Tag: 100-200

Structure-Property Relationships in Click-Derived Donor-Triazole-Acceptor Materials was written by Kautny, Paul;Bader, Dorian;Stoeger, Berthold;Reider, Georg A.;Froehlich, Johannes;Lumpi, Daniel. And the article was included in Chemistry – A European Journal in 2016.Name: 2-Ethynylpyrimidine This article mentions the following:

To shed light on intramol. charge-transfer phenomena in 1,2,3-triazole-linked materials, a series of 1,2,3-triazole-linked push-pull chromophores were prepared and studied exptl. and computationally. Investigated modifications include variation of donor and/or acceptor strength and linker moiety as well as regioisomers. Photophys. characterization of intramol. charge-transfer features revealed ambipolar behavior of the triazole linker, depending on the substitution position. Furthermore, non-centrosym. materials were subjected to second-harmonic generation measurements, which revealed the high nonlinear optical activity of this class of materials. In the experiment, the researchers used many compounds, for example, 2-Ethynylpyrimidine (cas: 37972-24-0Name: 2-Ethynylpyrimidine).

2-Ethynylpyrimidine (cas: 37972-24-0) belongs to pyrimidine derivatives. Pyrimidines are isomeric with two other forms of diazines: pyridazine, with the nitrogen atoms in the 1 and 2 positions; and pyrazine, with the nitrogen atoms in the 1 and 4 positions. A Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones enables an efficient and facile synthesis of structurally important pyrimidines via a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization.Name: 2-Ethynylpyrimidine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Identification of potent and selective MTH1 inhibitors was written by Petrocchi, Alessia;Leo, Elisabetta;Reyna, Naphtali J.;Hamilton, Matthew M.;Shi, Xi;Parker, Connor A.;Mseeh, Faika;Bardenhagen, Jennifer P.;Leonard, Paul;Cross, Jason B.;Huang, Sha;Jiang, Yongying;Cardozo, Mario;Draetta, Giulio;Marszalek, Joseph R.;Toniatti, Carlo;Jones, Philip;Lewis, Richard T.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.COA of Formula: C5H6ClN3 This article mentions the following:

Structure based design of a novel class of aminopyrimidine MTH1 (MutT homolog 1) inhibitors is described. Optimization led to identification of I, a sub-nanomolar inhibitor of MTH1 with excellent cell permeability and good metabolic stability in microsomes. This compound robustly inhibited MTH1 activity in cells and proved to be an excellent tool for interrogation of the utility of MTH1 inhibition in the context of oncol. In the experiment, the researchers used many compounds, for example, 4-Chloro-5-methylpyrimidin-2-amine (cas: 20090-58-8COA of Formula: C5H6ClN3).

4-Chloro-5-methylpyrimidin-2-amine (cas: 20090-58-8) belongs to pyrimidine derivatives. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives. As nucleotides in DNA and RNA, pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.COA of Formula: C5H6ClN3

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthesis of new pyrimidine-4-carboxylic acid derivatives was written by Warczykowska, Iwona;Wojciechowski, Jan. And the article was included in Polish Journal of Chemistry in 1980.Formula: C5H2ClN3 This article mentions the following:

Aminolysis of 2-chloro-4-cyanopyridine (I) gave the nitriles II [R = cyano; R¹ = H, R² = 4-ClC₆H₄, 2-MeOC₆H₄, 4-Me₂NC₆H₄; R¹ = R² = Et; R¹R² = (CH₂CH₂)₂O] which were hydrolyzed with 5% aqueous NaOH to the acids II (R = CO₂H). Treatment of I with NaOMe-MeOH gave the ester III which was hydrolyzed to the acid with aqueous NaOH. In the experiment, the researchers used many compounds, for example, 2-Chloropyrimidine-4-carbonitrile (cas: 75833-38-4Formula: C5H2ClN3).

2-Chloropyrimidine-4-carbonitrile (cas: 75833-38-4) belongs to pyrimidine derivatives. The pyrimidine nitrogenous bases are derived from the organic compound pyrimidine through the addition of various functional groups. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.Formula: C5H2ClN3

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A novel synthesis of guanine PDE inhibitors via tricyclic imidazopyrimidines was written by Gala, Dinesh;DiBenedetto, Donald J.;Kugelman, Max;Mitchell, Michael B.. And the article was included in Tetrahedron Letters in 2003.HPLC of Formula: 54030-56-7 This article mentions the following:

A new method for the preparation of developmental tetracyclic guanine PDE inhibitors via a common tricyclic pyrimidine intermediate is described. Nitration of 6-amino-3-methyl-2-(methylthio)-4(3H)-Pyrimidinone gave 6-amino-3-methyl-2-(methylthio)-5-nitro-4(3H)-Pyrimidinone in 80% yield. Reaction of the latter with (1R,2R)-2-aminocyclopentanol gave rel-6-amino-2-[[(1R,2R)-2-hydroxycyclopentyl]amino]-3-methyl-5-nitro-4(3H)-pyrimidinone. Cyclization of the latter gave (5aR,8aS)-rel-4-amino-1,5a,6,7,8,8a-hexahydro-1-methyl-3-nitro-2H-cyclopent[4,5]imidazo[1,2-a]pyrimidin-2-one (I) as the key intermediate for rel-N-[(5aR,8aS)-4-amino-1,5a,6,7,8,8a-hexahydro-1-methyl-2-oxo-2H-cyclopent[4,5]imidazo[1,2-a]pyrimidin-3-yl]-4-(trifluoromethyl)benzamide (65% yield from I) and rel-N-[(5aR,8aS)-4-amino-1,5a,6,7,8,8a-hexahydro-1-methyl-2-oxo-2H-cyclopent[4,5]imidazo[1,2-a]pyrimidin-3-yl]heptanamide (81% yield from I). These compounds are intermediates for guanine PDE inhibitors (6aR,9aS)-rel-5,6a,7,8,9,9a-hexahydro-5-methyl-2-[[4-(trifluoromethyl)phenyl]methyl]cyclopent[4,5]imidazo[2,1-b]purin-4(1H)-one (Sch 51866) and (6aR,9aS)-rel-2-hexyl-5,6a,7,8,9,9a-hexahydro-5-methylcyclopent[4,5]imidazo[2,1-b]purin-4(1H)-one (Sch 59498). In the experiment, the researchers used many compounds, for example, 6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7HPLC of Formula: 54030-56-7).

6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7) belongs to pyrimidine derivatives. Heterocyclic compounds bearing the pyrimidine core are of tremendous interest as they constitute an important class of natural and synthetic compounds exhibiting diverse useful biological activities that hold attractive potential for clinical translation as therapeutic agents in alleviation of a myriad of diseases. As nucleotides in DNA and RNA, pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.HPLC of Formula: 54030-56-7

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Nonpeptidic inhibitors of human leukocyte elastase. 5. Design, synthesis, and x-ray crystallography of a series of orally active 5-aminopyrimidin-6-one-containing trifluoromethyl ketones was written by Veale, Chris A.;Bernstein, Peter R.;Bryant, Craig;Ceccarelli, Christopher;Damewood, James R. Jr.;Earley, Roger;Feeney, Scott W.;Gomes, Bruce;Kosmider, Ben J.. And the article was included in Journal of Medicinal Chemistry in 1995.Name: 5-Aminopyrimidin-4(3H)-one This article mentions the following:

The effects of changes in substitution in a series of 5-amino-2-pyrimidin-6-ones on both in vitro elastase-inhibitory activity and oral activity in an acute hemorrhagic assay were explored. These compounds contained either a trifluoromethyl ketone or a boronic acid moiety to bind covalently to the serine-195 OH group of human leukocyte elastase (HLE). Boronic acid-containing inhibitors were more potent than the corresponding trifluoromethyl ketones in vitro but were less active upon oral administration. One compound (I; R¹ = H; Ar = 4-fluorophenyl; R² = trifluoromethyl ketone) offered the best combination of oral potency, duration of action, and enzyme selectivity and, as such, was selected for further biol. testing. X-ray crystallog. of a cocrystd. complex of another compound (I; R¹ = CH₃SO₂; Ar = 4-aminophenyl; R² = trifluoromethyl ketone) and porcine pancreatic elastase demonstrated that the inhibitor is bound to the enzyme in a manner similar to that found previously for a closely related series of pyridone-containing inhibitors of HLE. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0Name: 5-Aminopyrimidin-4(3H)-one).

5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0) belongs to pyrimidine derivatives. Pyrimidine also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. A Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones enables an efficient and facile synthesis of structurally important pyrimidines via a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization.Name: 5-Aminopyrimidin-4(3H)-one

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Design, synthesis, and biological evaluation of novel 2′-methyl-2′-fluoro-6-methyl-7-alkynyl-7-deazapurine nucleoside analogs as anti-Zika virus agents was written by Yao, Guoqiang;Yu, Jianchen;Lin, Cai;Zhu, Yujia;Duan, Anna;Li, Mengfeng;Yuan, Jie;Zhang, Jiancun. And the article was included in European Journal of Medicinal Chemistry in 2022.HPLC of Formula: 37972-24-0 This article mentions the following:

Zika virus (ZIKV) is a mosquito-borne flavivirus and outbreaks of ZIKV have been reported in Africa, Americas and other parts of the world lately. The ZIKV epidemic has received extensive attention due to its ability to cause serious medical consequences and complications such as microcephaly and Guillain-Barre syndrome in recent years. Up to now, there are no specific treatments or vaccines available for ZIKV infection, which highlights the urgent need for developing new therapies. In this work, we designed and synthesized a series of novel 6-methyl-7-acetylenenyl-7-deazapurine nucleoside analogs as potential inhibitors of ZIKV replication. The biol. activities against ZIKV replication were evaluated and the structure-activity relationship (SAR) was also studied. Among the compounds evaluated, nucleoside analog 38 (EC50 = 2.8 ± 0.8 μM, EC90 = 6.8 ± 2.3 μM) showed the most potent anti-ZIKV activity with low cytotoxicity (CC50 = 54.1 ± 6.9 μM) in an A549 based cellular model. The inhibitory activity of 38 was about 5 times more potent than the pos. control NITD008. Notably, 38 showed similar inhibition potency against different ZIKV strains (ZG-01 and MR766) in a variety of host cell types including SNB19, A549, Huh7, Vero. In addition, 38 (Kd = 1.87 μM) has a stronger affinity to ZIKV RNA-dependent RNA polymerase (RdRp) protein than NITD008 (Kd = 3.43 μM) in the non-phosphorylation assay. These results indicated that compound 38 may serve as a promising candidate in future anti-ZIKV drug discovery. In the experiment, the researchers used many compounds, for example, 2-Ethynylpyrimidine (cas: 37972-24-0HPLC of Formula: 37972-24-0).

2-Ethynylpyrimidine (cas: 37972-24-0) belongs to pyrimidine derivatives. Pyrimidine also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. A Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones enables an efficient and facile synthesis of structurally important pyrimidines via a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization.HPLC of Formula: 37972-24-0

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

An Automated Continuous-Flow Platform for the Estimation of Multistep Reaction Kinetics was written by Reizman, Brandon J.;Jensen, Klavs F.. And the article was included in Organic Process Research & Development in 2012.HPLC of Formula: 62968-37-0 This article mentions the following:

Automated continuous flow systems coupled with online anal. and feedback have been previously demonstrated to model and optimize chem. syntheses with little a priori reaction information. However, these methods have yet to address the challenge of modeling and optimizing for product yield or selectivity in a multistep reaction network, where low selectivity toward desired product formation can be encountered. Here we demonstrate an automated system capable of rapidly estimating accurate kinetic parameters for a given reaction network using maximum likelihood estimation and a D-optimal design of experiments The network studied is the series-parallel nucleophilic aromatic substitution of morpholine onto 2,4-dichloropyrimidine. To improve the precision of the estimated parameters, we demonstrate the use of the automated platform first in optimization of the yield of the less kinetically favorable 2-substituted product. Then, upon isolation of the intermediates, we use the automated system with maximum a posteriori estimation to minimize uncertainties in the network parameters. From considering the steps of the reaction network in isolation, the kinetic parameter uncertainties are reduced by 50%, with less than 5 g of the dichloropyrimidine substrate consumed over all experiments We conclude that isolating pathways in the multistep reaction network is important to minimizing uncertainty for low sensitivity rate parameters. In the experiment, the researchers used many compounds, for example, 4-(2-Chloropyrimidin-4-yl)morpholine (cas: 62968-37-0HPLC of Formula: 62968-37-0).

4-(2-Chloropyrimidin-4-yl)morpholine (cas: 62968-37-0) belongs to pyrimidine derivatives. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own.HPLC of Formula: 62968-37-0

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthesis of functionalized arylpyridines and -pyrimidines by domino [4+2]/retro [4+2] cycloadditions of electron-rich dienes with alkynylpyridines and -pyrimidines was written by Abid, Obaid-ur-Rahman;Nawaz, Muhammad;Ibad, Muhammad Farooq;Khera, Rasheed Ahmad;Iaroshenko, Viktor;Langer, Peter. And the article was included in Organic & Biomolecular Chemistry in 2011.Related Products of 37972-24-0 This article mentions the following:

Aryl-substituted pyridines and pyrimidines were prepared by [4 + 2] cycloadditions of alkynyl-substituted pyridines and pyrimidines with electron-rich dienes. The reactions proceed by formation of a bridged cycloadduct and subsequent thermal extrusion of ethylene. The pyridine moiety plays a crucial role for the success of the reaction. In the experiment, the researchers used many compounds, for example, 2-Ethynylpyrimidine (cas: 37972-24-0Related Products of 37972-24-0).

2-Ethynylpyrimidine (cas: 37972-24-0) belongs to pyrimidine derivatives. The aromatic compound pyrimidine, and its derivatives, are ubiquitous in nature. They are found in nucleic acids, vitamins, amino acids, antibiotics, alkaloids, and a variety of toxins. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own.Related Products of 37972-24-0

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Syntheses of pyrimidines and thiazolo[5,4-d]pyrimidines was written by Marchal, L.;Promel, R.;Martin, R. H.;Cardon, A.. And the article was included in Bulletin des Societes Chimiques Belges in 1960.Recommanded Product: 69785-94-0 This article mentions the following:

A series of thiazolo[5,4-d]pyrimidines substituted in the 7 position were prepared from 7-chlorothiazolo[5,4-d]pyrimidine (I). Preliminary to the synthesis of I, 5-amino-4,6-dihydroxypyrimidine (II) was prepared by the method of Hull (cf. CA 46, 987d) in increased yield (78% instead of 40%) by effecting condensation in the presence of 3 equivalents of NaOEt. To 1 g. 5-amino-4,6-dichloropyrimidine (III) prepared from II by the known route (cf. CA 49, 10308f) and dissolved in 20 ml. MeOH was added 0.805 g. NaSH in 10 ml. MeOH and the mixture refluxed 0.5 hr. The product, 5-amino-4-chloro-6-mercaptopyrimidine (IV), decomposing 190-220°, 88% yield, was characterized by methylation in alk. solution with MeI to give 5-amino-4-chloro-6-methylthiopyrimidine (V), m. 94.5-96° after sublimation at 80°/0.2 mm. Reaction of thiourea instead of NaSH with III led not to IV but to the disubstituted product 5-amino-4,6-dimercaptopyrimidine, m. above 330°. Heating 2 g. of IV in 28 ml. HC(OEt)₃ at reflux gave 81% I, m. 152-4° (corrected) after sublimation at 110°/0.1 mm. From I was prepared a series of 7-X-substituted-thiazolo[5,4-d]pyrimidines (X, m.p., and % yield given): furfurylamino, 93.5-95°, 65; benzylamino, 129-30°, 59%; hydrazino, decompose 200-60°, 71; methoxy, 164-6°, 90.5; hydroxy, above 300°, 83; mercapto, 330°, 94.5. Attempted preparation of 7-aminothiazolo[5,4-d]pyrimidine by reaction of I with ammonia in aqueous or alc. solution gave an unidentified product. Also, dehalogenation of I using Pd-C or Raney Ni failed to give thiazolo[5,4-d]pyrimidine (VI). As the first step in another route to synthesize VI, desulfurization of V with Raney Ni gave not the expected product but 5-aminopyrimidine (VII). Desulfurization of 0.5 g. IV by heating an aqueous ammoniacal solution with 3 g. Raney Ni 15 min. gave a mixture of VII, m. 166-9°, and 5-amino-4-chloropyrimidine, decomposing 110° after sublimation (VIII), separated by chromatography on alumina. IV (1 g.) in 20 ml. MeOH was added to a stirred solution of NaOMe (from 0.14 g. of Na in 3.5 ml. of MeOH) at room temperature Stirring was continued 12 hrs. On workup was obtained 95% 5-amino-4-chloro-6-methoxypyrimidine (IX), m. 79-80° after sublimation at 60°/0.005 mm. Dehalogenation of 0.49 g. IX in 0.43 ml. Et₃N and 20 ml. MeOH with 0.3 g. of 5% Pd-C at ambient temperature gave 83% 5-amino-4-methoxypyrimidine (X), m. 61-3° (corrected). Hydrolysis of X with concentrated HCl at reflux temperature for 0.5 hr. gave 70% 5-amino-4-hydroxypyrimidine (XI), m. 206-8° after sublimation. Attempted transformation of XI to VIII with POCl₃ was unsuccessful. 4-Chloro-6-mercaptopyrimidine (0.48 g.), prepared by reaction of 1 g. 4,6-dichloropyrimidine with 0.37 g. NaSH in 5 ml. of MeOH at room temperature 15 hrs., was treated with MeI in basic solution to give 36% 4-chloro-6-methylthiopyrimidine, m. 50-1° after sublimation. I and 7-furfurylaminothiazolo[5,4-d]pyrimidine were inactive against five exptl. tumors. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0Recommanded Product: 69785-94-0).

5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0) belongs to pyrimidine derivatives. Heterocyclic compounds bearing the pyrimidine core are of tremendous interest as they constitute an important class of natural and synthetic compounds exhibiting diverse useful biological activities that hold attractive potential for clinical translation as therapeutic agents in alleviation of a myriad of diseases. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.Recommanded Product: 69785-94-0

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Unprecedented Allenylidene Transfer from Chromium to Tungsten was written by Szesni, Normen;Drexler, Matthias;Fischer, Helmut. And the article was included in Organometallics in 2006.Quality Control of 2-Ethynylpyrimidine This article mentions the following:

Pyrimidylallenylidene complexes 1 ([(CO)₅M:C:C:C(NC₃H₃NEt)]; M = Cr (a), W (b)) were prepared in a 1-pot procedure from readily available 2-ethynylpyrimidine, BuLi, [(CO)₅M(THF)], and triethyloxonium tetrafluoroborate. In addition to 1a,b, the homobinuclear allenylidene complexes 2a,b ([(CO)₅M:C:C:C(NC₃H₃NEt)M(CO)₅]; M = Cr, W) were formed. In 2a,b the 2nd (CO)₅M moiety is attached to the non-alkylated N atom of the pyrimidyl ring. Treatment of the Cr complex 1a with an excess of [(CO)₅W(THF)] afforded the W allenylidene complex 2b by transmetalation of the allenylidene ligand and addition of (CO)₅W. The allenylidene ligands of other Cr allenylidene complexes [(CO)₅Cr:C:C:C(R¹)R²] could likewise be transferred to W. In contrast, the reverse transmetalation from W to Cr could not be achieved. DFT calculations indicate that the reaction proceeds by an associative rather than a dissociative pathway. The initiating reaction step is coordination of a (CO)₅W fragment to the C_α-C_β bond of the allenylidene ligand. In the experiment, the researchers used many compounds, for example, 2-Ethynylpyrimidine (cas: 37972-24-0Quality Control of 2-Ethynylpyrimidine).

2-Ethynylpyrimidine (cas: 37972-24-0) belongs to pyrimidine derivatives. The aromatic compound pyrimidine, and its derivatives, are ubiquitous in nature. They are found in nucleic acids, vitamins, amino acids, antibiotics, alkaloids, and a variety of toxins. Pyrimidine derivatives have been used in a wide variety of pharmaceuticals including general anesthetics, anti-epilepsy medication, anti-malaria medication, drugs for treating high blood pressure, and HIV medication.Quality Control of 2-Ethynylpyrimidine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia