Category: pyrimidines

Bowler, Frank R. published the artcileDNA Analysis by Dynamic Chemistry, Name: 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, the publication is Angewandte Chemie, International Edition (2010), 49(10), 1809-1812, S1809/1-S1809/29, database is CAplus and MEDLINE.

Herein we report the application of dynamic chem. to DNA anal., offering the prospect of nonenzymic genotyping of genomic DNA amplified by polymerase chain reaction (PCR). This was achieved by the synthesis of a PNA strand that contained a blank position opposite the nucleobase under anal. in a complementary DNA template. A reversible reaction, between this PNA/DNA duplex (specifically the secondary amine of the “PNA blank”) and four aldehyde-modified nucleobases, means that the templating power of Watson-Crick base pairing and base stacking would be expected to drive the selection of the fully complementary iminium nucleobase. Subsequent reduction and MALDI-TOF mass spectrometry would allow rapid determination of base incorporation.

Angewandte Chemie, International Edition 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, Name: 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid.

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

Prakash, Anjanappa published the artcileEfficient indoles and anilines syntheses employing tert-butyl sulfinamide as ammonia surrogate, Application of 5-Aminopyrimidine-2-carbonitrile, the publication is Tetrahedron Letters (2011), 52(43), 5625-5628, database is CAplus.

Tert-Bu sulfinamide is an ammonia equivalent for the palladium-catalyzed amination of aryl bromides and aryl chlorides. Using these amine derivatives, it has been observed that substituted indoles and anilines with sensitive functional groups can be readily prepared This surrogate has also been used for the synthesis of indoles from (2-bromophenyl)ethynes using palladium-catalyzed cross coupling reaction as the key step.

Tetrahedron Letters 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, Application of 5-Aminopyrimidine-2-carbonitrile.

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

Ascencao, Kelly published the artcilePharmacological induction of mesenchymal-epithelial transition via inhibition of H₂S biosynthesis and consequent suppression of ACLY activity in colon cancer cells, Name: 6-Methyl-2-((2-(naphthalen-1-yl)-2-oxoethyl)thio)pyrimidin-4(3H)-one, the publication is Pharmacological Research (2021), 105393, database is CAplus and MEDLINE.

Hydrogen sulfide (H₂S) is an important endogenous gaseous transmitter mediator, which regulates a variety of cellular functions in autocrine and paracrine manner. The enzymes responsible for the biol. generation of H₂S include cystathionine-β-synthase (CBS), cystathionine-γ-lyase (CSE) and 3-mercaptopyruvate sulfurtransferase (3-MST). Increased expression of these enzymes and overproduction of H₂S has been implicated in essential processes of various cancer cells, including the stimulation of metabolism, maintenance of cell proliferation and cytoprotection. Cancer cell identity is characterized by so-called “transition states”. The progression from normal (epithelial) to transformed (mesenchymal) state is termed epithelial-to-mesenchymal transition (EMT) whereby epithelial cells lose their cell-to-cell adhesion capacity and gain mesenchymal characteristics. The transition process can also proceed in the opposite direction, and this process is termed mesenchymal-to-epithelial transition (MET). The current project was designed to determine whether inhibition of endogenous H₂S production in colon cancer cells affects the EMT/MET balance in vitro. Inhibition of H₂S biosynthesis in HCT116 human colon cancer cells was achieved either with aminooxyacetic acid (AOAA) or 2-[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]-1-(naphthalen-1-yl)ethan-1-one (HMPSNE). These inhibitors induced an upregulation of E-cadherin and Zonula occludens-1 (ZO-1) expression and downregulation of fibronectin expression, demonstrating that H₂S biosynthesis inhibitors can produce a pharmacol. induction of MET in colon cancer cells. These actions were functionally reflected in an inhibition of cell migration, as demonstrated in an in vitro “scratch wound” assay. The mechanisms involved in the action of endogenously produced H₂S in cancer cells in promoting (or maintaining) EMT (or tonically inhibiting MET) relate, at least in part, in the induction of ATP citrate lyase (ACLY) protein expression, which occurs via upregulation of ACLY mRNA (via activation of the ACLY promoter). ACLY in turn, regulates the Wnt-β-catenin pathway, an essential regulator of the EMT/MET balance. Taken together, pharmacol. inhibition of endogenous H₂S biosynthesis in cancer cells induces MET. We hypothesize that this may contribute to anti-cancer / anti-metastatic effects of H₂S biosynthesis inhibitors.

Pharmacological Research 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, Name: 6-Methyl-2-((2-(naphthalen-1-yl)-2-oxoethyl)thio)pyrimidin-4(3H)-one.

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

Feuerstein, Marie published the artcileSonogashira reaction of heteroaryl halides with alkynes catalyzed by a palladium-tetraphosphine complex, SDS of cas: 174456-28-1, the publication is Journal of Molecular Catalysis A: Chemical (2006), 256(1-2), 75-84, database is CAplus.

Cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/(1/2)[PdCl(C₃H₅)]₂ system catalyzes the Sonogashira reaction of heteroaryl halides with a range of alkynes with moderate to high substrate/catalyst ratios in good yields. A variety of heteroaryl halides such as pyridines, quinolines, a pyrimidine, an indole, thiophenes, or a thiazole have been used successfully. The reaction also tolerates several alkynes such as phenylacetylene and alk-1-ynols. The nature of the heteroaromatics and the substituent of the alkynes have both an important effect on the reaction rates. High reaction rates were generally observed with phenylacetylene. With this alkyne substrate/catalyst ratios up to 10,000 have been used successfully. An effect of the position of the alc. function on the reaction rates was observed with alk-1-ynols. Higher substrate/catalyst ratios could be used with but-3-yn-1-ol, pent-4-yn-1-ol or hex-5-yn-1-ol than with propargyl alc. The nature and the position of the halide on the heteroaromatics have also an important effect on the reaction rates. As expected, higher reaction rates were obtained with heteroaryl iodides than with heteroaryl bromides or chlorides.

Journal of Molecular Catalysis A: Chemical 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, SDS of cas: 174456-28-1.

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

Kovackova, Sona published the artcileThe synthesis of piperidine nucleoside analogs-a comparison of several methods to access the introduction of nucleobases, Formula: C4H3Cl2N3, the publication is Tetrahedron (2011), 67(7), 1485-1500, database is CAplus.

This work deals with the synthesis of piperidine and hydroxypiperidine analogs of nucleosides, e.g. I. Starting from com. available 3-hydroxypiperidine, proline or 4-hydroxyproline, a series of piperidine derivatives of both purine and pyrimidine nucleobases was prepared Various methods of nucleobase attachment were evaluated. The prepared compounds were tested for cytostatic, antibacterial, and antiviral properties but no significant activity was found.

Tetrahedron 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, Formula: C4H3Cl2N3.

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

Ackermann, H. published the artcileConstitution and reactivity of trichloropyrimidylamino derivatives, Category: pyrimidines, the publication is Helvetica Chimica Acta (1962), 1683-98, database is CAplus.

The treatment of 2,4,5,6-tetrachloropyrimidine (I) with NH₃, aliphatic, and aromatic amines resulted almost exclusively in reaction of the 4-Cl atom. The kinetics of the reaction of 2,5,6-trichloro-4-pyrimidylamino derivatives with NaOEt was studied. The derivatives from primary aromatic amines were found to be weak acids, which explained the relationship between constitution and reactivity satisfactorily. PhNH₂ (9.3 g.) in 50 cc. Me₂CO and 50 cc. H₂O heated at 35-40° with 21.8 g. I while maintaining pH 6-7 by the dropwise addition of 20% aqueous Na₂CO₃, heated briefly to 50°, and cooled to 0-5° yielded 86% 4-anilino-2,5,6-trichloropyrimidine (II), m. 83-4° (ligroine). Similarly were prepared the following 4-substituted-2,5,6-trichloropyrimidines (4-substituent, reaction temperature, and m.p. given): p-ClC₆H₄NH (III), 40-50°, 153° (ligroine); o-MeOC₆H₄NH, 40-50°, 183° (C₆H₆); MePhN (IV), 35-40°, 118° (AcOH); p-MeC₆H₄NH, 35-40°, 111° (ligroine); p-MeOC₆H₄NH (V), 35-40°, 129° (ligroine); o-MeC₆H₄NH, 40-50°, 139° (C₆H₆); o-ClC₆H₄NH, 4050°, 158° (C₆H₆); m-HO₃SC₆H₄NH (VI), 40-50%, – (precipitated with KNO₃ as the K salt); m-HO₂CC₆H₄NH, 40-50°, 246° (AcOH); p-O₂NC₆H₄NMe (VII), 85-90° (in aqueous dioxane), 210° (PhCl); p-HOC₆H₄NH (VIII), 30-40°, 112° (C₆H₆); o-HOC₆H₄NH, 40-50°, 216° (EtOH); p-MeO₂SC₆H₄NH (IX), 40-50°, 225° (PhCl); p-O₂NC₆H₄NH (X), 40-50°, 204° (MePh). II (27.5 g.) in 400 cc. concentrated NH₄OH heated 20 hrs. at 110-20° in an autoclave and cooled gave 2,6-diamino-4-anilino-5-chloropyrimidine (XI), m. 218° (MeOCH₂CH₂OH). XI (4.4 g.) in 150 cc. MeOH containing 4.4 g. NaOAc hydrogenated 3 days at room temperature and low pressure, filtered, neutralized with Na₂CO₃, concentrated, diluted with H₂O, and filtered gave 2,6-diamino-4-anilinopyrimidine, m. 177-8° (EtOH), also obtained from 2,4-diamino-6-chloropyrimidine and PhNH₂. BuNH₂ (7.3 g.) in 125 cc. Me₂CO and 125 cc. H₂O treated during 1 hr. at 30-5° with 21.8 g. I at pH 10-11 and extracted with Et₂O yielded 4-butylamino-2,5,6-trichloropyrimidine (XII), b₁₄ 187-8°, m. 62-5°. Similarly was prepared the 4-Et₂N analog (XIII) of XII, b₈ 174-5°, m. 50-1°; the forerun yielded a small amount of 2-diethylamino-4,5,6-trichloropyrimidine, b₈ 152-3°, m. 768°. I (21.8 g.) in 150 cc. concentrated NH₄OH stirred 2 hrs. at 80° and cooled gave 4-amino-2,5,6-trichloropyrimidine, m. 168° (PhCl). II (27.5 g.) in 100 cc. absolute EtOH treated dropwise with 4.0 g. KOH in 100 cc. EtOH, heated 2 hrs. at 70°, filtered, and cooled gave 4-anilino-2,5-dichloro5-ethoxypyrimidine (XIV), m. 124° (EtOH); the alc. mother liquor gave 4-anilino-5,6-dichloro-2-ethoxypyrimidine (XV), m. 66° (ligroine). 2,4-Dichloropyrimidine (14 g.) in 100 cc. Me₂CO and 100 cc. H₂O treated at 40-50° with 9.3 g. PhNH₂ at pH 6-7, cooled to 0-5°, filtered, the residue recrystallized from PhCl, refluxed 4 hrs. with 1 equivalent KOH in 200 cc. EtOH, diluted with H₂O, and filtered yielded 4-anilino-2-ethoxypyrimidine (XVI), m. 121-2° (ligroine). XV (2.84 g.) in 150 cc. absolute EtOH and 2.2 g. Et₃N hydrogenated 21 hrs. at room temperature over 5 g. Pd-C also yielded XVI. XIV gave similarly 4-anilino-6-ethoxypyrimidine, m. 122-3°. II (27.5 g.) and 4.6 g. Na in 200 cc. absolute EtOH refluxed 3 hrs. gave 4-anilino-5-chloro-2,6-diethoxypyrimidine, m. 131° (EtOH). The appropriate compound (6.23 × 10^-3 moles) in 400 cc. absolute EtOH treated at the desired temperature with 100 cc. 1.25N NaOH and the liberated chloride determined titrimetrically in 20-cc. aliquots gave the ks × 10⁵ values (determined at 30°) for the following compounds: 4-methylphenylamino-2,6-dichloro-1,3,5-triazine, above 1000; 4-methylphenylamino-2-amino-6-chloro-1,3,5-triazine, 17; 4-methylphenylamino-2,6-dichloropyrimidine, 9.3; IV, 310; VII, above 500; XIII, 31. The pK values were determined for the following compounds: VI (Na salt), 11.6; 4-(msulfanilino)-2,6-dichloropyrimidine (Na salt), 13.0; 4-(msulfanilino)-2,6-dichloro-1,3,5-triazine (Na salt), 11.2; 4-(m-sulfanilino)-2-amino-6-chloro-1,3,5-triazine (Na salt), 13.8. The ks × 10⁵ (at 30°), k₃ × 10⁴ (at 70°), and k₄ × 10⁴ (at 70°) values (given in this order) were determined in the usual manner for the following compounds: 2-anilino-4,6-dichloro-1,3,5-triazine, 350, -, -; 2-amino-4-anilino-6-chloro-1,3,5-triazine, 37, -, -; 4-anilino-2,6-dichloropyrimidine, 2.2, 0.38, 0.22; II, 1.3, 1.8, 1.2. The ks × 10⁵ (given) were determined at 70° in the usual manner for the following compounds: II, 41; VIII, 210; o-isomer of VIII, 170; V, 49; o-isomer of V, 180; III, 21; o-isomer of III, 15; IX, 6; X, about 5.M

Helvetica Chimica Acta 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

Gerhardt, Valeska published the artcileCocrystals of 6-chlorouracil and 6-chloro-3-methyluracil: exploring their hydrogen-bond-based synthon motifs with several triazine and pyrimidine derivatives, SDS of cas: 608-34-4, the publication is Acta Crystallographica, Section B: Structural Science, Crystal Engineering and Materials (2015), 71(2), 209-220, database is CAplus and MEDLINE.

In order to obtain complexes held together by hydrogen as well as halogen bonds, 6-chlorouracil [6-chloropyrimidin-2,4(1H,3H)-dione; 6CU] and its 3-Me derivative [6-chloro-3-methylpyrimidin-2,4(1H,3H)-dione; M6CU] were cocrystd. with 2,4,6-triaminopyrimidine and the three triazine derivatives 2,4,6-triamino-1,3,5-triazine (melamine), 2,4-diamino-6-methyl-1,3,5-triazine and 2-chloro-4,6-diamino-1,3,5-triazine, which all offer complementary hydrogen-bonding sites. Three of these compounds form cocrystals with 6CU; however, melamine yielded only a new pseudopolymorph with 6CU, but formed a cocrystal with M6CU. All six cocrystals contain solvent mols. (N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidin-2-one), whose intermol. interactions contribute significantly to the stabilization of the crystal packing. Each of these structures comprises chains, which are primarily formed by strong hydrogen bonds with a basic framework built by R ₂ ²(8) hydrogen bonds of either pure N-H···N or mixed patterns. Solvent mols. are aligned to the border of these chains via N-H···O hydrogen bonds. Two of the reported crystal structures containing 6CU show addnl. Cl···O halogen bonds, which connect the chains to two-dimensional layers, while one weak and one strong Cl···Cl interaction are observed in the two structures in which mols. of M6CU are present.

Acta Crystallographica, Section B: Structural Science, Crystal Engineering and Materials 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, SDS of cas: 608-34-4.

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

Javaid, Z. Z. published the artcilePyrimidine nucleobase ligands of orotate phosphoribosyltransferase from Toxoplasma gondii, SDS of cas: 608-34-4, the publication is Biochemical Pharmacology (1999), 58(9), 1457-1466, database is CAplus and MEDLINE.

Sixty-seven pyrimidine nucleobase analogs were evaluated as ligands of Toxoplasma gondii orotate phosphoribosyltransferase (OPRTase, EC 2.4.2.10) by measuring their ability to inhibit this enzyme in vitro. Apparent Ki values were determined for compounds that inhibited T. gondii OPRTase by greater than 20% at a concentration of 400 μM. 1-Deazaorotic acid (0.47 μM) and 5-azaorotic acid (2.1 μM) were found to bind better (8.3- and 1.9-fold, resp.) to T. gondii OPRTase than orotic acid, the natural substrate of the enzyme. Based on these results, a structure-activity relationship of ligand binding to OPRTase was formulated using uracil, barbituric acid, and orotic acid as reference compounds It was concluded that the following structural features of pyrimidine nucleobase analogs were required or strongly preferred for binding: (i) an endocyclic pyridine-type nitrogen or methine at the 1-position; (ii) exocyclic oxo groups at the 2- and 4-positions; (iii) a protonated endocyclic pyridine-type nitrogen at the 3-position; (iv) an endocyclic pyridine-type nitrogen or methine at the 5-position; (v) an exocyclic hydrogen or fluorine at the 5-position; (vi) an endocyclic pyridine-type nitrogen or methine at the 6-position; and (vii) an exocyclic neg. charged or electron-withdrawing group at the 6-position. A comparison of the results from the present study with those from a previous study on mammalian OPRTase [Niedzwicki et al., Biochem Pharmacol 33: 2383-2395, 1984] identified four compounds (6-chlorouracil, 5-azaorotic acid, 1-deazaorotic acid, and 6-iodouracil) that may bind selectively to T. gondii OPRTase.

Biochemical 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, SDS of cas: 608-34-4.

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

Brun, Omar published the artcileOn-Resin Conjugation of Diene-Polyamides and Maleimides via Diels-Alder Cycloaddition, Synthetic Route of 169396-92-3, the publication is Journal of Organic Chemistry (2015), 80(12), 6093-6101, database is CAplus and MEDLINE.

The reaction between maleimides and resin-bound diene-polyamides (polyamides are represented by peptides and peptide nucleic acids or PNAs) allows the latter to be used in the preparation of conjugates. Conjugation takes place by reacting the insoluble, hydrophobic diene component either with water-soluble dienophiles or with dienophiles requiring mixtures of water and organic solvents. Exptl. conditions can be adjusted to furnish the target conjugate in good yield with no need of adding large excesses of soluble reagent. In case protected maleimides are used, maleimide deprotection and Diels-Alder cycloaddition can be simultaneously carried out to render conjugates with different linking positions. On-resin conjugation is followed by an acidic treatment that removes the polyamide protecting groups with no harm to the cycloadduct, in contrast with the unreacted diene that is indeed degraded under these conditions. Cycloadducts incorporating suitable functional groups can undergo subsequent addnl. conjugation reactions in solution to furnish double conjugates.

Journal of Organic 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, Synthetic Route of 169396-92-3.

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

Brun, Omar published the artcileOn-Resin Conjugation of Diene-Polyamides and Maleimides via Diels-Alder Cycloaddition, COA of Formula: C39H35N5O8, the publication is Journal of Organic Chemistry (2015), 80(12), 6093-6101, database is CAplus and MEDLINE.

The reaction between maleimides and resin-bound diene-polyamides (polyamides are represented by peptides and peptide nucleic acids or PNAs) allows the latter to be used in the preparation of conjugates. Conjugation takes place by reacting the insoluble, hydrophobic diene component either with water-soluble dienophiles or with dienophiles requiring mixtures of water and organic solvents. Exptl. conditions can be adjusted to furnish the target conjugate in good yield with no need of adding large excesses of soluble reagent. In case protected maleimides are used, maleimide deprotection and Diels-Alder cycloaddition can be simultaneously carried out to render conjugates with different linking positions. On-resin conjugation is followed by an acidic treatment that removes the polyamide protecting groups with no harm to the cycloadduct, in contrast with the unreacted diene that is indeed degraded under these conditions. Cycloadducts incorporating suitable functional groups can undergo subsequent addnl. conjugation reactions in solution to furnish double conjugates.

Journal of Organic 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, COA of Formula: C39H35N5O8.

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