidation of Fischer tungsten-carbene uracil complex I by Me₃NO gave 78% uracil II. Several commonly used oxidants gave results strongly influenced by the presence of substituents on the nitrogen atoms. In particular, the usual oxidants failed in the oxidation of 3-alkyl uracil carbene complexes. Finally, the authors showed that t-Bu hydroperoxide is able to oxidize successfully 3-alkyl uracil carbene complexes and can be used as a good alternative to the other methods.

Journal of Organometallic 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, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Krchnak, V. published the artcileNovel pyrimidine derivatives, reactions, and ultraviolet spectra, Name: 5-Aminopyrimidine-2-carbonitrile, the publication is Collection of Czechoslovak Chemical Communications (1975), 40(5), 1396-402, database is CAplus.

The conditions were studied for selective hydrolysis of I (R1 = NH2, NMe2, OH, OAc, OMe, SH, SMe, H, F, Cl, Br, SOME2, SO2Me, CN) and the products characterized by uv spectra. Hydrolysis of I in boiling 0.02M H2SO4 or 0.2M AcOH gave the corresponding II, while treating I with 0.2M H2SO4 at 110° or with boiling 5% K2CO3 solution yielded the appropriate III. In strongly alk. media I (R1 = CN) gave III (R1 = CONH2) and III (R1 = CO2H). Special conditions were required for the hydrolysis of I (R1 = F) (IV) which gave in 3M KHF2 at 75° II (R1 = F) and at 120° afforded III (R1 = F), while heating IV in 5% K2CO3 solution yielded III (R1 = NMe2).

Collection of Czechoslovak Chemical Communications 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 C5H4N4, Name: 5-Aminopyrimidine-2-carbonitrile.

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

Krchnak, V. published the artcilePreparation and some reactions of 2,5-substituted pyrimidines, Synthetic Route of 56621-93-3, the publication is Collection of Czechoslovak Chemical Communications (1975), 40(5), 1384-9, database is CAplus.

The title compounds I (X = H, NH2, SH, SMe) were prepared by direct synthesis from [Me2NCH:C(CH:NMe2)N:CHNMe2]+ClO4- and HN:CXNH2. The reactants were reluxed in EtOH with dropwise addition of MeONa and HNEt2 distilled off in vacuo. I (X = H) was accompanied by [Me2NCH:NCH:NMe2]+ClO4- as by-product formed by reaction of liberated HNMe2 with HN:CHNH2. I (X = SMe) gave with NaClO, according to the reaction temperature, I (X = SOMe) or I (X = SO2Me) (II). II was especially ready for nucleophilic substitution of the SO2Me group and gave with alc. MeONa and with KCN in hot DMF, resp., I (X = OMe) and I (X = CN). Reaction of I (X = SH) with Me2SO in the presence of H2SO4 yielded III instead of the expected 2-hydroxypyrimidine derivative The readiness of II to undergo nucleophilic substitution by OMe and CN in the position 2 was compared with 3 addnl. 2-methylsulfonylpyrimidine 5-substituted with NHCHO, NH2, and H. The reaction rate was lowered by electron donating 5-substituents but the order of reactivities was different for OMe and CN.

Collection of Czechoslovak Chemical Communications 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 C5H4N4, Synthetic Route of 56621-93-3.

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