Day: October 13, 2022

Maruyama, Tatsuya; Onda, Kenichi; Hayakawa, Masahiko; Matsui, Tetsuo; Takasu, Toshiyuki; Ohta, Mitsuaki published an article in European Journal of Medicinal Chemistry. The title of the article was 《Discovery of novel acetanilide derivatives as potent and selective β3-adrenergic receptor agonists》.Recommanded Product: 63155-11-3 The author mentioned the following in the article:

In the search for potent and selective human β3-adrenergic receptor (AR) agonists as potential drugs for the treatment of obesity and noninsulin-dependent (type II) diabetes, a novel series of acetanilide-based analogs were prepared and their biol. activities were evaluated at the human β3-, β2-, and β1-ARs. Among these compounds, 2-pyridylacetanilide, pyrimidin-2-ylacetanilide, and pyrazin-2-ylacetanilide derivatives exhibited potent agonistic activity at the β3-AR with functional selectivity over the β1- and β2-ARs. In particular, pyrimidin-2-ylacetanilide was found to be the most potent and selective β3-AR agonist with an EC50 value of 0.11 μM and no agonistic activity for either the β1- or β2-AR. In addition, these three compounds showed significant hypoglycemic activity in a rodent diabetic model. In the part of experimental materials, we found many familiar compounds, such as Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3Recommanded Product: 63155-11-3)

Ethyl 2-(pyrimidin-2-yl)acetate(cas: 63155-11-3) 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.Recommanded Product: 63155-11-3

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The author of 《Formation of Pyrimidines by Use of Nitromalonic Aldehyde》 were Hale, William J.; Brill, Harvey C.. And the article was published in Journal of the American Chemical Society in 1912. Product Details of 14001-69-5 The author mentioned the following in the article:

Urea and Na nitromalonic aldehyde in H2O condense in presence of a little piperidine to nitromalonic aldehyde monoureide, NH2CON : C2H2(NO2)CHO, m. 154° (corrected). Sodium salt + 3 H2O. On passing dry HCl into an alc. solution of nitromalonic aldehyde nonanil and urea, there appeared nitromalonic aldehyde ureideanil, PhN : CCH(NO2)CH:NCONH2, red, needle-like crystals m. 211° (corrected). Nitromalonic aldehyde ureideoxime, yellow leaf-like crystals, m. 174-5° (corrected). On treating the monourcide with phenylhydrazine, the urea nucleus was displaced and 1-phenyl-4-nitropyrazole resulted. The mother liquor from the nitromalonic aldehyde monureide on standing slowly deposited 5-nitro-2-hydroxypyrimidine, HOC : NCH : CNO2, small yellow plates, m. 203.5° (corrected). Sodium salt + 2 H2O, red crystals. Potassium salt + H2O yellow prismatic crystals. Barium salt + 4 H2O, reddish brown. Silver salt, reddish yellow color. On warming the Na salt with MeI in alc., 5-nitro-2-methoxypyrimidine, platelike crystals m. 168-9° (corrected). Benzamidine hydrochloride, and Na nitromalonic nldehyde in H2O gave 5-nitro-2-phenylpyrimidine, soft plates m. 219° (corrected). Guanidine carbonate and Na nitromalonic aldehyde in presence of a little piperidine give a quant. yield of 5-nitro-2-aminopyrimidine, colorless needles, m. 236° (corrected); on b. with alkali, NH3 is evolved. 5-Nitro-2-acetylaminopyrimidine, crystals, m. 172-5° (corrected). On adding a little KOH to 5-nitro-2-aminopyrimidine in CS2, 5,5′-dinitro-2,2′-dipyrimidylthiocarbamide, leaflets, m. 230-1° (corrected) was obtained. Nitromalonic aldehyde monophenylureide, crystalline, 176-7° (corrected). Nitromalonic aldehyde monobenzylureide, crystalline, m. 150-1° (corrected). Nitromalonic aldehyde monomethylureide, yellow crystals. In the experimental materials used by the author, we found 2-Methoxy-5-nitropyrimidine(cas: 14001-69-5Product Details of 14001-69-5)

2-Methoxy-5-nitropyrimidine(cas: 14001-69-5) is a member of ether. Friedel Crafts reaction, for example, adds an alkyl or acyl group to aromatic ethers when they react with an alkyl or acyl halide in the presence of a Lewis acid as a catalyst.Product Details of 14001-69-5

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 2019,Journal of the American Chemical Society included an article by Fawcett, Alexander; Murtaza, Amna; Gregson, Charlotte H. U.; Aggarwal, Varinder K.. Computed Properties of C4H2Cl2N2. The article was titled 《Strain-Release-Driven Homologation of Boronic Esters: Application to the Modular Synthesis of Azetidines》. The information in the text is summarized as follows:

Azetidines are important motifs in medicinal chem., but there are a limited number of methods for their synthesis. Herein, the authors present a new method for their modular construction by exploiting the high ring strain associated with azabicyclo[1.1.0]butane. Generation of azabicyclo[1.1.0]butyl lithium followed by its trapping with a boronic ester gives an intermediate boronate complex which, upon N-protonation with acetic acid, undergoes 1,2-migration with cleavage of the central C-N bond to relieve ring strain. The methodol. is applicable to primary, secondary, tertiary, aryl, and alkenyl boronic esters and occurs with complete stereospecificity. The homologated azetidinyl boronic esters can be further functionalized through reaction of the N-H azetidine, and through transformation of the boronic ester. The methodol. was applied to a short, stereoselective synthesis of the azetidine-containing pharmaceutical, cobimetinib. After reading the article, we found that the author used 2,4-Dichloropyrimidine(cas: 3934-20-1Computed Properties of C4H2Cl2N2)

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.Computed Properties of C4H2Cl2N2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

《Synthesis, characterization and biological evaluation of some novel carboxamide derivatives of pyrazole》 was published in World Journal of Pharmaceutical Research in 2020. These research results belong to Arvadiya, Abhishek; Patel, Bony; Patel, Khyati; Zala, Mayursinh. Product Details of 1193-21-1 The article mentions the following:

A series of I [R = Ph, 4-fluorophenyl,…etc] was synthesized by using different acids. All steps were synthesized by green procedure with excellent yield. Product obtained were characterised by means of the NMR, IR and Mass spectral anal. The synthesized compounds were evaluated for their in-vitro antimicrobial activity against different bacterial and fungal strains using Mueller-Hinton Broth dilution method and also invitro antitubercular activity was performed. The results came from multiple reactions, including the reaction of 4,6-Dichloropyrimidine(cas: 1193-21-1Product Details of 1193-21-1)

4,6-Dichloropyrimidine(cas: 1193-21-1) 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.Product Details of 1193-21-1

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

《A Predictive Model Towards Site-Selective Metalations of Functionalized Heterocycles, Arenes, Olefins, and Alkanes using TMPZnCl·LiCl》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Balkenhohl, Moritz; Jangra, Harish; Makarov, Ilya S.; Yang, Shu-Mei; Zipse, Hendrik; Knochel, Paul. Category: pyrimidines The article mentions the following:

The development of a predictive model towards site-selective deprotometalation reactions using TMPZnCl·LiCl is reported (TMP = 2,2,6,6-tetramethylpiperidinyl). The pKa values of functionalized N-, S-, and O-heterocycles, arenes, alkenes, or alkanes were calculated and compared to the exptl. deprotonation sites. Large overlap (>80%) between the calculated and empirical deprotonation sites was observed, showing that thermodn. factors strongly govern the metalation regioselectivity. In the case of olefins, calculated frozen state energies of the deprotonated substrates allowed a more accurate prediction. Addnl., various new N-heterocycles were analyzed and the metalation regioselectivities rationalized using the predictive model. After reading the article, we found that the author used 2,4,6-Trichloropyrimidine(cas: 3764-01-0Category: pyrimidines)

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.Category: pyrimidines

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Category: pyrimidinesIn 2021 ,《Novel pyrimidine derivatives as potential anticancer agents: synthesis, biological evaluation and molecular docking study》 appeared in International Journal of Molecular Sciences. The author of the article were Tylinska, Beata; Wiatrak, Benita; Czyznikowska, Zaneta; Ciesla-Niechwiadowicz, Aneta; Gebarowska, Elzbieta; Janicka-Klos, Anna. The article conveys some information:

In the present paper, new pyrimidine derivatives were designed, synthesized and analyzed in terms of their anticancer properties. The tested compounds were evaluated in vitro for their antitumor activity. The cytotoxic effect on normal human dermal fibroblasts (NHDF) was also determined According to the results, all the tested compounds exhibited inhibitory activity on the proliferation of all lines of cancer cells (colon adenocarcinoma (LoVo), resistant colon adenocarcinoma (LoVo/DX), breast cancer (MCF-7), lung cancer (A549), cervical cancer (HeLa), human leukemic lymphoblasts (CCRF-CEM) and human monocytic (THP-1)). In particular, their feature stronger influence on the activity of P-glycoprotein of cell cultures resistant to doxorubicin than doxorubicin. Tested compounds have more lipophilic character than doxorubicin, which determines their affinity for the mol. target and passive transport through biol. membranes. Moreover, the inhibitory potential against topoisomerase II and DNA intercalating properties of synthesized compounds were analyzed via mol. docking. The experimental part of the paper was very detailed, including the reaction process of 4,6-Dichloropyrimidine(cas: 1193-21-1Category: pyrimidines)

4,6-Dichloropyrimidine(cas: 1193-21-1) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Category: pyrimidines

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of C5H5N3O3On October 31, 1983 ,《Sigma complexes in the pyrimidine series. 6. Reaction of 5-nitro-2-methoxy- and 5-nitro-4,6-dimethoxypyrimidines with acetylacetone carbanion》 appeared in Khimiya Geterotsiklicheskikh Soedinenii. The author of the article were Remennikov, G. Ya.; Kiselenko, A. A.; Cherkasov, V. M.. The article conveys some information:

Methoxynitropyrimidine I reacted with acetylacetone carbanion to form salt II or acetophenone III, depending on the reaction conditions. Dimethoxynitropyrimidine IV (R = MeO) was not converted to salt V by this reaction; V could be obtained from IV [R = (MeCO)2CH]. The conversion of acetonylpyrimidine VI to salt VII was also described. The results came from multiple reactions, including the reaction of 2-Methoxy-5-nitropyrimidine(cas: 14001-69-5Synthetic Route of C5H5N3O3)

2-Methoxy-5-nitropyrimidine(cas: 14001-69-5) 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.Synthetic Route of C5H5N3O3

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Remennikov, G. Ya.; Kurilenko, L. K.; Boldyrev, I. V.; Cherkasov, V. M. published their research in Khimiya Geterotsiklicheskikh Soedinenii on December 31 ,1987. The article was titled 《Sigma complexes in the pyrimidine series. 8. Recyclization of acetonyl anionic σ-complexes of 5-nitropyrimidine and its derivatives》.SDS of cas: 14001-69-5 The article contains the following contents:

Recyclization of title anions I (R = H, MeO, Et2N; R1 = H; cation not specified) with base, e.g., Et4NOH, gave 19-75% 4-O2NC6H4OH. A bicyclic mechanism was proposed. I (R = H, R1 = OMe) and 2-acetonyl analog II did not recyclize under these conditions. Treating methoxynitropyrimidine III (R = MeO, R2 = H) with Et2NH in refluxing MeOH gave 98% III (R = Et2N, R2 = H) (IV), which gave 68.5% I (R = Et2N, R1 = H) (V) with KOH in Me2CO. Oxidation of V with DDQ in Me2CO gave 43% III (R = Et2N, R2 = CH2COMe) (VI) and 28% IV. Deacylation of acetylacetonylidene analog VII with Et2NH in MeOH gave 74.5% VI and 5% III (R = Et2N, R2 = Me).2-Methoxy-5-nitropyrimidine(cas: 14001-69-5SDS of cas: 14001-69-5) was used in this study.

2-Methoxy-5-nitropyrimidine(cas: 14001-69-5) is a member of ether. Friedel Crafts reaction, for example, adds an alkyl or acyl group to aromatic ethers when they react with an alkyl or acyl halide in the presence of a Lewis acid as a catalyst.SDS of cas: 14001-69-5

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In 2015,Sythana, Suresh Kumar; Bhagat, Pundlik R. published 《Metal free C-O bond formation in electron deficient aromatic compounds mediated by tetrabutylammonium hydroxide : application to nimesulide and paracetamol》.Journal of the Indian Chemical Society published the findings.Category: pyrimidines The information in the text is summarized as follows:

A mild and efficient method for carbon-oxygen bond formation for the synthesis of aryl ethers has been demonstrated via reaction of aromatic chloro compounds and alcs. mediated by tetrabutylammonium hydroxide (TBAH). The protocol is free from the metal alkoxides, inorganic bases or metal catalysts. This methodol. has been applied for synthesis of paracetamol and nimesulide intermediates. After reading the article, we found that the author used 2,4,6-Trichloropyrimidine(cas: 3764-01-0Category: pyrimidines)

2,4,6-Trichloropyrimidine(cas: 3764-01-0) 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.Category: pyrimidines

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

《A Convenient Late-Stage Fluorination of Pyridylic C-H Bonds with N-Fluorobenzenesulfonimide》 was published in Angewandte Chemie, International Edition in 2016. These research results belong to Meanwell, Michael; Nodwell, Matthew B.; Martin, Rainer E.; Britton, Robert. Synthetic Route of C6H7BrN2 The article mentions the following:

Pyridine features prominently in pharmaceuticals and drug leads, and methods to selectively manipulate pyridine basicity or metabolic stability are highly sought after. A robust, metal-free direct fluorination of unactivated pyridylic C-H bonds was developed. This convenient reaction shows high functional-group tolerance and offers complimentary selectivity to existing C-H fluorination strategies. Importantly, this late-stage pyridylic C-H fluorination provides opportunities to rationally modulate the basicity, lipophilicity, and metabolic stability of alkylpyridine drugs. Thus, e.g., mixing 4-ethylpyridine with NFSI in MeCN afforded 4-(1-fluoroethyl)pyridine (87%). The results came from multiple reactions, including the reaction of 5-Bromo-4-ethylpyrimidine(cas: 951884-36-9Synthetic Route of C6H7BrN2)

5-Bromo-4-ethylpyrimidine(cas: 951884-36-9) 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.Synthetic Route of C6H7BrN2

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia