Tag: 100-200

Ru-Catalyzed C-H Arylation of Fluoroarenes with Aryl Halides was written by Simonetti, Marco;Perry, Gregory J. P.;Cambeiro, Xacobe C.;Julia-Hernandez, Francisco;Arokianathar, Jude N.;Larrosa, Igor. And the article was included in Journal of the American Chemical Society in 2016.Product Details of 4783-68-0 This article mentions the following:

Although the ruthenium-catalyzed C-H arylation of arenes bearing directing groups with haloarenes is well-known, this process has never been achieved in the absence of directing groups. We report the first example of such a process and show that unexpectedly the reaction only takes place in the presence of catalytic amounts of a benzoic acid. Furthermore, contrary to other transition metals, the arylation site selectivity is governed by both electronic and steric factors. Stoichiometric and NMR mechanistic studies support a catalytic cycle that involves a well-defined η⁶-arene-ligand-free Ru(II) catalyst. Indeed, upon initial pivalate-assisted C-H activation, the aryl-Ru(II) intermediate generated is able to react with an aryl bromide coupling partner only in the presence of a benzoate additive. In contrast, directing-group-containing substrates (such as 2-phenylpyridine) do not require a benzoate additive. Deuterium labeling and kinetic isotope effect experiments indicate that C-H activation is both reversible and kinetically significant. Computational studies support a concerted metalation-deprotonation (CMD)-type ruthenation mode and shed light on the unusual arylation regioselectivity. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Product Details of 4783-68-0).

2-Phenoxypyridine (cas: 4783-68-0) 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.Product Details of 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Facile C-H arylation using catalytically active terminal sulfurs of 2 dimensional molybdenum disulfide was written by Hwang, Eunhee;Mi Lee, Sae;Bak, Sora;Min Hwang, Hee;Kim, Hyunjung;Lee, Hyoyoung. And the article was included in Tetrahedron Letters in 2018.Application of 4373-61-9 This article mentions the following:

The first methodol. of C-H arylation of heteroarene via 2D transition metal dichalcogenides that have catalytically active edge functional groups was described. The terminal sulfur groups could effectively catalyze a formation of an azo-linked intermediate with aryl diazonium salts, leading to produce heteroarenes with good yields. This novel methodol. using bulk 2D transition metal dichalcogenides that have catalytically active edge functional groups can apply for various reactions to achieve C-C bond formation in the fields of heterogeneous catalysis that is easily separable, highly reusable, and inexpensive method. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Application of 4373-61-9).

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. 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.Application of 4373-61-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Discovery of BNC375, a Potent, Selective, and Orally Available Type I Positive Allosteric Modulator of α7 nAChRs was written by Harvey, Andrew J.;Avery, Thomas D.;Schaeffer, Laurent;Joseph, Christophe;Huff, Belinda C.;Singh, Rajinder;Morice, Christophe;Giethlen, Bruno;Grishin, Anton A.;Coles, Carolyn J.;Kolesik, Peter;Wagner, Stephanie;Andriambeloson, Emile;Huyard, Bertrand;Poiraud, Etienne;Paul, Dharam;O’Connor, Susan M.. And the article was included in ACS Medicinal Chemistry Letters in 2019.Reference of 28020-37-3 This article mentions the following:

Pos. allosteric modulators (PAMs) of α7 nAChRs can have different properties with respect to their effects on channel kinetics. Type I PAMs amplify peak channel response to acetylcholine but do not appear to influence channel desensitization kinetics, whereas Type II PAMs both increase channel response and delay receptor desensitization. Both Type I and Type II PAMs are reported in literature, but there are limited reports describing their structure-kinetic profile relationships. Here, we report a novel class of compounds with either Type I or Type II behavior that can be tuned by the relative stereochem. around the central cyclopropyl ring: for example, (R,R)-13 (BNC375) and its analogs with RR stereochem. around the central cyclopropyl ring are Type I PAMs, whereas compounds in the same series with SS stereochem. (e.g., (S,S)-13) are Type II PAMs as measured using patch-clamp electrophysiol. Further fine control over the kinetics has been achieved by changing the substitutions on the aniline ring: generally the substitution of aniline with strong electron withdrawing groups reduces the Type II character of these compounds Our structure-activity optimization efforts have led to the discovery of BNC375, a small mol. with good CNS-drug like properties and clin. candidate potential. In the experiment, the researchers used many compounds, for example, 3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3Reference of 28020-37-3).

3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3) 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Reference of 28020-37-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Structure-activity studies related to ABT-594, a potent nonopioid analgesic agent: effect of pyridine and azetidine ring substitutions on nicotinic acetylcholine receptor binding affinity and analgesic activity in mice was written by Holladay, Mark W.;Bai, Hao;Li, Yihong;Lin, Nan-Horng;Daanen, Jerome F.;Ryther, Keith B.;Wasicak, James T.;Kincaid, John F.;He, Yun;Hettinger, Anne-Marie;Huang, Peggy;Anderson, David J.;Bannon, Anthony W.;Buckley, Michael J.;Campbell, Jeffrey E.;Donnelly-Roberts, Diana L.;Gunther, Karen L.;Kim, David J. B.;Kuntzweiler, Theresa A.;Sullivan, James P.;Decker, Michael W.;Arneric, Stephen P.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1998.Recommanded Product: 51834-97-0 This article mentions the following:

Analogs of A-98593 (I) and its enantiomer ABT-594 (II) with diverse substituents on the pyridine ring were prepared and tested for affinity to nicotinic acetylcholine receptor binding sites in rat brain and for analgesic activity in the mouse hot plate assay. Numerous types of modifications were consistent with high affinity for [³H]cytisine binding sites. By contrast, only selected modifications resulted in retention of analgesic potency in the same range as I and II. Analogs of II with one or two Me substituents at the 3-position of the azetidine ring also were prepared and substantially less active in both assays. In the experiment, the researchers used many compounds, for example, 5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0Recommanded Product: 51834-97-0).

5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. 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.Recommanded Product: 51834-97-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Enzyme-like Supramolecular Iridium Catalysis Enabling C-H Bond Borylation of Pyridines with meta-Selectivity was written by Trouve, Jonathan;Zardi, Paolo;Al-Shehimy, Shaymaa;Roisnel, Thierry;Gramage-Doria, Rafael. And the article was included in Angewandte Chemie, International Edition in 2021.Application In Synthesis of Pyridinehydrochloride This article mentions the following:

The use of secondary interactions between substrates and catalysts is a promising strategy to discover selective transition metal catalysts for atom-economy C-H bond functionalization. The most powerful catalysts are found via trial-and-error screening due to the low association constants between the substrate and the catalyst in which small stereo-electronic modifications within them can lead to very different reactivities. To circumvent these limitations and to increase the level of reactivity prediction in these important reactions, the authors report herein a supramol. catalyst harnessing Zn···N interactions that binds to pyridine-like substrates as tight as it can be found in some enzymes. The distance and spatial geometry between the active site and the substrate binding site is ideal to target unprecedented meta-selective iridium-catalyzed C-H bond borylations with enzymic Michaelis-Menten kinetics, besides unique substrate selectivity and dormant reactivity patterns. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Application In Synthesis of Pyridinehydrochloride).

Pyridinehydrochloride (cas: 628-13-7) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Application In Synthesis of Pyridinehydrochloride

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

2-Pyridineformamide N(4)-ring incorporated thiosemicarbazones inhibit MCF-7 cells by inhibiting JNK pathway was written by Shakya, Bhushan;Shahi, Nerina;Ahmad, Faiz;Yadav, Paras Nath;Pokharel, Yub Raj. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Application of 1620-76-4 This article mentions the following:

In an effort to develop a more potent anticancer therapeutic agent, a series of 2-pyridineformamide thiosemicarbazones (I) (R = H, 4-CH₃, 5-F, 6-CH₃; heterocycle = pyrrolidine, piperidine, morpholine, thiomorpholine, azepane, 1-(2-pyridinyl)-piperazine) have been synthesized and evaluated for their anti-cancer activities against the cancer cells MCF-7 (breast cancer cell line), A-431 and A375 (epidermoid carcinoma cell line), and HeLa (cervical cancer cell line) using MTT assay. All these 2-pyridineformamide thiosemicarbazones exhibited anti-proliferative activities towards these cell lines. 5FAmPyrr(II) possess most profound effects against MCF-7 cells with IC₅₀ of 0.9 μM. In flow cytometry using Propidium Iodide, II was found to induce cell death significantly in a dose dependent manner (100 nM-3 μM) and inhibited colony formation of MCF-7 cells. This compound induced pro-apoptotic protein Bax and inhibited anti apoptotic protein Bcl-2 as well as both c-Jun and Jun N-terminal kinase (abbreviated as JNK) in concentration dependent manner. Further pro-caspase 3 and PARP were inhibited by II at concentration of 3 μM. The results suggest that II exhibit anticancer potency and induced cell death by inhibiting MAPK signaling and inducing intrinsic apoptotic pathway. All these indicate that 2-pyridineformamide thiosemicarbazones could be developed as future therapeutics agents to treat cancer. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4Application of 1620-76-4).

4-Methylpicolinonitrile (cas: 1620-76-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. 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. Application of 1620-76-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Rhodium(III)-Catalyzed Acylation of C(sp³)-H bonds with Cyclopropenones was written by Kong, Lingheng;Zhou, Xukai;Xu, Youwei;Li, Xingwei. And the article was included in Organic Letters in 2017.Reference of 644-98-4 This article mentions the following:

Rh(III)-catalyzed activation and acylation of sp³ C-H bonds has been realized with diarylcyclopropenone as an acylating reagent. Both benzylic C-H in 8-methylquinolines and unactivated C-H in 2-alkylpyridines are applicable in this C-H acylation reaction, providing enones in good yields under redox-neutral conditions. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Reference of 644-98-4).

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. 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. Reference of 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A novel synthetic scheme for 2-ethylthioisonicotinamide was written by Wang, Cheng-Hsia;Hwang, Fang-Yu;Horng, Jhy-Ming;Chen, Chao-Tung. And the article was included in Heterocycles in 1979.Quality Control of 2-Isopropylpyridine This article mentions the following:

The title compound was prepared by successive ammoxidation of 4-picoline, ethylation of 4-cyanopyridine with Et radicals generated by decarboxylation of EtCO₂H, and treatment of 2-ethylisonicotinonitrile with (NH₄)₂S. A laboratory ammoxidation apparatus is described. Pyridine was alkylated to its 2- and 4-alkyl derivatives and 4-cyanopyridine to its 2-alkyl and 2,6-dialkyl derivatives with alkyl radicals generated from RCO₂H (R = Me, Et, Pr, CHMe₂, Bu). In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Quality Control of 2-Isopropylpyridine).

2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. 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.Quality Control of 2-Isopropylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of propenamides with anti-malarial activities and 3D-QSAR study was written by Cheng, Maosheng;Yan, Dong;Wang, Qianli;Zhang, Li;Shen, Jianmin. And the article was included in Yaoxue Xuebao in 2003.Related Products of 28020-37-3 This article mentions the following:

The 3D-QSAR model of propenamides with anti-malarial activities was presented. The chem. synthesis combined with comparative mol. field anal. (CoMFA) was used. The QSAR models for activities of inhibiting chloroquine resistive malaria (W2) and chloroquine sensitive malaria (D6) were constructed. The activity of anti-W2 was depended mostly on steric interaction and the activity of anti-D6 was depended on both steric and electrostatic interaction. In the experiment, the researchers used many compounds, for example, 3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3Related Products of 28020-37-3).

3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3) 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. 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. Related Products of 28020-37-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ruthenium-Catalyzed meta-C_Ar-H Bond Difluoroalkylation of 2-Phenoxypyridines was written by Jia, Chunqi;Wang, Shichong;Lv, Xulu;Li, Gang;Zhong, Lei;Zou, Lei;Cui, Xiuling. And the article was included in European Journal of Organic Chemistry in 2020.SDS of cas: 4783-68-0 This article mentions the following:

A ruthenium-catalyzed meta-selective C_Ar-H bond difluoroalkylation of 2-phenoxypyridine using 2-bromo-2,2-difluoroacetate has been developed. Mechanistic studies indicated that this difluoroalkylation might involve a radical process. Furthermore, a new method is reported for the synthesis of 2-(meta-difluoroalkylphenoxy)pyridine derivatives, which are present in many pharmaceuticals and other functional compounds In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0SDS of cas: 4783-68-0).

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 groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.SDS of cas: 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem