Month: October 2022

《Metal-Free, Redox-Neutral, Site-Selective Access to Heteroarylamine via Direct Radical-Radical Cross-Coupling Powered by Visible Light Photocatalysis》 was written by Zhou, Chao; Lei, Tao; Wei, Xiang-Zhu; Ye, Chen; Liu, Zan; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu. Safety of 4-Cyanopyridine And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

Transition-metal-catalyzed C-N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chems. Reported herein is an alternative access to heteroarylamine via radical-radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C-N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C-N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings. In the experiment, the researchers used many compounds, for example, 4-Cyanopyridine(cas: 100-48-1Safety of 4-Cyanopyridine)

4-Cyanopyridine(cas: 100-48-1) belongs to pyridine. Pyridines form stable salts with strong acids. Pyridine itself is often used to neutralize acid formed in a reaction and as a basic solvent. Safety of 4-Cyanopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Design, synthesis and anticancer properties of isocombretapyridines as potent colchicine binding site inhibitors》 was written by Shuai, Wen; Li, Xinnan; Li, Wenlong; Xu, Feijie; Lu, Lixue; Yao, Hong; Yang, Limei; Zhu, Huajian; Xu, Shengtao; Zhu, Zheying; Xu, Jinyi. HPLC of Formula: 1122-54-9 And the article was included in European Journal of Medicinal Chemistry in 2020. The article conveys some information:

A series of novel isocombretapyridines were designed and synthesized based on a lead compound isocombretastatin A-4 (isoCA-4) by replacing 3,4,5-trimethoxylphenyl with substituent pyridine nucleus. The MTT assay results showed that compound I possessed the most potent activities against all tested cell lines with IC50 values at nanomolar concentration ranges. Moreover, I inhibited tubulin polymerization at a micromolar level and also displayed potent anti-vascular activity in vitro. Further mechanistic studies were conducted to demonstrate that compound I could bind to the colchicine site of tubulin,and disrupte the cell microtubule networks, induce G2/M phase arrest, promote apoptosis and depolarize mitochondria of K562 cells in a dose-dependent manner. Notably, I exhibited more potent tumor growth inhibition activity with 68.7% tumor growth inhibition than that of isoCA-4 in H22 allograft mouse model without apparent toxicity. The present results suggested that compound I may serve as a promising potent microtubule-destabilizing agent candidate for the development of therapeutics to treat cancer. In the experiment, the researchers used 4-Acetylpyridine(cas: 1122-54-9HPLC of Formula: 1122-54-9)

4-Acetylpyridine(cas: 1122-54-9) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.HPLC of Formula: 1122-54-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Favalli, Nicholas; Bassi, Gabriele; Bianchi, Davide; Scheuermann, Jorg; Neri, Dario published their research in Bioorganic & Medicinal Chemistry in 2021. The article was titled 《Large screening of DNA-compatible reaction conditions for Suzuki and Sonogashira cross-coupling reactions and for reverse amide bond formation》.HPLC of Formula: 2510-22-7 The article contains the following contents:

Progress in DNA-encoded chem. library synthesis and screening crucially relies on the availability of DNA-compatible reactions, which proceed with high yields and excellent purity for a large number of possible building blocks. In the past, exptl. conditions have been presented for the execution of Suzuki and Sonogashira cross-coupling reactions on-DNA. In this article, our aim was to optimize Suzuki and Sonogashira reactions, comparing our results to previously published procedures. We have tested the performance of improved conditions using 606 building blocks (including boronic acids, pinacol boranes and terminal alkynes), achieving >70% conversion for 84% of the tested mols. Moreover, we describe efficient exptl. conditions for the on-DNA synthesis of amide bonds, starting from DNA derivatives carrying a carboxylic acid moiety and 300 primary, secondary and aromatic amines, as amide bonds are frequently found in DNA-encoded chem. libraries thanks to their excellent DNA compatibility.4-Ethynylpyridine(cas: 2510-22-7HPLC of Formula: 2510-22-7) was used in this study.

4-Ethynylpyridine(cas: 2510-22-7) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.HPLC of Formula: 2510-22-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Bandarage, Upul K.; Aronov, Alex M.; Cao, Jingrong; Come, Jon H.; Cottrell, Kevin M.; Davies, Robert J.; Giroux, Simon; Jacobs, Marc; Mahajan, Sudipta; Messersmith, David; Moody, Cameron S.; Swett, Rebecca; Xu, Jinwang published their research in ACS Medicinal Chemistry Letters in 2021. The article was titled 《Discovery of a Novel Series of Potent and Selective Alkynylthiazole-Derived PI3Kγ Inhibitors》.Electric Literature of C7H5N The article contains the following contents:

Phosphoinositide 3-kinases (PI3Ks) are a family of enzymes that control a wide variety of cellular functions such as cell growth, proliferation, differentiation, motility, survival, and intracellular trafficking. PI3Kγ plays a critical role in mediating leukocyte chemotaxis as well as mast cell degranulation, making it a potentially interesting target for autoimmune and inflammatory diseases. We previously disclosed a novel series of PI3Kγ inhibitors derived from a benzothiazole core. The truncation of the benzothiazole core led to the discovery of a structurally diverse alkynyl thiazole series which displayed high PI3Kγ potency and subtype selectivity. Further medicinal chem. optimization of the alkynyl thiazole series led to identification of compounds such as 14 and 32, highly potent, subtype selective, and CNS penetrant PI3Kγ inhibitors. Compound 14 showed robust inhibition of PI3Kγ mediated neutrophil migration in vivo. In the part of experimental materials, we found many familiar compounds, such as 4-Ethynylpyridine(cas: 2510-22-7Electric Literature of C7H5N)

4-Ethynylpyridine(cas: 2510-22-7) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.Electric Literature of C7H5N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Rani, Chekuri Sharmila; Reddy, Alugubelli Gopi; Susithra, E.; Mak, Kit-Kay; Pichika, Mallikarjuna Rao; Reddymasu, Sreenivasulu; Rao, Mandava Venkata Basaveswara published their research in Medicinal Chemistry Research in 2021. The article was titled 《Synthesis and anticancer evaluation of amide derivatives of imidazo-pyridines》.Computed Properties of C5H3Br2N The article contains the following contents:

Abstract: A novel series of amide functionalized imidazo[1,2-a]pyridine (14a-14j) derivatives were synthesized and screened for their anticancer activities against breast (MCF-7 and MDA-MB-231), lung (A549), and prostate (DU-145) cancer cell lines using MTT assay with etoposide as the standard reference drug. Among them, compound 14 showed highest potency in anticancer activities against MCF-7, MDA-MB-231, A549, and DU-145 cell lines with IC50 values of 0.021 ± 0.0012μM, 0.95 ± 0.039μM, 0.091 ± 0.0053μM, and 0.24 ± 0.032μM, resp. In the part of experimental materials, we found many familiar compounds, such as 2,5-Dibromopyridine(cas: 624-28-2Computed Properties of C5H3Br2N)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine’s structure is isoelectronic with that of benzene, but its properties are quite different. Pyridine is completely miscible with water, whereas benzene is only slightly soluble. Like all hydrocarbons, benzene is neutral (in the acid–base sense), but because of its nitrogen atom, pyridine is a weak base.Computed Properties of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Dhau, Jaspreet S.; Singh, Avtar; Brandao, Paula; Felix, Vitor published their research in Inorganic Chemistry Communications in 2021. The article was titled 《Synthesis, characterization, X-ray crystal structure and antibacterial activity of bis[3-(4-chloro-N,N-diethylpyridine-2-carboxamide)] diselenide》.Formula: C6H5NO2 The article contains the following contents:

An efficient methodol. for the synthesis of bis[3-(4-chloro-N,N-diethylpyridine-2-carboxamide)] diselenide has been successfully achieved through ring lithiation using 2.2 equiv of lithium diisopropylamide (LDA) in THF. The hitherto unknown compound has been fully characterized by spectroscopic techniques NMR (1H and 13C), Mass spectrometry and elemental anal. The crystal structure of bis[3-(4-chloro-N,N-diethylpyridine-2-carboxamide)] diselenide has been determined by single crystal x-ray diffraction. The diselenide crystallizes in the monoclinic system (C2/c) with torsional angle of the selenium atoms attached to pyridyl rings (-C1-Se-Se-C1-) is -77.5(1). Bis[3-(4-chloro-N,N-diethylpyridine-2-carboxamide)] diselenide was found antibacterial active and results were compared with the most studied pyridylselenium compound (2,2′-dipyridyl diselenide) and standard drug Ampicillin. After reading the article, we found that the author used Picolinic acid(cas: 98-98-6Formula: C6H5NO2)

Picolinic acid(cas: 98-98-6) is used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes.Formula: C6H5NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Mukherjee, Debojyoti; Manna, Rabindra Nath; Saha, Paramita; Mandal, Ujjwal; Mitra, Mainak published their research in Journal of Molecular Structure in 2021. The article was titled 《Electronic and molecular characterization of an air-stable Cr(II) complex containing azo-anion-radicals》.Recommanded Product: 141-86-6 The article contains the following contents:

A new mononuclear homoleptic chromium complex has been synthesized by reaction of one equivalent of Cr(CO)6 with two equivalent of the azoarom. pincer ligand namely 2,6-bis[(4-methylphenyl)azo]pyridine [LMe] in n-octane under reflux condition. The complex has been fully characterized by ESI-MS, 1H-NMR, FT-IR and UV/Vis spectroscopy. The X-ray structure of the complex reveals that the Cr-metal is coordinated to the central pyridine N-atom and two azo N-atoms of each tridentate pincer ligand in an octahedral environment. The 1H-NMR spectrum of the complex is indicative of diamagnetic ground state. The elongation of N-N bond lengths [d(N-N)av = 1.3275 Å] in the complex is consistent with the presence of azo-anion-radical character in the ligand. Since 2,6-bis(phenylazo)pyridine and its 4-Me-derivative are redox non-innocence in nature and therefore can coordinate to the chromium metal center as neutral (L0) or as mono-anionic mono-radical (L·)1- or as di-anionic di-radical (L··)2- or even as tri-anionic mono-radical (L·)3- resulting an ambiguity on the true oxidation state of the metal center. Thus the present work nicely elaborates the importance of suitably designed bis-azopyridine containing pincer ligand in accessing an air-stable Cr(II) complex starting with low-valent metal carbonyl precursor via electron transfer from the metal center to the highly π-acidic ligand leading to stable azo-anion-radicals. The stability of azo-anion-radical bound Cr(II) complex has been investigated by DFT calculations The experimental process involved the reaction of 2,6-Diaminopyridine(cas: 141-86-6Recommanded Product: 141-86-6)

2,6-Diaminopyridine(cas: 141-86-6) belongs to pyridine. Pyridine and its simple derivatives are stable and relatively unreactive liquids, with strong penetrating odours that are unpleasant.Recommanded Product: 141-86-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

McConnell, Danielle L.; Blades, Alisha M.; Rodrigues, Danielle Gomes; Keyes, Phoebe V.; Sonberg, Justin C.; Anthony, Caitlin E.; Rachad, Sofia; Simone, Olivia M.; Sullivan, Caroline F.; Shapiro, Jonathan D.; Williams, Christopher C.; Schafer, Benjamin C.; Glanzer, Amy M.; Hutchinson, Holly L.; Thayaparan, Ashley B.; Krevlin, Zoe A.; Bote, Isabella C.; Haffary, Yasin A.; Bhandari, Sambat; Goodman, Jack A.; Majireck, Max M. published an article in 2021. The article was titled 《Synthesis of Bench-Stable N-Quaternized Ketene N,O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis》, and you may find the article in Journal of Organic Chemistry.Category: pyridine-derivatives The information in the text is summarized as follows:

In this report, a general synthetic approach to a variety of bench-stable N-quaternized ketene N,O-acetals I (R = H, 2-Ph, 4-Me, 2,6-Cl2, etc.; X = OTf, NTf2) via treatment of pyridine II or aniline bases with acetylenic ethers R1CC (R1 = OEt, 4-methoxyphenyl) and an appropriate Bronsted or Lewis acid (triflic acid, triflimide, or scandium(III) triflate) have been described. The resulting pyridinium I and anilinium salts C6H5N+((CH3)CH2)C(=CH2)R1 X- can be used as reagents or synthetic intermediates in multiple reaction types. For example, N-(1-ethoxyvinyl)pyridinium or anilinium salts can thermally release highly reactive O-Et ketenium ions for use in acid catalyst-free electrophilic aromatic substitutions. N-(1-ethoxyvinyl)-2-halopyridinium salts I (R = 2-Cl, 2-Br) can be employed in peptide couplings as a derivative of Mukaiyama reagent (2-chloro-1-methylpyridinium iodide) or react with phenylmethanamine in nucleophilic aromatic substitutions under mild conditions. These preliminary reactions illustrate the broad potential of these currently understudied compounds in organic synthesis. In the experiment, the researchers used many compounds, for example, 2,6-Dibromopyridine(cas: 626-05-1Category: pyridine-derivatives)

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Liu, Wenwu; Liu, Xin; Tian, Liting; Gao, Yaping; Liu, Wenjie; Chen, Huanhua; Jiang, Xiaowen; Xu, Zihua; Ding, Huaiwei; Zhao, Qingchun published an article in 2021. The article was titled 《Design, synthesis and biological evaluation of harmine derivatives as potent GSK-3β/DYRK1A dual inhibitors for the treatment of Alzheimer’s disease》, and you may find the article in European Journal of Medicinal Chemistry.HPLC of Formula: 1692-25-7 The information in the text is summarized as follows:

Alzheimer’s disease (AD) is a chronic and progressive neurodegenerative disease, characterized by irreversible cognitive impairment, memory loss and behavioral disturbances, ultimately leading to death. Glycogen synthase kinase 3β (GSK-3β) and dual-specificity tyrosine phosphorylation regulated kinase1A (DYRK1A) have gained a lot of attention for its role in tau pathol. To search for potential dual GSK-3β/DYRK1A inhibitors, we focused on harmine, a natural β-carboline alkaloid, which has been extensively studied for its various biol. effects on the prevention of AD. In this study, a new series of harmine derivatives were designed, synthesized and evaluated as dual GSK-3β/DYRK1A inhibitors for their multiple biol. activities. The in vitro results indicated that most of them displayed promising activity against GSK-3β and DYRK1A. Among them, compound ZDWX-25 (I) showed potent inhibitory effects on GSK-3β and DYRK1A with IC50 values of 71 and 103 nM, resp. Mol. modeling and kinetic studies verified that ZDWX-25 could interact with the ATP binding pocket of GSK-3β and DYRK1A. Western blot anal. revealed that ZDWX-25 inhibited hyperphosphorylation of tau protein in okadaic acid (OKA)-induced SH-SY5Y cells. In addition, ZDWX-25 showed good blood-brain barrier penetrability in vitro. More importantly, ZDWX-25 could ameliorate the impaired learning and memory in APP/PS1/Tau transgenic mice. These results indicated that the harmine-based compounds could be served as promising dual-targeted candidates for AD. In the experiment, the researchers used Pyridin-3-ylboronic acid(cas: 1692-25-7HPLC of Formula: 1692-25-7)

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. Pyridines form stable salts with strong acids. Pyridine itself is often used to neutralize acid formed in a reaction and as a basic solvent. HPLC of Formula: 1692-25-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Xu, Mizhi; Paul, McKinley K.; Bullard, Krista K.; DuPre, Christopher; Gutekunst, Will R. published an article in 2021. The article was titled 《Modulating Twisted Amide Geometry and Reactivity Through Remote Substituent Effects》, and you may find the article in Journal of the American Chemical Society.SDS of cas: 1692-25-7 The information in the text is summarized as follows:

The unusual reactivity of twisted amides has long been associated with the degree of amide distortion, though classical bridged bicyclic amides offer limited methods to further modify these parameters. Here, we report that the geometry and reactivity of a single twisted amide scaffold can be significantly modulated through remote substituent effects. Guided by calculated ground state geometries, a library of twisted amide derivatives was efficiently prepared through a divergent synthetic strategy. Kinetic and mechanistic investigations of these amides in the alkylation/halide-rebound ring-opening reaction with alkyl halides show a strong pos. correlation between the electron donating ability of the substituent and distortion of the amide bond, leading to rates of nucleophilic substitution spanning nearly 2 orders of magnitude. The rate limiting step of the cascade sequence is found to be dependent on the nature of the substituent, and addnl. studies highlight the role of solvent polarity and halide ion on reaction pathway and efficiency. The experimental part of the paper was very detailed, including the reaction process of Pyridin-3-ylboronic acid(cas: 1692-25-7SDS of cas: 1692-25-7)

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. When pyridine is adsorbed on oxide surfaces or in porous materials, the following species are commonly observed: (i) pyridine coordinated to Lewis acid sites, (ii) pyridine H-bonded to weakly acidic hydroxyls, and (iii) protonated pyridine. At high coverage, physisorbed pyridine and protonated dimers can also be observed.SDS of cas: 1692-25-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem