Day: January 5, 2023

Synthesis of 2,5-thiazole butanoic acids as potent and selective α_vβ₃ integrin receptor antagonists with improved oral pharmacokinetic properties was written by Wendt, John A.;Wu, Hongwei;Stenmark, Heather G.;Boys, Mark L.;Downs, Victoria L.;Penning, Thomas D.;Chen, Barbara B.;Wang, Yaping;Duffin, Tiffany;Finn, Mary Beth;Keene, Jeffery L.;Engleman, V. Wayne;Freeman, Sandra K.;Hanneke, Melanie L.;Shannon, Kristen E.;Nickols, Maureen A.;Steininger, Christina N.;Westlin, Marissa;Klover, Jon A.;Westlin, William;Nickols, G. Allen;Russell, Mark A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2006.Quality Control of 3-Hydroxy-6-methyl-2-nitropyridine This article mentions the following:

A series of 2,5-thiazoles, e.g. I [R = 3-FC₆H₄, 3,4-(MeO)₂C₆H₃, 6-methoxy-3-pyridyl, 2-phenyl-5-thiazolyl, etc.], which are potent antagonists of the integrin α_vβ₃ and show selectivity relative to the other integrins, such as α_IIbβ₃ and α_vβ₆, has been synthesized. These analogs were demonstrated to have high bioavailability relative to other relative heterocyclic analogs. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-6-methyl-2-nitropyridine (cas: 15128-90-2Quality Control of 3-Hydroxy-6-methyl-2-nitropyridine).

3-Hydroxy-6-methyl-2-nitropyridine (cas: 15128-90-2) 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). Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Quality Control of 3-Hydroxy-6-methyl-2-nitropyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of m-Alkylphenols via a Ruthenium-Catalyzed C-H Bond Functionalization of Phenol Derivatives was written by Li, Gang;Gao, Panpan;Lv, Xulu;Qu, Chen;Yan, Qingkai;Wang, Ya;Yang, Suling;Wang, Junjie. And the article was included in Organic Letters in 2017.Quality Control of 2-Phenoxypyridine This article mentions the following:

In the presence of [RuCl₂(p-cymene)]₂ and 1-adamantanecarboxylic acid, aryl 2-pyridinyl ethers underwent regioselective alkylation with secondary and tertiary alkyl bromides mediated by K₂CO₃ in benzene to provide m-alkylaryl 2-pyridinyl ethers in 33-73% yields; N-methylation of the pyridine moiety with Me triflate followed by hydrolysis yielded m-alkylated phenols such as 3-tert-butylphenol in 74-82% yields. The method was used to prepare the pesticide etoxazole via 3-tert-butylphenol. A (p-cymene)ruthenium complex of 2-phenoxypyridine was prepared and underwent regioselective alkylation to give 3-(3-pentyl)phenyl 2-pyridinyl ether under the standard reaction conditions; addition of TEMPO, BHT, or benzoquinone inhibited the reaction. The structure of the (p-cymene)ruthenium complex of 2-phenoxypyridine was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Quality Control of 2-Phenoxypyridine).

2-Phenoxypyridine (cas: 4783-68-0) 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. 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. Quality Control of 2-Phenoxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Trimethylsilanol as a leaving group; III. A simple one-step conversion of aromatic heterocyclic N-oxides to α-cyano aromatic N-heterocycles was written by Vorbrueggen, Helmut;Krolikiewicz, Konrad. And the article was included in Synthesis in 1983.Recommanded Product: 1620-76-4 This article mentions the following:

Heterocyclic N-oxides such as pyridine or quinoline N-oxides were treated with Me₃SiCN in the presence of Et₃N in MeCN to give α-cyano heterocycles. The strong affinity of the hard Me₃Si group for the hard N-oxide moiety and the soft CN group for the adjacent soft α-C atom was apparently the driving force for the selective α-addition of Me₃SiCN to the heterocyclic N-oxide, followed by elimination of Me₃SiOH as a leaving group. Thus, pyridine N-oxide added Me₃SiCN to give 80% 2-cyanopyridine. Among the ∼10 other compounds similarly prepared were 2-cyano-4-methylpyridine, 2-cyano-3-hydroxypyridine and 2-cyanoquinoline. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4Recommanded Product: 1620-76-4).

4-Methylpicolinonitrile (cas: 1620-76-4) 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. 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.Recommanded Product: 1620-76-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The Impact of the Interplay between Steric and Electronic Effects on the Synthesis and Optical Properties of Diketopyrrolopyrroles Bearing Pyridine Moieties was written by Vakuliuk, Olena;Purc, Anna;Clermont, Guillaume;Blanchard-Desce, Mireille;Gryko, Daniel T.. And the article was included in ChemPhotoChem in 2017.Related Products of 3939-12-6 This article mentions the following:

The influence of a combination of steric and electronic factors on both the preparation and the optical properties of diketopyrrolopyrroles was investigated. The attachment of a cyano group to the electron-deficient pyridine ring overcame the neg. influence of the flanking Me group on the efficiency of the synthesis of diketopyrrolopyrroles. Diketopyrrolopyrroles possessing pyridine-N-oxide moieties were studied for the first time. We have also shown that reactions of cyanopyridines possessing an addnl. dialkylamino group were very capricious and depending on the relative position of all substituents, can lead to low yields of diketopyrrolopyrroles. The interplay between the dihedral angle between the diketopyrrolopyrrole core and the pyridyl substituents as well as the presence and position of electron-donating moieties made it possible to modulate the photophys. properties of N,N’-dialkyldiketopyrrolopyrroles. In particular, it was found that pyridine-N-oxides as the aryl moieties had a strong influence on the optical properties of diketopyrrolopyrroles, shifting both absorption and emission bands bathochromically. Two-photon absorption cross-sections had low values except for those dyes possessing a clear quadrupolar centrosym. nature. In the experiment, the researchers used many compounds, for example, 6-Fluoronicotinonitrile (cas: 3939-12-6Related Products of 3939-12-6).

6-Fluoronicotinonitrile (cas: 3939-12-6) 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. 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 3939-12-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analysis of nitrogenous organic compounds from mainstream cigarette smoke using low-temperature solvent extraction followed by comprehensive two-dimensional gas chromatography with high-resolution time-of-flight mass spectrometry was written by Xiang, Zhangmin;Cai, Kai;Zhou, Shuping;Geng, Zhaoliang;Pan, Wenjie. And the article was included in Journal of Separation Science in 2015.Recommanded Product: 2-Isopropylpyridine This article mentions the following:

A method involving comprehensive two-dimensional gas chromatog. coupled to high-resolution time-of-flight mass spectrometry was developed and applied to the anal. of nitrogenous organic compounds present in mainstream cigarette smoke trapped on self-designed equipment. The samples were prepared using low-temperature solvent extraction under liquid nitrogen and analyzed by comprehensive two-dimensional gas chromatog. with high-resolution time-of-flight mass spectrometry. Important exptl. parameters, such as the type and volume of the extraction solvent and flow rate of smoking, were optimized to improve the anal. parameter. The results indicated that 180 mL of di-Et ether in the low-temperature solvent extraction apparatus system with a 4 mL/min smoke flow rate were the optimal conditions. Then, 85 nitrogenous organic compounds were identified and quantified using a mass spectral library search, accurate mass ion and N-rules of a mol. formula for nitrogen compounds Finally, a comparison of the low temperature solvent extraction and Cambridge filter pad method indicated that more peaks, a higher peak volume and better repeatability were obtained using the low-temperature solvent extraction method. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Recommanded Product: 2-Isopropylpyridine).

2-Isopropylpyridine (cas: 644-98-4) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Recommanded Product: 2-Isopropylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Re^I-Catalyzed highly regio- and stereoselective C-H addition to terminal and internal alkynes was written by Chang, Yu-Che;Prakash, Sekar;Cheng, Chien-Hong. And the article was included in Organic Chemistry Frontiers in 2019.Application In Synthesis of 2-(m-Tolyl)pyridine This article mentions the following:

An effective ortho C-H functionalization of arylpyridines e.g., I and detachable N-pyrimidyl indoles II (R = H, CH₃, C(O)CH₃) by terminal and internal alkynes R¹CCR² (R¹ = H, C₆H₅, CH₃(CH₂)₂, C₆H₅CC; R² = 4-CH₃C₆H₄, (CH₂)₅OH, cyclohexyl, etc.) using a Re(I) catalyst providing an efficient access to various E-selective alkenylation products e.g., III were developed. The catalytic reaction is compatible with various aliphatic alkynes, aromatic terminal alkynes and internal alkynes, and structurally different nitrogen heterocycles. Deuterium-labeling experiments indicate that significant deuterium scrambling occurs with the directing groups and acetylenic sp C-H bonds before the migratory insertion. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Application In Synthesis of 2-(m-Tolyl)pyridine).

2-(m-Tolyl)pyridine (cas: 4373-61-9) 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 derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Application In Synthesis of 2-(m-Tolyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ru-Catalysed C-H Arylation of Indoles and Pyrroles with Boronic Acids: Scope and Mechanistic Studies was written by Sollert, Carina;Devaraj, Karthik;Orthaber, Andreas;Gates, Paul J.;Pilarski, Lukasz T.. And the article was included in Chemistry – A European Journal in 2015.Related Products of 4783-68-0 This article mentions the following:

The Ru-catalyzed C2-H arylation of indoles and pyrroles by using boronic acids under oxidative conditions is reported. This reaction can be applied to tryptophan derivatives and tolerates a wide range of functional groups on both coupling partners, including bromides and iodides, which can be further derivatized selectively. New indole-based ruthenacyclic complexes are described and investigated as possible intermediates in the reaction. Mechanistic studies suggest the on-cycle intermediates do not possess a para-cymene ligand and that the on-cycle metalation occurs through an electrophilic attack by the Ru center. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Related Products of 4783-68-0).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. 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. Related Products of 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Palladium-catalyzed decarboxylative, decarbonylative and dehydrogenative C(sp²)-H acylation at room temperature was written by Hossian, Asik;Manna, Manash Kumar;Manna, Kartic;Jana, Ranjan. And the article was included in Organic & Biomolecular Chemistry in 2017.Recommanded Product: 2-(m-Tolyl)pyridine This article mentions the following:

Over the past few decades, an impressive array of C-H activation methodol. has been developed for organic synthesis. However, due to the inherent inertness of the C-H bonds (e.g. ∼110 kcal mol^-1 for the cleavage of C(aryl)-H bonds) harsh reaction conditions have been realized to overcome high energetic transition states resulting in a limited substrate scope and functional group tolerance. Therefore, the development of mild C-H functionalization protocols is in high demand to exploit the full potential of the C-H activation strategy in the synthesis of a complex mol. framework. Although, electron-rich substrates undergo electrophilic metalation under relatively mild conditions, electron-deficient substrates proceed through a rate-limiting C-H insertion under forcing conditions at high temperature In addition, a stoichiometric amount of toxic silver salt is frequently used in palladium catalysis to facilitate the C-H activation process which is not acceptable from the environmental and industrial standpoint. A Pd(II)-catalyzed decarboxylative C-H acylation of 2-arylpyridines with α-ketocarboxylic acids under mild conditions, is reported. The protocol does not require stoichiometric silver(I) salts as additives and proceeds smoothly at ambient temperature A decarbonylative C-H acylation reaction has also been accomplished using aryl glyoxals as acyl surrogates. Finally, a practical C-H acylation via a dehydrogenative pathway has been demonstrated using com. available benzaldehydes and aqueous hydroperoxides. Acetonitrile is optimal solvent for the acylation reaction at room temperature and has a prominent role in the reaction outcome. Control experiments suggest that the acylation reaction via decarboxylative, decarbonylative and dehydrogenative proceeds through a radical pathway. A practical protocol for the sp² C-H acylation reaction, is disclosed. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Recommanded Product: 2-(m-Tolyl)pyridine).

2-(m-Tolyl)pyridine (cas: 4373-61-9) 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. 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. Recommanded Product: 2-(m-Tolyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Aggregation behavior of ionic liquids in aqueous solutions: effect of alkyl chain length, cations, and anions was written by Singh, Tejwant;Kumar, Arvind. And the article was included in Journal of Physical Chemistry B in 2007.Synthetic Route of C10H16ClN This article mentions the following:

Self aggregation of the ionic liquids, 1-butyl-3-methylimidazolium chloride [C₄mim][Cl], 3-methyl-1-octylimidazolium chloride [C₈mim][Cl], 1-butyl-3-methylimidazolium tetrafluoroborate [C₄mim][BF₄], 1-butyl-3-methylpyridinium chloride [C₄mpy][Cl], in aqueous solution has been investigated through ¹H NMR and steady-state fluorescence spectroscopy. Aggregation properties were determined by application of mass action theory to the concentration dependence of ¹H NMR chem. shifts. Aggregation properties showed fairly good agreement with the previously reported results obtained from small angle neutron scattering, conductivity, and surface tension measurements. A detailed anal. of chem. shifts of water and various protons in ILs has been employed to probe the aggregate structure. Fluorescence spectroscopy provided important information about the critical aggregation concentration (cac) and the microenvironment of the aggregates. The authors could also observe a break point quite consistent with that of ¹H NMR and fluorescence spectroscopy at cac from the concentration dependence of refractive index measurements. Standard free energies of aggregation ΔGmo of various ILs derived using the refractive index/concentration profiles were found comparable to those of classical ionic surfactants. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3Synthetic Route of C10H16ClN).

1-Butyl-3-methylpyridinium Chloride (cas: 125652-55-3) 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.Synthetic Route of C10H16ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents was written by Zhang, Xin-Hui;Bo-Wang;Tao, Yuan-Yuan;Ma, Qin;Wang, Hao-Jie;He, Zhang-Xu;Wu, Hui-Pan;Li, Yi-Han;Zhao, Bing;Ma, Li-Ying;Liu, Hong-Min. And the article was included in European Journal of Medicinal Chemistry in 2020.Application of 91-02-1 This article mentions the following:

A series of thiosemicarbazone derivatives I [R¹ = H, 4-MeO, 2-Br, 3-Br, 4-Br; R² = H, Me, 2-pyridyl, etc.; R³ = 2-furyl, 3-indolyl, 2-pyridyl, etc.; n = 0, 1, 2] containing different aromatic heterocyclic groups was synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds I showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound I [R¹ = 4-MeO, R² = Me, R³ = 2-pyridyl, n = 0] displayed significant advantages in inhibition effect with an IC₅₀ value of 0.031μM, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved resp.). Besides, compound I [R¹ = 4-MeO, R² = Me, R³ = 2-pyridyl, n = 0] showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound I [R¹ = 4-MeO, R² = Me, R³ = 2-pyridyl, n = 0] could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, compound I [R¹ = 4-MeO, R² = Me, R³ = 2-pyridyl, n = 0] could evidently suppressed the cell migration and invasion by blocking the EMT (epithelial-mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives I which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Application of 91-02-1).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) 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. 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 of 91-02-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem