Month: January 2023

General Copper-Catalyzed Coupling of Alkyl-, Aryl-, and Alkynylaluminum Reagents with Organohalides was written by Shrestha, Bijay;Thapa, Surendra;Gurung, Santosh K.;Pike, Ryan A. S.;Giri, Ramesh. And the article was included in Journal of Organic Chemistry in 2016.Formula: C12H11N This article mentions the following:

We report the first example of a very general Cu-catalyzed cross-coupling of organoaluminum reagents with organohalides. The reactions proceed for the couplings of alkyl-, aryl-, and alkynylaluminum reagents with aryl and heteroaryl halides and vinyl bromides, affording the cross-coupled products in good to excellent yields. Both primary and secondary alkylaluminum reagents can be utilized as organometallic coupling partners. These reactions are not complicated by β-hydride elimination, and as a result rearranged products are not observed with secondary alkylaluminum reagents even for couplings with heteroaryl halides under “ligand-free” conditions. Radical clock experiment with a radical probe and relative reactivity study of Ph₃Al with two haloarenes, 1-bromonaphthalene and 4-chlorobenzonitrile, having two different redox potentials indicates that the reaction does not involve free aryl radicals and radical anions as intermediates. These results combined with the result of the Hammett plot obtained by reacting Ph₃Al with iodoarenes containing p-H, p-Me, p-F, and p-CF₃ substituents, which shows a linear curve (R² = 0.99) with a ρ value of +1.06, suggest that the current transformation follows an oxidative addition-reductive elimination pathway. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Formula: C12H11N).

2-(m-Tolyl)pyridine (cas: 4373-61-9) 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.Formula: C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Chemical microarrays to identify ligands that bind pathogenic cells was written by Barrett, Olivia J.;Childs, Jessica L.;Disney, Matthew D.. And the article was included in ChemBioChem in 2006.Application of 28020-37-3 This article mentions the following:

The use of microarrays to identify new ligands for cells by interrogating their binding to a library of organic ligands is described. The advantages of using microarrays include assay miniaturization and the manner in which ligands are displayed in a small area. This display mimics interactions that occur at cell-cell interfaces and amplifies binding affinities. In addition, a series of array surfaces was tested for resisting nonspecific binding, which includes amine-, BSA, and agarose- (aldehyde-) coated glass, plain glass, and glass coated with ethanolamine prepared in a two-step procedures from amine-coated slides using the pathogenic Pseudomonas aeruginosa, which forms sticky biofilms. The agarose slides offer an alternative as a more general arraying substrate to study the binding of microarray-immobilized ligands to cells. In the experiment, the researchers used many compounds, for example, 3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3Application of 28020-37-3).

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A Practically Unified Electrochemical Strategy for Ni-Catalyzed Decarboxylative Cross-Coupling of Aryl Trimethylammonium Salts was written by Kong, Xianqiang;Chen, Yiyi;Chen, Xiaohui;Lu, Zheng-Xuan;Wang, Wei;Ni, Shao-Fei;Cao, Zhong-Yan. And the article was included in Organic Letters in 2022.Electric Literature of C12H9NO This article mentions the following:

By merging electrocatalysis and nickel catalysis, a unified strategy was successfully applied for preparing aryl ketones ArC(O)Ph [Ar = Ph, 4-ClC₆H₄, 4-MeC₆H₄, etc.], amides ArC(O)NR¹R² [Ar = Ph, 4-ClC₆H₄, 4-MeC₆H₄, etc.; R¹ = R² = Me, Et; R¹R² = CH₂(CH₂)₂CH₂, CH₂CH₂OCH₂CH₂], esters ArC(O)OR [Ar = Ph, 2-MeC₆H₄, 4-FC₆H₄, etc.; R = Me, Et] or aldehydes ArCHO [Ar = Ph, 4-MeC₆H₄, 4-PhC₆H₄, etc.] via decarboxylative cross-coupling of four types of α-oxocarboxylic acids and their derivatives with aryl trimethylammonium salts under mild conditions. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Electric Literature of C12H9NO).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) 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.Electric Literature of C12H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Photosensitive cyclophosphazene and polyphosphazene was written by Bao, Rui;Qiu, Jin-Jun;Liu, Shu-Zheng;Cheng, Tao;Li, Dong;Liu, Cheng-Mei. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2008.COA of Formula: C10H16BrN This article mentions the following:

Functional polyphosphazenes, such as fire retardant materials, high-performance rubber, biopolymer, optical materials and tissue engineering scaffold materials, have been attracted many attentions in recent years. A photosensitive polyphosphazene containing pyridinium groups was reported in this article. The synthesis procedures of preparing photosensitive polyphosphazene with pyridinium unit as side group are carried out. The Mw and Mn of polymer B and polymer C are 4.05 x 10⁶ g/mol and 4.69 × 10⁵ g/mol, resp. For the Polymer C is highly sensitive to light irradiation, it must be kept under dark. Comparing the absorption spectra of polymer B and Polymer C, there is a new absorption spectrum appearing at 357 nm in polymer C2’s curves. It resulted from the formation of conjugated structure. Under UV irradiation, those double bonds underwent cycloaddition reaction to form saturated structure, so the absorption peak at 357 nm decreased with increasing the irradiation time. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6COA of Formula: C10H16BrN).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) 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). 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. COA of Formula: C10H16BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Design, Synthesis, and Biological Evaluation of Potent and Selective Class IIa Histone Deacetylase (HDAC) Inhibitors as a Potential Therapy for Huntington’s Disease was written by Burli, Roland W.;Luckhurst, Christopher A.;Aziz, Omar;Matthews, Kim L.;Yates, Dawn;Lyons, Kathy. A.;Beconi, Maria;McAllister, George;Breccia, Perla;Stott, Andrew J.;Penrose, Stephen D.;Wall, Michael;Lamers, Marieke;Leonard, Philip;Muller, Ilka;Richardson, Christine M.;Jarvis, Rebecca;Stones, Liz;Hughes, Samantha;Wishart, Grant;Haughan, Alan F.;O’Connell, Catherine;Mead, Tania;McNeil, Hannah;Vann, Julie;Mangette, John;Maillard, Michel;Beaumont, Vahri;Munoz-Sanjuan, Ignacio;Dominguez, Celia. And the article was included in Journal of Medicinal Chemistry in 2013.COA of Formula: C8H8BrN This article mentions the following:

Inhibition of class IIa histone deacetylase (HDAC) enzymes have been suggested as a therapeutic strategy for a number of diseases, including Huntington’s disease. Catalytic-site small mol. inhibitors of the class IIa HDAC4, -5, -7, and -9 were developed (e.g., I). These trisubstituted diarylcyclopropanehydroxamic acids were designed to exploit a lower pocket that is characteristic for the class IIa HDACs, not present in other HDAC classes. Selected inhibitors were cocrystd. with the catalytic domain of human HDAC4. We describe the first HDAC4 catalytic domain crystal structure in a “closed-loop” form, which in our view represents the biol. relevant conformation. We have demonstrated that these mols. can differentiate class IIa HDACs from class I and class IIb subtypes. They exhibited pharmacokinetic properties that should enable the assessment of their therapeutic benefit in both peripheral and CNS disorders. These selective inhibitors provide a means for evaluating potential efficacy in preclin. models in vivo. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-cyclopropylpyridine (cas: 1086381-28-3COA of Formula: C8H8BrN).

4-Bromo-2-cyclopropylpyridine (cas: 1086381-28-3) 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. COA of Formula: C8H8BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Locking PDK1 in DFG-out conformation through 2-oxo-indole containing molecules: Another tools to fight glioblastoma was written by Sestito, Simona;Daniele, Simona;Nesi, Giulia;Zappelli, Elisa;Di Maio, Danilo;Marinelli, Luciana;Digiacomo, Maria;Lapucci, Annalina;Martini, Claudia;Novellino, Ettore;Rapposelli, Simona. And the article was included in European Journal of Medicinal Chemistry in 2016.Safety of 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid This article mentions the following:

The phosphoinositide-dependent kinase-1 (PDK1) is one of the main components of the PI3K/Akt pathway. Also named the “master kinase” of the AGC family, PDK1 plays a critical role in tumorigenesis, by enhancing cell proliferation and inhibiting apoptosis, as well as in cell invasion and metastasis formation. Although there have been done huge efforts in discovering specific compounds targeting PDK1, nowadays no PDK1 inhibitor has yet entered the clinic. With the aim to pick out novel and potent PDK1 inhibitors, herein the authors report the design and synthesis of a new class of mols. obtained by merging the 2-oxo-indole nucleus with the 2-oxo-pyridonyl fragment, two moieties with high affinity for the PDK1 hinge region and its DFG-out binding site, resp. To this purpose, a small series of compounds were synthesized and a tandem application of docking and Mol. Dynamic (MD) was employed to get insight into their mode of binding. The OXID-pyridonyl hybrid, possessing the lower IC₅₀ (IC₅₀ = 112 nM), was also tested against recombinant kinases involved in the PI3K/PDK1/Akt pathway and was subjected to vitro studies to evaluate the cytotoxicity and the inhibition of tumor cell migration. All together the results let us to consider the OXID-pyridonyl hybrid, as a lead compound of a new generation of PDK1 inhibitors and encourage us to further studies in this direction. In the experiment, the researchers used many compounds, for example, 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (cas: 1001413-01-9Safety of 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid).

1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (cas: 1001413-01-9) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. 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 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

New coordination polymers generated from oxadiazole-containing bidentate ligands and Cu-Cu dimetal units was written by Dong, Yu-Bin;Ma, Jian-Ping;Smith, Mark D.;Huang, Ru-Qi;Tang, Bo;Chen, Dezhan;zur Loye, Hans-Conrad. And the article was included in Solid State Sciences in 2002.Related Products of 15420-02-7 This article mentions the following:

Two new coordination polymers that contain di-Cu (Cu₂) units were prepared using Cu(OAc)₂·H₂O in combination with (1,3,4)-oxadiazole organic ligands L₁ and L₂ with dipyridyl substituents in MeOH. The compounds were characterized by single crystal x-ray diffraction, IR spectroscopy, and TGA. The structure of compound 1 (monoclinic, space group C2/c, a 19.9952(14), b 7.5005(5), c 16.0442(11) Å, β 109.000(10)°, Z = 4) features 1-dimensional zigzag chains that are cross-linked into a novel three-dimensional network by weak noncovalvent π-π interactions between the 3-pyridyl rings on the L₁ ligand. Compound 2 (monoclinic, space group C2/c, a 27.428(2), b 13.3833(11), c 8.6339(7) Å, β 103.973(2)°, Z = 4) also features a zigzag chain motif. In the solid state, small and large hexagonal channels are found in 1 and 2, resp. Compounds 1 and 2 are new examples of metal dimer-containing coordination polymers. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Related Products of 15420-02-7).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) 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). Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Related Products of 15420-02-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lead(II) compounds with neutral coordination of semicarbazones: Synthesis and characterization was written by Oliveira Araujo, Vinicius;Antonio Casagrande, Gleison;Tirloni, Barbara;Denise Schwade, Vania. And the article was included in Inorganica Chimica Acta in 2022.Safety of Phenyl(pyridin-2-yl)methanone This article mentions the following:

2-Benzoylpyridine semicarbazide/4-phenylsemicarbazide derived ligands as hydrochloride salts, [H₂L]Cl and [H₂L^Ph]Cl·2H₂O, react with Pb²⁺ ions in aqueous and organic milieus. The compounds [Pb₂(HL)₂Cl₄]·2DMF (1a), [Pb₂(HL)₂Cl₄]·5H₂O (1b), [Pb₂(HL)₂Cl₂(NO₃)₂]·4H₂O (2), [Pb₂(HL)₂(SCN)₄] (3), [Pb₄(HL^Ph)₄Cl₈] (4), [Pb(HL^Ph)₂(NO₃)₂] (5) and [Pb(HL^Ph)₂(SCN)₂] (6) were obtained and characterized by powder x-ray diffraction and by IR and UV-visible spectroscopies. Compounds 1–5 were analyzed by single-crystal x-ray diffraction. Tetrel and hydrogen bonds dominate the solid-state arrangements. The aqueous synthetic approach makes the pre-ligands of this work promising for further studies in aqueous coordination chem. with p-block metal ions. [H₂L]Cl and [H₂L^Ph]Cl·2H₂O are suitable for coordination as neutral HL or HL^Ph species. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Safety of Phenyl(pyridin-2-yl)methanone).

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Basic matrixes for the matrix-assisted laser desorption/ionization mass spectrometry of proteins and oligonucleotides was written by Fitzgerald, Michael C.;Parr, Gary R.;Smith, Lloyd M.. And the article was included in Analytical Chemistry in 1993.Category: pyridine-derivatives This article mentions the following:

In order to examine the importance of pH in the matrix-assisted laser desorption/ionization (MALDI) anal. of proteins and oligonucleotides, 37 highly substituted pyrimidine, pyridine, and benzene derivatives containing basic amino groups were screened as potential matrixes. Several of these compounds were useful for the preparation and anal. of samples under neutral and basic pH conditions. The matrix, 2-amino-4-methyl-5-nitropyridine, gave good results with small proteins (up to ∼12,000 Da). The best results with oligonucleotides were obtained with 2-amino-5-nitropyridine, which was a useful matrix for the anal. of mixed-base oligonucleotides smaller than 20 nucleotides in length and homopolymers of thymidine. In general, oligonucleotide anal. using basic matrixes was found to be subject to similar constraints of size and base composition that hold when acidic matrixes are used. A major advantage of these newly discovered matrix materials over the more commonly used acidic matrixes is that they extend the utility of MALDI to the anal. of acid-sensitive species. In the experiment, the researchers used many compounds, for example, 3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3Category: pyridine-derivatives).

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. 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.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Onium compounds. XVI. Quaternary derivation of pyridyl ethers was written by Renshaw, R. R.;Conn, R. C.. And the article was included in Journal of the American Chemical Society in 1937.Synthetic Route of C11H9NO This article mentions the following:

The following compounds have been prepared for pharmacol. examination The 2-pyridyl ethers were prepared from 2-C₅H₄NBr, PhOH and K₂CO₃ at 200-10° for 3 h. The 4-isomers were obtained by heating 4-pyridylpyridinium dichloride with excess of PhOH and 1.1 mol of its Na salt. 2-PhO, b₁₁ 134-5°, 92% yield; 2-o-cresoxy, b₂₁ 156-8°, 90%; p-isomer, b₂₂ 171.5-2.5°, 92%; m-isomer, b₂₀ 164-6°, 83%; 2-carvacroxy, b₂ 133-4°, 73%; resorcinol di-2-pyridyl ether, b₃ 183-5°, 38%; 2-pyridyl benzyl ether, b₂₀ 162-4°, 65%; 4-BuO, b₂₅ 129-31°, 37%; 4-MeO, b₃₁ 95-6° (picrate, m. 171-2°); 4-PhO, b₂₁ 157-8°; 4-o-, -m- and -p-cresoxy, b₁₉ 161-2°, b₂₂ 166-7°, b₄ 124-6°, resp. The onium derivatives were prepared from the ether and alkyl halide in Et₂O at room or slightly elevated temperature for from 1 to 6 days. Pyridinium iodides.-2-Phenoxymethyl, m. 174-5°, 96% (all m. ps. corrected); 2-phenoxyethyl, m. 150.5-1.5°, 57%; 2-o-cresoxymethyl, m. 186-6.2° (decomposition), 92%; p-isomer, m. 149-50°, 93%; m-isomer, m. 145-6.5°, 90%; 2-o-cresoxyethyl, m. 122-4°, 69%; m-isomer, m. 126-6.5°, 70%; 2-carvacroxymethyl, m. 134-5°, 85%; 3-phenoxymethyl, yellow, m. 82.5-4°, 96%; 3-phenoxyethyl, m. 136-7°, 98%; 4-phenoxymethyl, m. 227.5-8.5°, 68%; 4-phenoxyethyl, m. 110.5-11°, 70%; 4-o-cresoxy, m. 163-4°, 100%; p-isomer, m. 163°, 81%; m-isomer, m. 157-8°, 92%; 4-o-cresoxyethyl, m. 148°, 79%; p-isomer, m. 126-6.5°, 93%; m-isomer, m. 128°, 85%; 4-p-cresoxy-β-phenoxyethyl (as bromide), m. 129-30°, 64%; 4-m-methoxymethyl, m. 145° (decomposition), 100%; 4-butoxymethyl, m. 74-5°, 100%. N-4′-Pyridyl-4-pyridone forms a chloroaurate, yellow, m. 218-19°, and a chloroplatinate, buff, m. above 300°; di-HCl salt, m. 238° (decomposition) methiodide(N-(4′- methylpyridinium iodide)-4-pyridone), yellowish brown, m. 238-8.5°, 95% yield; ethiodide, with 1 mol H₂O, buff m. 134-5°. 3-Phenoxypyridine, b₁₇ 147-9°, results in 27% yield from 3-HOC₅H₄N, 3-KOC₅H₄N and PhBr with Cu bronze at 200° for 6 h., or in 59% yield from 3-IC₅H₄N and PhOK in PhOH with Cu bronze (46% with K₂CO₃). 2-and 4-Phenoxymethylpyridinium iodides are reduced with cleavage of the PhO group, PhOH and N-methylpiperidine being formed. The 3-isomer is readily reduced without the loss of the PhO group (unless in the presence of a large quantity of catalyst); 3-phenoxydimethylpiperidinium iodide, m. 177-8° (corrected). This behavior is general, the stability and aromatic nature of 3-substituted pyridines being quite marked, whereas 2- and 4-pyridyl derivatives are characterized by the lability and often by the anomalous behavior of the substituted groups. 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. 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.Synthetic Route of C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem