Month: October 2022

In 2022,Fan, Jiang-Tao; Fan, Xin-Heng; Gao, Cai-Yan; Wei, Jinchao; Yang, Lian-Ming published an article in Organic Chemistry Frontiers. The title of the article was 《Regioselectively switchable alkyne cyclotrimerization catalyzed by a Ni(II)/bidentate P-ligand/Zn system with ZnI2 as an additive》.Computed Properties of C7H5N The author mentioned the following in the article:

A simple catalytic system of Ni(PPh3)2Cl2/dppb or dppm/Zn can effect an efficient and regioselectively controlled alkyne cyclotrimerization to form 1,2,4- (with no additive) or 1,3,5-regioisomers (with the use of a ZnI2 additive). This protocol features the advantages of facile manipulation, mild conditions, broad substrate scope, high yields, excellent functional-group tolerance and easily controllable regioselectivity, and demonstrates practical potential for the construction of complicated and well-defined poly-substituted benzene derivatives The mechanistic studies were carried out preliminarily. In addition to this study using 4-Ethynylpyridine, there are many other studies that have used 4-Ethynylpyridine(cas: 2510-22-7Computed Properties of C7H5N) was used in this study.

4-Ethynylpyridine(cas: 2510-22-7) 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 C7H5N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Xu, Guozhang; Liu, Zhijie; Wang, Xinkang; Lu, Tianbao; DesJarlais, Renee L.; Thieu, Tho; Zhang, Jing; Devine, Zheng Huang; Du, Fuyong; Li, Qiu; Milligan, Cynthia M.; Shaffer, Paul; Cedervall, Peder E.; Spurlino, John C.; Stratton, Christopher F.; Pietrak, Beth; Szewczuk, Lawrence M.; Wong, Victoria; Steele, Ruth A.; Bruinzeel, Wouter; Chintala, Madhu; Silva, Jose; Gaul, Michael D.; Macielag, Mark J.; Nargund, Ravi published an article in Journal of Medicinal Chemistry. The title of the article was 《Discovery of Potent and Orally Bioavailable Pyridine N-Oxide-Based Factor XIa Inhibitors through Exploiting Nonclassical Interactions》.Reference of 2,5-Dibromopyridine The author mentioned the following in the article:

Herein, activated factor XI (FXIa) inhibitors novel anticoagulants, discovery effort, utilizing nonclassical interactions to improve potency, cellular permeability, and oral bioavailability by enhancing the binding while reducing polar atoms was described. Beginning with literature-inspired pyridine N-oxide-based FXIa inhibitor 1, the imidazole linker was first replaced with a pyrazole moiety to establish a polar C-H···water hydrogen-bonding interaction. Then, structure-based drug design was employed to modify lead mol. I in the P1′ and P2′ regions, with substituents interacting with key residues through various nonclassical interactions. As a result, a potent FXIa inhibitor II (Ki = 0.17 nM) was discovered. This compound demonstrated oral bioavailability in preclin. species (rat 36.4%, dog 80.5%, and monkey 43.0%) and displayed a dose-dependent antithrombotic effect in a rabbit arteriovenous shunt model of thrombosis.2,5-Dibromopyridine(cas: 624-28-2Reference of 2,5-Dibromopyridine) was used in this study.

2,5-Dibromopyridine(cas: 624-28-2) 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. Reference of 2,5-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Hood, Jacob C.; Tshikaya, Yannick; Manz, Aaren R.; LaPorte, Marcus C.; Klumpp, Douglas A. published an article in Journal of Organic Chemistry. The title of the article was 《Double Addition Reactions Involving Vinyl-Substituted N-Heterocycles and Active Methylene Compounds》.Application of 626-05-1 The author mentioned the following in the article:

A series of conjugate addition reactions was performed with vinyl-substituted N-heterocycles with active methylene compounds such as 1,3-dicarbonyl compounds, cyano esters, a cyano sulfone and malonyl nitrile to provide dipyridyl and related heterocyclic products I [R1 = R2 = H, (pyridin-4-yl)ethyl, (pyridin-2-yl)ethyl, (pyrazin-2-yl)ethyl, (quinolin-2-yl)ethyl, (quinoxalin-2-yl)ethyl; n = 0, 1; X = O, CH2, NMe; R1 = H, Me, R2 = H, Ph, 4-(Me)2NC6H4, etc.] in acid-catalyzed conversions. The Michael accepting groups included vinyl-substituted pyridines, quinoline, and pyrazine. Double conjugate addition reactions was accomplished with 2,6-divinylpyridine and related systems. After reading the article, we found that the author used 2,6-Dibromopyridine(cas: 626-05-1Application of 626-05-1)

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. Application of 626-05-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Zhang, Zhen; Li, Jie; Chen, Hao; Huang, Jing; Song, Xiaojuan; Tu, Zheng-Chao; Zhang, Zhang; Peng, Lijie; Zhou, Yang; Ding, Ke published an article in Journal of Medicinal Chemistry. The title of the article was 《Design, Synthesis, and Biological Evaluation of 2-Formyl Tetrahydronaphthyridine Urea Derivatives as New Selective Covalently Reversible FGFR4 Inhibitors》.Reference of 4-Ethynylpyridine The author mentioned the following in the article:

Aberrant FGF19/FGFR4 signaling is an oncogenic driver force for the development of human hepatocellular carcinoma (HCC). A series of 2-formyl tetrahydronaphthyridine urea derivatives I (R = 2-phenylethynyl, 2-(pyridin-2-yl)ethynyl, 2-(3-methoxyphenyl)ethyl, etc.; R1 = F, propan-2-yloxidanyl, cyclopentylaminyl, etc.) and II was designed and synthesized as new covalently reversible inhibitors of FGFR4. The representative compound II (R = 2-(pyridin-3-yl)ethynyl) (III) exhibited an IC50 value of 5.4 nM against FGFR4 and demonstrated extraordinary kinome selectivity. Compound III also exhibited good oral pharmacokinetic properties with an AUC(0-t) value of 38 950.06 h*ng/mL, a T1/2 value of 3.06 h, and an oral bioavailability of 50.97%, at an oral dose of 25 mg/kg in Sprague-Dawley (SD) rats. Furthermore, compound III induced significant tumor regressions in a xenograft mouse model of Hep3B2.1-7 HCC cancer cells without an obvious sign of toxicity upon 30 mg/kg oral administration. Compound III may serve as a promising lead compound for further anticancer drug development. After reading the article, we found that the author used 4-Ethynylpyridine(cas: 2510-22-7Reference of 4-Ethynylpyridine)

4-Ethynylpyridine(cas: 2510-22-7) 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. Reference of 4-Ethynylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Ju, Zhao-Yang; Song, Li-Na; Chong, Ming-Ben; Cheng, Dang-Guo; Hou, Yang; Zhang, Xi-Ming; Zhang, Qing-Hua; Ren, Lan-Hui published an article in Journal of Organic Chemistry. The title of the article was 《Selective Aerobic Oxidation of Csp3-H Bonds Catalyzed by Yeast-Derived Nitrogen, Phosphorus, and Oxygen Codoped Carbon Materials》.COA of Formula: C7H7NO The author mentioned the following in the article:

Nitrogen, phosphorus and oxygen codoped carbon catalysts were successfully synthesized using dried yeast powder as pyrolysis precursor. The yeast-derived heteroatom-doped carbon (yeast@C) catalysts exhibited outstanding performance in the oxidation of Csp3-H bonds to ketones and esters giving excellent products yields (up to 98% yield) without organic solvents at low O2 pressure (0.1 MPa). The catalytic oxidation protocol exhibited broad range of substrates (38 examples) with good functional group tolerance, excellent regioselectivity and synthetic utility. The yeast-derived heteroatom-doped carbon catalysts showed good reusability and stability after recycle six times without any significant loss of activity. Exptl. results and DFT calculations proved the important role of N-oxide (N+-O-) on the surface of yeast@C and a reasonable carbon radical mechanism. In the experiment, the researchers used 4-Acetylpyridine(cas: 1122-54-9COA of Formula: C7H7NO)

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.COA of Formula: C7H7NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Wang, Yu-Zhao; Lin, Wu-Jie; Liu, Hong-Chao; Yu, Wei published an article in Organic Chemistry Frontiers. The title of the article was 《Visible-light-promoted radical amidoarylation of arylacrylamides towards amidated oxindoles》.Product Details of 94928-86-6 The author mentioned the following in the article:

A visible-light-promoted intermol. radical amidation/cyclization of arylacrylamides was realized by using N-aminopyridinium salts as the source of amidyl radicals. The reaction exhibited a broad scope and good functional group tolerance and a variety of amide-tethered-oxindoles were prepared in this way in moderate to good yields. In the experiment, the researchers used many compounds, for example, fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6Product Details of 94928-86-6)

fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. Product Details of 94928-86-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 100-48-1In 2020 ,《Halogen bonding interactions in the XC5H4N···YCF3 (X = CH3, H, Cl, CN, NO2; Y = Cl, Br, I) complexes》 appeared in Journal of Molecular Modeling. The author of the article were Sun, Yuanyuan; Shi, Bo; Zhang, Xueying; Zeng, Yanli. The article conveys some information:

The noncovalent interactions between the σ-hole region outside the halogen atom and the nitrogen atom of pyridine and its para-substituted derivatives are the focus of this work. Based on the analyses of the electrostatic potentials, YCF3 (Y = Cl, Br, I) act as halogen bond donors, XC5H4N (X = CH3, H, Cl, CN, NO2) act as halogen bond acceptors, and the binary halogen-bonded complexes XC5H4N···YCF3 have been designed and investigated by B3LYP-D3/aug-cc-pVDZ calculations together with the aug-cc-pVDZ-PP basis set for iodine. When the halogen bond acceptor remains unchanged, the interactions between C5H5N and YCF3 (Y = Cl, Br, I) increase with the order of Y = Cl, Br, and I. When the halogen donor ICF3 is fixed, the halogen bonding interactions decrease along the sequence of X = CH3, H, Cl, CN, NO2. Therefore, the halogen bond of the CH3C5H4N···ICF3 complex is the strongest. The interactions between Lewis acid YCF3 (Y = Cl, Br, I) and pyridine and para-substituted pyridine are closed-shell and noncovalent interactions. On the one hand, when the halogen bond acceptor XC5H4N is fixed, with the increase of halogen at. number, the strength of halogen bond increases; on the other hand, when the halogen bond donor ICF3 is fixed, as the electron-withdrawing ability of the electron-withdrawing group (X) increases, the halogen bond gradually weakens.4-Cyanopyridine(cas: 100-48-1Application of 100-48-1) was used in this study.

4-Cyanopyridine(cas: 100-48-1) belongs to pyridine. The basicity and metallophilic high donor number of these π-deficient systems has long favored them as ligands in metal catalysis. The last decade saw pyridine assume a stronger role as functional group for directed C–H oxidation/activation.Application of 100-48-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of Pyridin-3-ylboronic acidIn 2022 ,《Facile Synthesis of 2-Methylnicotinonitrile through Degenerate Ring Transformation of Pyridinium Salts》 appeared in Journal of Organic Chemistry. The author of the article were Duan, Xiaoxia; Sun, Rui; Tang, Juan; Li, Shun; Yang, Xiao; Zheng, Xueli; Li, Ruixiang; Chen, Hua; Fu, Haiyan; Yuan, Maolin. The article conveys some information:

Nucleophilic recyclization of pyridinium salts involving a CCN interchange ring transformation for the synthesis of 2-methylnicotinonitrile derivatives was herein developed. 3-Aminocrotononitrile (3-ACN) produced in situ from CH3CN acted as a C-nucleophile, as well as the source of CH3 and CN groups, which was supported by isotope-labeling and control experiments In the experimental materials used by the author, we found Pyridin-3-ylboronic acid(cas: 1692-25-7Reference of Pyridin-3-ylboronic acid)

Pyridin-3-ylboronic acid(cas: 1692-25-7) belongs to pyridine. The basicity and metallophilic high donor number of these π-deficient systems has long favored them as ligands in metal catalysis. The last decade saw pyridine assume a stronger role as functional group for directed C–H oxidation/activation.Reference of Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Formula: C7H6BrNO2In 2016 ,《Discovery of 2-((R)-4-(2-Fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1R,2s,3S,5S,7S)-5-hydroxyadamantan-2-yl)pyrimidine-4-carboxamide (SKI2852): A Highly Potent, Selective, and Orally Bioavailable Inhibitor of 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1)》 was published in Journal of Medicinal Chemistry. The article was written by Ryu, Je Ho; Lee, Jung A.; Kim, Shinae; Shin, Young Ah; Yang, Jewon; Han, Hye Young; Son, Hyun Joo; Kim, Yong Hyuk; Sa, Joon Ho; Kim, Jae-Sun; Lee, Jungeun; Lee, Jeeyeon; Park, Hyeung-geun. The article contains the following contents:

A series of picolinamide- and pyrimidine-4-carboxamide-based inhibitors of 11β-hydroxysteroid dehydrogenase type 1 was synthesized and evaluated to optimize the lead compound The combination of the replacement of a pyridine ring of the lead compd with a pyrimidine ring and the introduction of an addnl. fluorine substituent at the 2-position of the Ph ring resulted in the discovery of a potent, selective, and orally bioavailable inhibitor, SKI2852, which demonstrated no CYP and PXR liabilities, excellent PK profiles across species, and highly potent and sustainable PD activity. Repeated oral administration of SKI2852 significantly reduced blood glucose and HbA1c levels and improved the lipid profiles in ob/ob mice. Moreover, the HbA1c-lowering effect of metformin was synergistically enhanced in combination with SKI2852. In the part of experimental materials, we found many familiar compounds, such as Methyl 5-bromopicolinate(cas: 29682-15-3Formula: C7H6BrNO2)

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Formula: C7H6BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of C33H24IrN3In 2021 ,《Photocatalytic Radical Ortho-Dearomative Cyclization: Access to Spiro[4.5]deca-1,7,9-trien-6-ones》 was published in Journal of Organic Chemistry. The article was written by Dong, Wuheng; Yuan, Yao; Liang, Caiyun; Wu, Feng; Zhang, Siyuan; Xie, Xiaomin; Zhang, Zhaoguo. The article contains the following contents:

A highly efficient ortho-dearomative cyclization reaction between alkynes and 2-bromo-2-(2-methoxybenzyl)malonates via visible light-induced photoredox catalysis has been reported. In the presence of 1 mol% fac-Ir(ppy)3, a variety of spiro[4.5]deca-1,7,9-trien-6-ones, e.g., I, was obtained in moderate to excellent yields under mild conditions. Under the optimized reaction conditions, a sample reaction of 3 mmol scale proceeded smoothly to give the desired products in 84% yield with a low catalyst loading of 0.1 mol%. In the experiment, the researchers used fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6Electric Literature of C33H24IrN3)

fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Electric Literature of C33H24IrN3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem