Tag: 100-200

Reactivity of 6-aminopyrimidin-4-(3H)-ones towards dimethyl acetylenedicarboxylate (DMAD). Tandem Diels-Alder/retro Diels-Alder (DA/RDA) reaction in the synthesis of 2-aminopyridines was written by Cobo, Justo;Garcia, Celeste;Melguizo, Manuel;Sanchez, Adolfo;Nogueras, Manuel. And the article was included in Tetrahedron in 1994.Reference of 54030-56-7 This article mentions the following:

The reactions of 6-aminopyrimidin-4-(3H)-one derivatives I (R = H, Me; X = O, S) with DMAD were studied. 2-Aminopyridines and 6-amino-5-vinylpyrimidin-4-(3H)-ones were obtained as main products, which can be explained on the basis of DA/RDA reactions, or Michael addition on pyrimidine derivatives In the experiment, the researchers used many compounds, for example, 6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7Reference of 54030-56-7).

6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7) belongs to pyrimidine derivatives. The pyrimidine nitrogenous bases are derived from the organic compound pyrimidine through the addition of various functional groups. For example, the neurotoxin tetrodotoxin is a pyrimidine derivative. It is found in a number of species including the Japanese puffer fish, the blue-ringed octopus, and the orange-bellied newt. Tetrodotoxin prevents the transmission of nerve signals and can result in paralysis and death.Reference of 54030-56-7

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

SAR Optimization studies on a novel series of 2-anilinopyrimidines as selective inhibitors against triple-negative breast cancer cell line MDA-MB-468 was written by Jo, Jeyun;Kim, Heegyu;Oh, Ji Youn;Kim, Soyeong;Park, Yeong Hye;Choi, Hyeonjin;Jeong, Jee-Yeong;Jung, Young-Suk;Yun, Hwayoung. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.SDS of cas: 62968-37-0 This article mentions the following:

Two series of 2-anilinopyrimidines I [R¹ = pyrrol-1-yl, indol-1-yl, 4-Me-piperidin-1-yl; R² = NMe₂, morpholin-4-yl, thiomorpholin-4-yl, piperidin-1-yl] and II [R³ = methoxy, cyclohexyl; R⁴ = indol-1-yl, pyrrolidin-1-yl, 4-Cl-piperidin-1-yl, etc.] as a selective inhibitors of the basal-like TNBC cell line MDA-MB-468 were reported. An extensive anal. of structure-activity relationships of the analogs I and II revealed that aminoalkyl groups at the end of the Pr chain are amenable to modification. Compound II [R³ = cyclohexyl; R⁴ = 4-Cl-piperidin-1-yl] was found to be the most potent and selective and was about three times more potent and selective than I [R¹ = 4-Me-piperidin-1-yl; R² = piperidin-1-yl] was against the TNBC cells. In the experiment, the researchers used many compounds, for example, 4-(2-Chloropyrimidin-4-yl)morpholine (cas: 62968-37-0SDS of cas: 62968-37-0).

4-(2-Chloropyrimidin-4-yl)morpholine (cas: 62968-37-0) belongs to pyrimidine derivatives. The pyrimidine nitrogenous bases are derived from the organic compound pyrimidine through the addition of various functional groups. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.SDS of cas: 62968-37-0

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Imidazopyridazine Hepatitis C Virus Polymerase Inhibitors. Structure-Activity Relationship Studies and the Discovery of a Novel, Traceless Prodrug Mechanism was written by Leivers, Martin;Miller, John F.;Chan, Stephanie A.;Lauchli, Ryan;Liehr, Sebastian;Mo, Wenyan;Ton, Tony;Turner, Elizabeth M.;Youngman, Michael;Falls, J. Greg;Long, Susan;Mathis, Amanda;Walker, Jill. And the article was included in Journal of Medicinal Chemistry in 2014.Synthetic Route of C6H6N2O2 This article mentions the following:

By reducing the basicity of the core heterocycle in a series of HCV NS5B inhibitors, the hERG liability was reduced. The SAR was then systematically explored to increase solubility and enable dose escalation while retaining potency. During this exploration, a facile decarboxylation was noted and was exploited as a novel prodrug mechanism. The synthesis and characterization of these prodrugs and their utilization in chronic toxicity studies are presented. In the experiment, the researchers used many compounds, for example, 2-Methoxypyrimidine-5-carbaldehyde (cas: 90905-32-1Synthetic Route of C6H6N2O2).

2-Methoxypyrimidine-5-carbaldehyde (cas: 90905-32-1) belongs to pyrimidine derivatives. Pyrimidine also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. 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.Synthetic Route of C6H6N2O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Central nervous system inhibiting agents, V. Conversion of dicyanodiamide to the 5,6,7,8-tetrahydroquinazoline system was written by Kreutzberger, Alfred;Sellheim, Michael. And the article was included in Chemiker-Zeitung in 1984.Related Products of 1193-74-4 This article mentions the following:

Condensation of NCNHC(:NH)NH₂ with 2-acetylcyclohexanone gave cyanamionquinazoline I which was immediately hydrolyzed to ureidoquinazoline II. The structure of II was confirmed by IR, ¹H NMR, ¹H broad-band decoupled ¹³C NMR, and GATED spectra. In the experiment, the researchers used many compounds, for example, 4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4Related Products of 1193-74-4).

4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4) 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. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.Related Products of 1193-74-4

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Design, Synthesis, Anti-Tomato Spotted Wilt Virus Activity, and Mechanism of Action of Thienopyrimidine-Containing Dithioacetal Derivatives was written by Wang, Yanju;Luo, Yuqin;Hu, Deyu;Song, Baoan. And the article was included in Journal of Agricultural and Food Chemistry in 2022.Recommanded Product: 4-Chloro-7-methylthieno[3,2-d]pyrimidine This article mentions the following:

Currently, there is insufficient virucide to effectively control tomato spotted wilt virus (TSWV). To address this pending issue, a series of thienopyrimidine-containing dithioacetal derivatives were prepared and tested for their anti-TSWV activities. A subsequent three-dimensional quant. structure-activity relationship was constructed to indicate the development of optimal compound I. The obtained compound I had excellent anti-TSWV curative, protective, and inactivating activities (63.0, 56.6, and 74.1%, resp.), and the EC₅₀ values of protective and inactivating activities of compound 35 were 252.8 and 113.5 mg/L, resp., better than those of ningnanmycin (284.8 and 144.7 mg/L) and xiangcaoliusuobingmi (624.9 and 300.0 mg/L). In addition, the anti-TSWV activity of compound I was associated with defense-related enzyme activities, enhanced photosynthesis, and reduced stress response, thereby enhancing disease resistance. In the experiment, the researchers used many compounds, for example, 4-Chloro-7-methylthieno[3,2-d]pyrimidine (cas: 175137-21-0Recommanded Product: 4-Chloro-7-methylthieno[3,2-d]pyrimidine).

4-Chloro-7-methylthieno[3,2-d]pyrimidine (cas: 175137-21-0) belongs to pyrimidine derivatives. The pyrimidine derivatives can easily interact with enzymes, genetic materials, and bio components within the cell. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own.Recommanded Product: 4-Chloro-7-methylthieno[3,2-d]pyrimidine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Pyrimidines. V. Synthesis of 5-amino-4-hydroxypyrimidine, a new isomer of cytosine was written by Boarland, M. P. V.;McOmie, J. F. W.. And the article was included in Journal of the Chemical Society in 1952.COA of Formula: C4H5N3O This article mentions the following:

Treatment of 30 g. NaOCH:C(NHBz)CO₂Et in 60 cc. H₂O 2 days at 37° with 15.2 g. methylthiuronium sulfate and 6.2 g. KOH in 80 cc. H₂O and acidification with HOAc precipitated 91% 5-benzamido-4-hydroxy-2-(methylthio)pyrimidine (I), m. 268° (from aqueous dioxane). I (3.0 g.), refluxed 1 hr. with 30 cc. Ac₂O, was converted to 1.2 g. 5-acetamido-4-hydroxy-2-(methylthio)pyrimidine, m. 220-1° (decomposition), absorption maximum in 0.1N NaOH at 256 and 291 mμ (log ε 4.09 and 4.10); after sublimation to remove BzOH and recrystallization from EtOH it m. 236°. Refluxing 10.0 g. I in 300 cc. aqueous dioxane 3.5 hrs. with 40 g. Raney Ni gave 4.7 g. 5-benzamido-4-hydroxypyrimidine, m. 245-6° (from aqueous EtOH). POCl₃ (50 cc.) and 9.0 g. I, heated 3 hrs., gave 77% 2′-methylthio-2-phenylpyrimidino(5′,4′:4,5)oxazole (II), m. 155-6° (from EtOH). 2-Phenylpyrimidino(5′,4′:4,5)oxazole (62%), m. 114° after recrystallization from aqueous EtOH and sublimation at 110° and 0.1 mm., resulted from refluxing 2.0 g. II in 150 cc. EtOH 3 hrs. with 8 g. Raney Ni. HCO₂Et (14 cc.), 20 g. EtO₂CNHCH₂CO₂Et, and 2.8 g. Na in 150 cc. C₆H₆, heated 0.75 hr. and let stand, precipitated on addition of Et₂O 22.5 g. NaOCH:C(NHCO₂Et)CO₂Et (III). Treatment of 37.3 g. III in 50 cc. H₂O with 28 g. ethylthiuronium bromide and 8.5 g. KOH in 50 cc. H₂O 15 hrs. gave on acidification IV, m. 200-56° (decomposition), which, on crystallization from aqueous EtOH and paper chromatography with EtOAc-H₂O-HOAc (3:2:1), indicated a mixture of 2-ethylthio-5-formamido-4-hydroxypyrimidine (V) (R_f 0.90) and 5-(ethoxycarbonyl)amino-2-ethylthio-4-hydroxypyrimidine (VI) (R_f 0.96). 5-Amino-2-ethylthio-4-hydroxypyrimidine (VII), m. 159° (from H₂O), absorption maximum in 0.1N NaOH 263 and 295 mμ (log ε 3.99 and 3.92), was obtained by refluxing IV with aqueous NaOH. VII (0.4 g.), refluxed with 10 cc. HCO₂C₅H₁₁, gave 0.35 g. V, m. 269-70 (from 50% EtOH), absorption maximum in 0.1N NaOH at 259 and 296 mμ (log ε 4.02 and 4.05). VI, m. 190-1°, absorption maximum in 0.1N NaOH at 255 and 291 mμ (log ε 3.99 and 3.99), was obtained from 1 g. IV by solution in 20 cc. Ac₂O, dilution with H₂O, and recrystallization from HOAc, and in 90% yield by treatment of 0.5 g. VII with 0.13 g. Na₂CO₃ in 20 cc. H₂O and 0.25 cc. ClCO₂Et. Desulfurization of 2.0 g. VII 3 hrs. with 8 g. Raney Ni in 70 cc. H₂O gave 0.8 g. 5-amino-4-hydroxypyrimidine (VIII), m. 211-12° (from EtOH), absorption maximum in 0.1N HCl at 290 mμ (log ε 4.14) and in 0.1N NaOH at 248 and 282 mμ (log ε 3.88 and 3.87). VIII and VII in 1% solution showed no activity against Staphylococcus aureus by the agar-cup diffusion method. In the experiment, the researchers used many compounds, for example, 5-Aminopyrimidin-4(3H)-one (cas: 69785-94-0COA of Formula: C4H5N3O).

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. 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: C4H5N3O

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Design, Synthesis, and Biological Evaluation of 16-Substituted 4-Azasteroids as Tissue-Selective Androgen Receptor Modulators (SARMs) was written by Mitchell, Helen J.;Dankulich, William P.;Hartman, George D.;Prueksaritanont, Thomayant;Schmidt, Azriel;Vogel, Robert L.;Bai, Chang;McElwee-Witmer, Sheila;Zhang, Hai Z.;Chen, Fang;Leu, Chih-Tai;Kimmel, Donald B.;Ray, William J.;Nantermet, Pascale;Gentile, Michael A.;Duggan, Mark E.;Meissner, Robert S.. And the article was included in Journal of Medicinal Chemistry in 2009.Electric Literature of C6H6N2O2 This article mentions the following:

A novel series of 16-substituted-4-azasteroids has been prepared as potential tissue-selective androgen receptor modulators. These ligands display potent hAR binding and agonist activity, low virilizing potential, and good pharmacokinetic profiles in dogs. On the basis of its in vitro profile, I was evaluated in the OVX and ORX rat models and exhibited an osteoanabolic, tissue-selective profile. In the experiment, the researchers used many compounds, for example, 2-Methoxypyrimidine-5-carbaldehyde (cas: 90905-32-1Electric Literature of C6H6N2O2).

2-Methoxypyrimidine-5-carbaldehyde (cas: 90905-32-1) belongs to pyrimidine derivatives. Pyrimidine also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. 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.Electric Literature of C6H6N2O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A facile and rapid preparation of hydroxamic acids by hydroxylaminolysis using DBU as base was written by Beillard, Audrey;Bhurruth-Alcor, Yushma;Bouix-Peter, Claire;Bouquet, Karinne;Chambon, Sandrine;Clary, Laurence;Harris, Craig S.;Millois, Corrine;Mouis, Gregoire;Ouvry, Gilles;Pierre, Romain;Reitz, Arnaud;Tomas, Loic. And the article was included in Tetrahedron Letters in 2016.Computed Properties of C5H3ClN2O2 This article mentions the following:

While there are many protocols for the preparation of hydroxamic acids from their corresponding carboxylic acid or carboxylic ester precursors, most use strong mineral bases that can lead to carboxylic acid impurities that can be difficult to remove using standard chromatog. techniques. This problem is exacerbated when the carbonyl group is hindered. Herein, we communicate a robust hydroxylaminolysis protocol for the preparation of hydroxamic acids in high yield and purity. In the experiment, the researchers used many compounds, for example, 5-Chloropyrimidine-2-carboxylic acid (cas: 38275-61-5Computed Properties of C5H3ClN2O2).

5-Chloropyrimidine-2-carboxylic acid (cas: 38275-61-5) belongs to pyrimidine derivatives. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. 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.Computed Properties of C5H3ClN2O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthesis of the caffeine metabolites 5-acetylamino-6-formylamino-3-methyluracil (AFMU) and 5-acetylamino-6-amino-3-methyluracil (AAMU) on a preparative scale was written by Roehrkasten, R.;Raatz, P.;Kreher, R. P.;Blaszkewicz, M.. And the article was included in Zeitschrift fuer Naturforschung, B: Chemical Sciences in 1997.Related Products of 54030-56-7 This article mentions the following:

6-Amino- and 6-formylamino-5-acetylamino-3-methyluracil were prepared as standards for qual. and quant. anal. in connection with caffeine metabolism in 6 resp. 7 steps starting from thiourea and NCCH₂CO₂Et. In the experiment, the researchers used many compounds, for example, 6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7Related Products of 54030-56-7).

6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7) belongs to pyrimidine derivatives. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.Related Products of 54030-56-7

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Design and synthesis of 1,2,3-triazole incorporated pyrimidine-benzoxazole derivatives as anticancer agents was written by Sudhakar, D. G. S.;Rao, A. Srinivasa;Reddy, Ch. Venkata Ramana;Somaiah, Nalla. And the article was included in Chemical Data Collections in 2022.COA of Formula: C6H4N2 This article mentions the following:

A new library of 1,2,3-triazole linked pyrimidine-benzoxazole derivatives I [Ar = pyridin-4-yl, 4-ClC₆H₄, pyrimidin-2-yl, etc.] was synthesized and characterized. Further, the preliminary anticancer activities of compounds I were tested on four human cancer cell lines such as prostate cancer (PC3 and DU-145), lung cancer (A549) and breast cancer (MCF-7) by using of MTT method. These activities were compared with clin. drug candidate etoposide. Among the screened compounds, five compounds I [R = pyridin-4-yl, pyrimidin-2-yl, 3,5-(Me)₂C₆H₃, 3,5-(OMe)₂C₆H₃, 3,4,5-(OMe)₃C₆H₂] exhibited considerable activities on four cell lines. In which one compound I [R = pyrimidin-2-yl] showed most promising activity among the synthesized compounds In the experiment, the researchers used many compounds, for example, 2-Ethynylpyrimidine (cas: 37972-24-0COA of Formula: C6H4N2).

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. For example, the neurotoxin tetrodotoxin is a pyrimidine derivative. It is found in a number of species including the Japanese puffer fish, the blue-ringed octopus, and the orange-bellied newt. Tetrodotoxin prevents the transmission of nerve signals and can result in paralysis and death.COA of Formula: C6H4N2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia