Day: February 9, 2023

Mechanism of decarboxylation of 1,3-dimethylorotic acid. A model for orotidine 5′-phosphate decarboxylase was written by Beak, Peter;Siegel, Brock. And the article was included in Journal of the American Chemical Society in 1976.Reference of 59864-31-2 This article mentions the following:

The decarboxylation of 1,3-dimethylorotic acid (I) is shown to proceed by sep. pH-determined pathways in sulfolane at 180-220°. Although a process involving ionization of I is the major pathway in the presence of excess base, decarboxylation is initiated by zwitterion formation in the neutral solvent. Measurements of the rate of loss of CO2 from 6-carboxy-2,4-dimethoxypyrimidine and 1-methyl-2,4-dimethoxypyrimidinium-6-carboxylate betaine (II) are used to estimate the equilibrium and rate constants for the zwitterionic pathway. Comparison of the rate constant for decarboxylation of II with kcat for orotidine 5′-phosphate decarboxylase shows that the biol. catalysis can be satisfactorily accounted for if the enzyme provides a site which displaces the equilibrium in favor of the zwitterionic form of orotidylic acid. It is also noted that the inhibitor, 6-azauridine monophosphate, which has a greater affinity for the enzyme than does the substrate, provides a partial model for the intermediate formed on loss of CO2 from the zwitterion. In the experiment, the researchers used many compounds, for example, 1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid (cas: 59864-31-2Reference of 59864-31-2).

1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid (cas: 59864-31-2) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Reference of 59864-31-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A directing group-assisted ruthenium-catalyzed approach to access meta-nitrated phenols was written by Sasmal, Sheuli;Sinha, Soumya Kumar;Lahiri, Goutam Kumar;Maiti, Debabrata. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Synthetic Route of C11H9NO This article mentions the following:

Meta-Selective C-H nitration of phenol derivatives RC₆H₄OR¹ (R = H, 4-Me, 2-MeO, 4-Ph, etc.; R¹ = pyridin-2-yl, 5-methylpyridin-2-yl, pyrimidin-2-yl) was developed using a Ru-catalyzed σ-activation strategy. Cu(NO₃)₂.3H₂O was employed as the nitrating source, whereas Ru₂(CO)₁₂ was found to be the most suitable metal catalyst for the protocol. Mechanistic studies suggested involvement of an ortho-CAr-H metal intermediate, which promoted meta-electrophilic aromatic substitution and silver-assisted free-radical pathway. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Synthetic Route of C11H9NO).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Synthetic Route of C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reaction of aromatic N-oxides with dipolarophiles. Part 18. Formation mechanism and x-ray structure of the cycloadduct from sequential pericyclic reaction of pyridine N-oxides with phenylsulfonylallene was written by Matsuoka, Toshikazu;Hasegawa, Tomoaki;Eto, Masashi;Harano, Kazunobu;Hisano, Takuzo. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1993.Application In Synthesis of 3,5-Dimethylpyridine 1-oxide This article mentions the following:

Sequential pericyclic reactions of pyridine N-oxides (1) with phenylsulfonylpropadiene (2) and 1-phenylsulfonylpropyne (3) were investigated. 3,5-Dimethylpyridine N-oxide (1a) and 2 in CHCl₃ at room temperature gave a mixture of the [1,5]-sigmatropic rearrangement product 4a of the 1:1 cycloadduct and the 1:2 azetidine-type cycloadduct 5a. The structure of 5a was determined crystallog. The reaction rate of 1a with 2 was ∼50,000 times that of 1a with N-phenylmaleimide. The reaction of 1a with 3 did not give 5a but 4a as the sole product. The reactivity, regio- and periselectivity, and formation mechanism of 4 and 5 are examined by FMO. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Application In Synthesis of 3,5-Dimethylpyridine 1-oxide).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Application In Synthesis of 3,5-Dimethylpyridine 1-oxide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Structure-based Design of Pyridone-Aminal eFT508 Targeting Dysregulated Translation by Selective Mitogen-activated Protein Kinase Interacting Kinases 1 and 2 (MNK1/2) Inhibition was written by Reich, Siegfried H.;Sprengeler, Paul A.;Chiang, Gary G.;Appleman, James R.;Chen, Joan;Clarine, Jeff;Eam, Boreth;Ernst, Justin T.;Han, Qing;Goel, Vikas K.;Han, Edward Z. R.;Huang, Vera;Hung, Ivy N. J.;Jemison, Adrianna;Jessen, Katti A.;Molter, Jolene;Murphy, Douglas;Neal, Melissa;Parker, Gregory S.;Shaghafi, Michael;Sperry, Samuel;Staunton, Jocelyn;Stumpf, Craig R.;Thompson, Peggy A.;Tran, Chinh;Webber, Stephen E.;Wegerski, Christopher J.;Zheng, Hong;Webster, Kevin R.. And the article was included in Journal of Medicinal Chemistry in 2018.Formula: C6H3BrFNO2 This article mentions the following:

Dysregulated translation of mRNA plays a major role in tumorigenesis. Mitogen-activated protein kinase interacting kinases (MNK)1/2 are key regulators of mRNA translation integrating signals from oncogenic and immune signaling pathways through phosphorylation of eIF4E and other mRNA binding proteins. Modulation of these key effector proteins regulates mRNA, which controls tumor/stromal cell signaling. Compound 23 (eFT508, 6′-((6-aminopyrimidin-4-yl)amino)-8′-methyl-2’H-spiro-[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione hydrochloride), an exquisitely selective, potent dual MNK1/2 inhibitor, was designed to assess the potential for control of oncogene signaling at the level of mRNA translation. The crystal structure-guided design leverages stereoelectronic interactions unique to MNK culminating in a novel pyridone-aminal structure described for the first time in the kinase literature. Compound 23 has potent in vivo antitumor activity in models of diffuse large cell B-cell lymphoma and solid tumors, suggesting that controlling dysregulated translation has real therapeutic potential. Compound 23 is currently being evaluated in Phase 2 clin. trials in solid tumors and lymphoma. Compound 23 is the first highly selective dual MNK inhibitor targeting dysregulated translation being assessed clin. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-fluoropicolinic acid (cas: 669066-91-5Formula: C6H3BrFNO2).

5-Bromo-3-fluoropicolinic acid (cas: 669066-91-5) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Formula: C6H3BrFNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Predictive in silico Modeling of Ionic Liquids toward Inhibition of the Acetyl Cholinesterase Enzyme of Electrophorus electricus: A Predictive Toxicology Approach was written by Das, Rudra Narayan;Roy, Kunal. And the article was included in Industrial & Engineering Chemistry Research in 2014.Related Products of 17281-59-3 This article mentions the following:

Chems. are the essential components of the industry for maneuvering the required need of the living ecosystem. Ionic liquids are a group of promising novel chems. with potential usefulness toward various industrial applications, although they are not entirely devoid of hazardous outcomes. The present study is an attempt to investigate the chem. attributes of a wide variety of 292 ionic liquids toward their inhibitory potential of acetyl cholinesterase enzyme of elec. eel through the development of predictive regression and classification-based quant. math. models in the light of the OECD guidelines. Mol. docking studies have addnl. corroborated the results. Hydrophilicity, hydrophobicity, branching, and pos. charged N-species were observed to be the major chem. contributors to such toxicity. The docking studies chiefly portrayed the π-cationic type interaction of the cationic N⁺ atom with the Phe 288, Phe 290, and Trp 23 residues of the acyl binding pocket to be responsible for enzyme inhibition. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3Related Products of 17281-59-3).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Related Products of 17281-59-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Visible light-induced aerobic C-N bond activation: a photocatalytic strategy for the preparation of 2-arylpyridines and 2-arylquinolines was written by Hu, Bei;Li, Yuyuan;Dong, Wuheng;Xie, Xiaomin;Wan, Jun;Zhang, Zhaoguo. And the article was included in RSC Advances in 2016.Category: pyridine-derivatives This article mentions the following:

An efficient method for accessing arylpyridines, e.g., I and arylquinolines, e.g., II via visible light-induced aerobic C-N bond activation is described. The applicability of different kinds of simple ketones such as 1-(2-methoxyphenyl)ethanone, 1-tetralone, 1-(2-pyridinyl)ethanone, etc. easily available amines (such as, diaminopropane, 2-aminobenzylamine), and the use of air as the sole oxidant make this transformation very attractive. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Category: pyridine-derivatives).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Express photolithographic DNA microarray synthesis with optimized chemistry and high-efficiency photolabile groups was written by Sack, Matej;Hoelz, Kathrin;Holik, Ann-Katrin;Kretschy, Nicole;Somoza, Veronika;Stengele, Klaus-Peter;Somoza, Mark M.. And the article was included in Journal of Nanobiotechnology in 2016.Reference of 628-13-7 This article mentions the following:

Background: DNA microarrays are a core element of modern genomics research and medical diagnostics, allowing the simple and simultaneous determination of the relative abundances of hundreds of thousands to millions of genomic DNA or RNA sequences in a sample. Photolithog. in situ synthesis, using light projection from a digitally-controlled array of micromirrors, has been successful at both com. and laboratory scales. The advantages of this synthesis method are its ability to reliably produce high-quality custom microarrays with a very high spatial d. of DNA features using a compact device with few moving parts. The phosphoramidite chem. used in photolithog. synthesis is similar to that used in conventional solid-phase synthesis of oligonucleotides, but some unique differences require an independent optimization of the synthesis chem. to achieve fast and low-cost synthesis without compromising microarray quality. Results: High microarray quality could be maintained while reducing coupling time to a few seconds using DCI activator. Five coupling activators were compared, which resulted in microarray hybridization signals following the order ETT > Activator 42 > DCI [Much Greather Than] BTT [Much Greather Than] pyridinium chloride, but only the use of DCI led to both high signal and highly uniform feature intensities. The photodeprotection time was also reduced to a few seconds by replacing the NPPOC photolabile group with the new thiophenyl-NPPOC group. Other chem. parameters, such as oxidation and washing steps were also optimized. Conclusions: Highly optimized and microarray-specific phosphoramidite chem., along with the use of the very photosensitive thiophenyl-NPPOC protecting group allow for the synthesis of high-complexity DNA arrays using coupling times of 15 s and deprotection times of 9 s. The resulting overall cycle time (coupling to coupling) of about 50 s, results in a three-fold reduction in synthesis time. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Reference of 628-13-7).

Pyridinehydrochloride (cas: 628-13-7) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Reference of 628-13-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A thermochemical computational study on hydroxyquinolines and their azulene analogues was written by Meshhal, Moyassar M.;El-Demerdash, Safinaz H.;El-Nahas, Ahmed M.. And the article was included in Journal of Molecular Structure in 2019.Related Products of 626-64-2 This article mentions the following:

Ab initio CBS-QB3 method has been used to determine gas-phase enthalpies of formation for 34 compounds including a number of hydroxyquinoline isomers, the corresponding azulene analogs and their parent systems. The mean absolute deviation of 4.43 kJ/mol reveals good agreement between our results and the available exptl. data. Relative thermodn. stabilities of hydroxyquinoline isomers and related analogs were discussed and several isomerization reactions enthalpies were derived. The same level of theory has also been utilized to calculate adiabatic ionization energies and electron affinities for the mols. with known exptl. values and the agreement between theory and experiment was found to be within 8 kJ/mol. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Related Products of 626-64-2).

Pyridin-4-ol (cas: 626-64-2) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Related Products of 626-64-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Graphene Oxide as a Carbocatalyst for Sustainable ipso-Hydroxylation of Arylboronic Acids: A Simple and Straightforward Strategy To Access Phenols was written by Karthik, Murugan;Suresh, Palaniswamy. And the article was included in ACS Sustainable Chemistry & Engineering in 2019.Safety of Pyridin-4-ol This article mentions the following:

A metal-free and straightforward protocol for the synthesis of phenols from aryl and heteroaryl boronic acids has been demonstrated using graphene oxide as a carbocatalyst. This sustainable ipso-hydroxylation takes place under mild conditions using aqueous H₂O₂ as an oxidant in a water medium in a short time under organocatalytic and base-free conditions. The control experiments reveal that the presence of carboxyl groups promotes ipso-hydroxylation. The developed methodol. offers GO as a benign solid-acid catalyst with good sustainability which can be reused several times without significant loss in its catalytic activities; this was proven by the Fourier transform IR and powder X-ray diffraction studies of the reused catalyst. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Safety of Pyridin-4-ol).

Pyridin-4-ol (cas: 626-64-2) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Safety of Pyridin-4-ol

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Metal-free oxidative C(sp³)-H functionalization: a facile route to quinoline formaldehydes from methyl-azaheteroarenes was written by Weng, Wei-Zhao;Guo, Jiang-Shan;Liu, Kai-Xuan;Shao, Tian-Qi;Song, Li-Qun;Zhu, Yan-Ping;Sun, Yuan-Yuan;Meng, Qing-Guo. And the article was included in Canadian Journal of Chemistry in 2020.HPLC of Formula: 91-02-1 This article mentions the following:

A facile protocol for the synthesis of quinoline formaldehydes, e.g., I via direct oxidative C-H bond functionalization of methyl-azaheteroarenes in the presence of I₂-DMSO has been described. This method is metal-free and easy to operate. This reaction provided a convenient route for the preparation of a range of important quinoline formaldehydes. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1HPLC of Formula: 91-02-1).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. HPLC of Formula: 91-02-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem