Category: pyrimidines

In 1978,Tetrahedron Letters included an article by Lapachev, V. V.; Zagulyaeva, O. A.; Bichkov, S. F.; Mamaev, V. P.. Formula: C9H9N3O2. The article was titled 《Tautomerism in the pyrimidylmethane systems》. The information in the text is summarized as follows:

The tautomerism of pyrimidyl-4-methanes I [R = CH(CN)CO2Et, R1 = Me, CF3; R = CH2NO2, R1 = Me, H] was studied by 13C and 1H NMR methods. In the presence of DMSO pyrimidine, ortho quinoid and para quinoid forms were observed; the tautomeric equilibrium between these forms, especially between pyrimidylidene tautomers, depends strongly on solvent and is more complicated than suggested by H. Feuer and J. P. Lawrence (1972). Pyrimidine-pyrimidylidene equilibrium were also observed in the pyrimidyl-2-methanes II (R = H, R1 = H, Me, Br, Cl, OMe, NMe2; R = Me, Ph, OMe, R1 = H).Ethyl 2-cyano-2-(pyrimidin-2-yl)acetate(cas: 65364-63-8Formula: C9H9N3O2) was used in this study.

Ethyl 2-cyano-2-(pyrimidin-2-yl)acetate(cas: 65364-63-8) is a member of pyrimidine. Pyrimidine derivatives are an important class of N-heterocycles. They are well-known for their wide spectrum of promising biological activities such as antitumors, bactericidals, and fungicidal.Formula: C9H9N3O2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Chen, Bang-Chi; Quinlan, Sandra L.; Reid, J. Gregory; Spector, Richard H. published an article on February 19 ,1998. The article was titled 《A new thymine free synthesis of the anti-AIDS drug d4T via regio/stereo controlled β-elimination of bromoacetates》, and you may find the article in Tetrahedron Letters.Formula: C17H16N2O5 The information in the text is summarized as follows:

The anti-AIDS drug d4T was prepared without contamination of the nucleoside bond cleaved byproduct thymine from the readily available ribonucleoside 5-methyluridine. This was accomplished by using a new strategy which involved a regio/stereo controlled β-elimination of trans-bromoacetates. The experimental process involved the reaction of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Formula: C17H16N2O5)

((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Formula: C17H16N2O5

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Recommanded Product: ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoateOn October 30, 1995 ,《5′-Benzoyl-2’α-bromo-3′-O-methanesulfonylthymidine: a superior nucleoside for the synthesis of the anti-AIDS drug D4T (stavudine)》 was published in Tetrahedron Letters. The article was written by Chen, Bang-Chi; Quinlan, Sandra L.; Stark, Derron R.; Reid, J. Gregory; Audia, Vicki H.; George, Jacqueline G.; Eisenreich, Emerich; Brundidge, Steve P.; Racha, Saibaba; Spector, Richard H.. The article contains the following contents:

The anti-AIDS drug d4T is prepared in 75% overall yield starting from the readily available ribonucleoside 5-methyluridine. The key step in this new synthesis is the zinc-induced reductive elimination of the bromomesylate I, which affords d4T without nucleoside bond cleavage. A facile procedure for the deprotection/isolation of this highly water soluble product is also described. After reading the article, we found that the author used ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Recommanded Product: ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate)

((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Recommanded Product: ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

《Green oxidant H2O2 as a hydrogen atom transfer reagent for visible light-mediated Minisci reaction》 was published in New Journal of Chemistry in 2019. These research results belong to Zhao, Hong; Li, Zhenlong; Jin, Jian. HPLC of Formula: 14001-60-6 The article mentions the following:

A visible light-mediated “”green”” protocol for metal-free oxidative coupling of heteroarenes and aliphatic C-H components were achieved via a radical pathway. This cross-dehydrogenative coupling method features a broad scope of substrates. The green oxidant H2O2 was used as a hydrogen atom transfer reagent, which was environmentally benign, low cost, and atom economical. In the part of experimental materials, we found many familiar compounds, such as 2-Methoxy-4-methylpyrimidine(cas: 14001-60-6HPLC of Formula: 14001-60-6)

2-Methoxy-4-methylpyrimidine(cas: 14001-60-6) is a member of ether. When aromatic ethers are exposed to halogen in the presence or absence of a catalyst, they undergo halogenation, such as bromination.HPLC of Formula: 14001-60-6

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Manzoor, Shoaib; Gabr, Moustafa T.; Rasool, Bisma; Pal, Kavita; Hoda, Nasimul published their research in Bioorganic Chemistry in 2021. The article was titled 《Dual targeting of acetylcholinesterase and tau aggregation: Design, synthesis and evaluation of multifunctional deoxyvasicinone analogues for Alzheimer′s disease》.Safety of 2,4-Dichloropyrimidine The article contains the following contents:

Development of multitargeted ligands have demonstrated remarkable efficiency as potential therapeutics for Alzheimer′s disease (AD). Herein, we reported a new series of deoxyvasicinone analogs as dual inhibitor of acetylcholinesterase (AChE) and tau aggregation that function as multitargeted ligands for AD. All the multitargeted ligands 11(a-j) and 15(a-g) were designed, synthesized, and validated by 1HNMR, 13CNMR and mass spectrometry. All the synthesized compounds 11(a-j) and 15(a-g) were screened for their ability to inhibit AChE, BACE1, amyloid fibrillation, α-syn aggregation, and tau aggregation. All the screened compounds possessed weak inhibition of BACE-1, Aβ42 and α-syn aggregation. However, several compounds were identified as potential hits in the AChE inhibitory screening assay and cellular tau aggregation screening. Among all compounds, 11f remarkably inhibited AChE activity and cellular tau oligomerization at single-dose screening (10 μM). Moreover, 11f displayed a half-maximal inhibitory concentration (IC50) value of 0.91 ± 0.05 μM and half-maximal effective concentration (EC50) value of 3.83 ± 0.51 μM for the inhibition of AChE and cellular tau oligomerization, resp. In addition, the neuroprotective effect of 11f was determined in tau-expressing SH-SY5Y cells incubated with Aβ oligomers. These findings highlighted the potential of 11f to function as a multifunctional ligand for the development of promising anti-AD drugs. The results came from multiple reactions, including the reaction of 2,4-Dichloropyrimidine(cas: 3934-20-1Safety of 2,4-Dichloropyrimidine)

2,4-Dichloropyrimidine(cas: 3934-20-1) is a member of organic chlorides. Almost all organochlorine compounds are synthesized. It is widely used as intermediates, solvents and pesticides of chemical synthetic products.Safety of 2,4-Dichloropyrimidine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

《Europium-Doped Nanoparticles for Cellular Luminescence Lifetime Imaging via Multiple Manipulations of Aggregation State》 was written by Fang, Fang; Zhao, Dongxu; Zhang, Yinfeng; Li, Min; Ye, Jun; Zhang, Jinfeng. Computed Properties of C4H2Cl2N2 And the article was included in ACS Applied Bio Materials in 2020. The article conveys some information:

Luminescence lifetime imaging (LLIM) holds great promise in biomedical research owing to its excellent sensitivity and remarkable temporal-spatial resolution, but the development of effective long-lived luminescent probes for LLIM remains an unmet need. Herein, we designed two water-dispersible europium-doped nanoparticles (Eu-D1 and Eu-D2 NPs) for cellular LLIM, showing intense red luminescence emission and an increased lifetime of 4 orders of magnitude (~56 000 times) than undoped NPs, which could be attributed to the multiple manipulations of their aggregation states, including efficient Förster resonance energy transfer (FRET), suppressed self-quenching, and restrained solvent effects. With good bioavailability, the as-developed NPs were demonstrated as reliable candidates for long-lifetime imaging agents. Such a simple and versatile strategy could be extended to develop various luminescent nanoprobes for advanced high-precision bioimaging. After reading the article, we found that the author used 4,6-Dichloropyrimidine(cas: 1193-21-1Computed Properties of C4H2Cl2N2)

4,6-Dichloropyrimidine(cas: 1193-21-1) is a member of organic chlorides. Organic chloride content in crude oil can be detected through specialized laboratory analysis. Care and attention are essential while sampling and testing.Computed Properties of C4H2Cl2N2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 2019,Biochemistry included an article by Kalvaitis, Mindaugas E.; Johnson, Luke A.; Mart, Robert J.; Rizkallah, Pierre; Allemann, Rudolf K.. Reference of 2,4,6-Trichloropyrimidine. The article was titled 《A Noncanonical Chromophore Reveals Structural Rearrangements of the Light-Oxygen-Voltage Domain upon Photoactivation》. The information in the text is summarized as follows:

Light-oxygen-voltage (LOV) domains are increasingly used to engineer photoresponsive biol. systems. While the photochem. cycle is well documented, the allosteric mechanism by which formation of a cysteinyl-flavin adduct leads to activation is unclear. Via replacement of FMN with 5-deazaflavin mononucleotide (5dFMN) in the Aureochrome1a (Au1a) transcription factor from Ochromonas danica, a thermally stable cysteinyl-5dFMN adduct was generated. High-resolution crystal structures (<2 Å) under different illumination conditions with either FMN or 5dFMN chromophores reveal three conformations of the highly conserved glutamine 293. An allosteric hydrogen bond network linking the chromophore via Gln293 to the auxiliary A'α helix is observed With FMN, a ""flip"" of the Gln293 side chain occurs between dark and lit states. 5DFMN cannot hydrogen bond through the C5 position and proved to be unable to support Au1a domain dimerization. Under blue light, the Gln293 side chain instead ""swings"" away in a conformation distal to the chromophore and not previously observed in existing LOV domain structures. Together, the multiple side chain conformations of Gln293 and functional anal. of 5dFMN provide new insight into the structural requirements for LOV domain activation.2,4,6-Trichloropyrimidine(cas: 3764-01-0Reference of 2,4,6-Trichloropyrimidine) was used in this study.

2,4,6-Trichloropyrimidine(cas: 3764-01-0) is a member of organic chlorides. Almost all organochlorine compounds are synthesized. It is widely used as intermediates, solvents and pesticides of chemical synthetic products.Reference of 2,4,6-Trichloropyrimidine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 2008,Seela, Frank; Xu, Kuiying published 《7-halogenated 7-deazapurine 2′-deoxyribonucleosides related to 2′-deoxyadenosine, 2′-deoxyxanthosine, and 2′-deoxyisoguanosine: syntheses and properties》.Helvetica Chimica Acta published the findings.Reference of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine The information in the text is summarized as follows:

A series of 7-fluorinated 7-deazapurine 2′-deoxyribonucleosides related to 2′-deoxyadenosine, 2′-deoxyxanthosine, and 2′-deoxyisoguanosine as well as intermediates, e.g. I, were synthesized. The 7-fluoro substituent was introduced in 2,6-dichloro-7-deaza-9H-purine with Selectfluor. Apart from 2,6-dichloro-7-fluoro-7-deaza-9H-purine, the 7-chloro compound was formed and used for the glycosylation reaction; the separation of the 7-fluoro from the 7-chloro compound was performed on the level of the unprotected nucleosides. Other halogen substituents were introduced with N-halogenosuccinimides. The 2′-deoxyisoguanosine derivative I was prepared from 2-chloro-7-fluoro-7-deaza-2′-deoxyadenosine via a photochem. induced nucleophilic displacement reaction. The pKa values of the halogenated nucleosides were determined 13C-NMR chem.-shift dependencies of C(7), C(5), and C(8) were related to the electronegativity of the 7-halogen substituents. In aqueous solution, 7-halogenated 2′-deoxyribonucleosides show an approx. 70% S population. In the experiment, the researchers used 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(cas: 90213-66-4Reference of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine)

2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(cas: 90213-66-4) belongs to pyrimidine. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own. Reference of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidineThey 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.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Xie, Ting; Lim, Sang Min; Westover, Kenneth D.; Dodge, Michael E.; Ercan, Dalia; Ficarro, Scott B.; Udayakumar, Durga; Gurbani, Deepak; Tae, Hyun Seop; Riddle, Steven M.; Sim, Taebo; Marto, Jarrod A.; Janne, Pasi A.; Crews, Craig M.; Gray, Nathanael S. published their research in Nature Chemical Biology on December 31 ,2014. The article was titled 《Pharmacological targeting of the pseudokinase Her3》.Application of 213743-31-8 The article contains the following contents:

Her3 (also known as ErbB3) belongs to the epidermal growth factor receptor tyrosine kinases and is well credentialed as an anti-cancer target but is thought to be ‘undruggable’ using ATP-competitive small mols. because it lacks appreciable kinase activity. Here we report what is to our knowledge the first selective Her3 ligand, TX1-85-1, that forms a covalent bond with Cys721 located in the ATP-binding site of Her3. We demonstrate that covalent modification of Her3 inhibits Her3 signaling but not proliferation in some Her3-dependent cancer cell lines. Subsequent derivatization with a hydrophobic adamantane moiety demonstrates that the resultant bivalent ligand (TX2-121-1) enhances inhibition of Her3-dependent signaling. Treatment of cells with TX2-121-1 results in partial degradation of Her3 and serendipitously interferes with productive heterodimerization between Her3 with either Her2 or c-Met. These results suggest that small mols. will be capable of perturbing the biol. function of Her3 and ∼60 other pseudokinases found in human cells. The results came from multiple reactions, including the reaction of 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8Application of 213743-31-8)

7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine(cas: 213743-31-8) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Application of 213743-31-8

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Botta, M.; De Angelis, F.; Finizia, G.; Gambacorta, A.; Nicoletti, R. published an article on January 31 ,1985. The article was titled 《6-Alkyl- and 5,6-dialkyl-2-methoxy-4-(3H)-pyrimidinones in the transformations of pyrimidines. Conversion into 2-substituted amino- and 4-chloropyrimidine derivatives》, and you may find the article in Synthetic Communications.Safety of 2-Methoxy-6-methylpyrimidin-4-amine The information in the text is summarized as follows:

Pyrimidinones I [R = H, Me; R1 = Me, or RR1 = (CH2)4] were converted to amino analogs II (R2 = Bu, cyclohexyl, Ph), and chloropyrimidines III were obtained from I and SOCl2. I (R = H, R1 = Me) was treated with NaH and BuNH2 in tetralin to give II (R = H, R1 = Me, R2 = Bu). In the part of experimental materials, we found many familiar compounds, such as 2-Methoxy-6-methylpyrimidin-4-amine(cas: 51870-75-8Safety of 2-Methoxy-6-methylpyrimidin-4-amine)

2-Methoxy-6-methylpyrimidin-4-amine(cas: 51870-75-8) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Safety of 2-Methoxy-6-methylpyrimidin-4-amine

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia