Pyridine-derivatives

Application In Synthesis of Bis(pyridin-2-ylmethyl)amineIn 2021 ,《Electrochemical Sensing of Adenosin Triphosphate by Specific Binding to Dipicolylamine Group in Cyclodextrin Supramolecular Complex》 was published in ACS Applied Bio Materials. The article was written by Casulli, Maria Antonietta; Taurino, Irene; Hashimoto, Takeshi; Carrara, Sandro; Hayashita, Takashi. The article contains the following contents:

Electrochem. detection based on cyclodextrin supramol. complexes is founded on the competitive binding between electroactive probes and target mols. This limits their versatility to be used for sensing a broad range of metabolites. In this work, we demonstrate the significant role of zinc ions as well as of β-cyclodextrins modified with dipicolylamine and of a phenylboronic acid-modified ferrocene probe to address a selective electrochem. detection of ATP (ATP). Our findings will definitively have an impact in oncol. point-of-care systems, since a high level of extracellular ATP reveals the inflammatory response due to chemotherapeutic treatments. The experimental part of the paper was very detailed, including the reaction process of Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0Application In Synthesis of Bis(pyridin-2-ylmethyl)amine)

Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0) is a secondary amine with two picolyl substituents. The compound is a tridentate ligand in coordination chemistry and commonly used to produce Zn-based chemosensors/probes, such as Zinpry.Application In Synthesis of Bis(pyridin-2-ylmethyl)amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of C5H6BNO2In 2020 ,《Organoboron-Functionalization Enables the Hierarchical Assembly of Giant Polyoxometalate Nanocapsules》 was published in Angewandte Chemie, International Edition. The article was written by Li, Shujun; Zhou, Yanfang; Ma, Nana; Zhang, Jie; Zheng, Zhiping; Streb, Carsten; Chen, Xuenian. The article contains the following contents:

The aggregation of mol. metal oxides into larger superstructures can bridge the gap between mol. compounds and solid-state materials. Here, we report that functionalization of polyoxotungstates with organo-boron substituents leads to giant polyoxometalate-based nanocapsules with dimensions of up to 4 nm. A “”lock and key”” mechanism enables the site-specific anchoring of aromatic organo-boronic acids to metal-functionalized Dawson anions [M3P2W15O62]9- (M = TaV or NbV), resulting in unique nanocapsules containing up to twelve POM units. Exptl. and theor. studies provide initial insights into the role of the organo-boron moieties and the metal-functionalized POMs for the assembly of the giant aggregates. The study therefore lays the foundations for the design of organo-POM-based functional nanostructures. In the experiment, the researchers used Pyridin-3-ylboronic acid(cas: 1692-25-7Electric Literature of C5H6BNO2)

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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 C5H6BNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of C6H7Br2NIn 2018 ,《Catalytic Synthesis of Indolines by Hydrogen Atom Transfer to Cobalt(III)-Carbene Radicals》 was published in Chemistry – A European Journal. The article was written by Karns, Alexander S.; Goswami, Monalisa; de Bruin, Bas. The article contains the following contents:

A new method was reported for the synthesis of tert-butyl-2-arylindoline-1-carboxylates such as I [R = Ph, 4-MeOC6H4, 2-pyridyl, etc.; R1 = H, 4-Me, 5-MeO, 5-CF3] from ring-closing reaction of o-aminoarylidine-N-tosylhydrazones II proceeded through cobalt(III)-carbene radical intermediate via rapid intramol. 1,5-hydrogen atom transfer (1,5-HAT). This methodol. employed the use of inexpensive com. available reagents and allowed the transformation of easily derivatized benzaldehyde-derived precursors to functionalized indoline products via formation of compounds II. This transformation was the first reported example of the synthesis of nitrogen-containing heterocycles from cobalt(III)-carbene radical precursors. Computational investigations using d. functional theory identified remarkably low barriers for 1,5-HAT and subsequent radical rebound displacement, hence provided support for the proposed mechanism. Furthermore, the steric and electronic effects of substituents on aniline ring and on nitrogen atom were evaluated and highlighted the importance of adequate resonance stabilization of radical intermediates to the success of this transformation. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Synthetic Route of C6H7Br2N)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) 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. Synthetic Route of C6H7Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Name: 2-(2-Hydroxyethyl)pyridineIn 2018 ,《Anion-Radical Salts of 7,7,8,8-Tetracyanoquinodimethane with Cations in the Basis of Alkylolpyridines》 was published in Russian Journal of General Chemistry. The article was written by Starodub, T. N.. The article contains the following contents:

Anion-radical salts of 7,7,8,8-tetracyanoquinodimethane with cations on the basis of methylol- and ethylolpyridines, N-methyl- and N-Et alkylolpyridines, were synthesized. Their composition is determined by the method of electronic spectroscopy, and the thermal stability is studied. The nature of the salts is investigated by the method of IR spectroscopy: it is shown that the conducting properties depend both on the nature of the alkyl group and on the position of the alkylol substituent. The presence of hydroxy groups in the conducting anion-radical salts allow their application as electronic organic materials for the design of conducting film coatings. The experimental part of the paper was very detailed, including the reaction process of 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Name: 2-(2-Hydroxyethyl)pyridine)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) 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. Name: 2-(2-Hydroxyethyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Name: Pyridin-3-ylboronic acidIn 2020 ,《Novel, Potent, and Druglike Tetrahydroquinazoline Inhibitor That Is Highly Selective for Human Topoisomerase II α over β》 was published in Journal of Medicinal Chemistry. The article was written by Ortega, Jose Antonio; Arencibia, Jose M.; Minniti, Elirosa; Byl, Jo Ann W.; Franco-Ulloa, Sebastian; Borgogno, Marco; Genna, Vito; Summa, Maria; Bertozzi, Sine Mandrup; Bertorelli, Rosalia; Armirotti, Andrea; Minarini, Anna; Sissi, Claudia; Osheroff, Neil; De Vivo, Marco. The article contains the following contents:

We disclose a novel class of 6-amino-tetrahydroquinazoline derivatives that inhibit human topoisomerase II (topoII), a validated target of anticancer drugs. In contrast to topoII-targeted drugs currently in clin. use, these compounds do not act as topoII poisons that enhance enzyme-mediated DNA cleavage, a mechanism that is linked to the development of secondary leukemias. Instead, these tetrahydroquinazolines block the topoII function with no evidence of DNA intercalation. We identified a potent lead compound [compound I (ARN-21934) IC50 = 2μM for inhibition of DNA relaxation, as compared to an IC50 = 120μM for the anticancer drug etoposide] with excellent metabolic stability and solubility This new compound also shows ∼100-fold selectivity for topoIIα over topoβ, a broad antiproliferative activity toward cultured human cancer cells, a favorable in vivo pharmacokinetic profile, and the ability to penetrate the blood-brain barrier. Thus, ARN-21934 is a highly promising lead for the development of novel and potentially safer topoII-targeted anticancer drugs. The experimental part of the paper was very detailed, including the reaction process of Pyridin-3-ylboronic acid(cas: 1692-25-7Name: Pyridin-3-ylboronic acid)

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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. Name: Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3-Nitroisonicotinic acidOn September 30, 1991 ,《Proton, carbon-13 and oxygen-17 NMR study of substituted nitropyridines》 was published in Magnetic Resonance in Chemistry. The article was written by Kolehmainen, Erkki; Laihia, Katri; Rasala, Danuta; Gawinecki, Ryszard. The article contains the following contents:

1H, 13C and 17O NMR spectra for 22 substituted nitropyridines were measured and their 1H NMR spectra were analyzed. The most significant variations in the NMR parameters are found for isomeric hydroxy derivatives, owing to the possibility of keto-enol tautomerism. The prevalence of the keto form is observed in 2- and 4-hydroxy derivatives, while the 3-hydroxy derivative exists in its enol form. Among the three nuclei studied, 17O seems to be the best nucleus for probing the keto-enol tautomerism. No correlation is observed between the torsion angle of the nitro group and its 17O NMR chem. shift. Mol. mechanics calculations were performed to clarify the torsional energetics of the nitro group and the preferences for keto-enol tautomerism. In addition to this study using 3-Nitroisonicotinic acid, there are many other studies that have used 3-Nitroisonicotinic acid(cas: 59290-82-3Reference of 3-Nitroisonicotinic acid) was used in this study.

3-Nitroisonicotinic acid(cas: 59290-82-3) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Reference of 3-Nitroisonicotinic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Bernard-Gauthier, Vadim; Aliaga, Arturo; Aliaga, Antonio; Boudjemeline, Mehdi; Hopewell, Robert; Kostikov, Alexey; Rosa-Neto, Pedro; Thiel, Alexander; Schirrmacher, Ralf published an article on February 18 ,2015. The article was titled 《Syntheses and Evaluation of Carbon-11- and Fluorine-18-Radiolabeled pan-Tropomyosin Receptor Kinase (Trk) Inhibitors: Exploration of the 4-Aza-2-oxindole Scaffold as Trk PET Imaging Agents》, and you may find the article in ACS Chemical Neuroscience.Synthetic Route of C9H12N2O2 The information in the text is summarized as follows:

Tropomyosin receptor kinases (TrkA/B/C) are critically involved in the development of the nervous system, in neurol. disorders as well as in multiple neoplasms of both neural and non-neural origins. The development of Trk radiopharmaceuticals would offer unique opportunities toward a more complete understanding of this emerging therapeutic target. To that end, we first developed [11C]GW441756 ([11C]9), a high affinity photoisomerizable pan-Trk inhibitor, as a lead radiotracer for our positron emission tomog. (PET) program. Efficient carbon-11 radiolabeling afforded [11C]9 in high radiochem. yields (isolated RCY, 25.9% ± 5.7%). In vitro autoradiog. studies in rat brain and TrkB-expressing human neuroblastoma cryosections confirmed that [11C]9 specifically binds to Trk receptors in vitro. MicroPET studies revealed that binding of [11C]9 in the rodent brain was mostly nonspecific despite initial high brain uptake (SUVmax = 2.0). Modeling studies of the 4-aza-2-oxindole scaffold led to the successful identification of a small series of high affinity fluorinated and methoxy derivatized pan-Trk inhibitors based on our lead compound 9. Out of this series, the fluorinated compound 10 was selected for initial evaluation and radiolabeled with fluorine-18 (isolated RCY, 2.5% ± 0.6%). Compound [18F]10 demonstrated excellent Trk selectivity in a panel of cancer relevant kinase targets and a promising in vitro profile in tumors and brain sections but high oxidative metabolic susceptibility leading to nonspecific brain distribution in vivo. The information gained in this study will guide further exploration of the 4-aza-2-oxindole scaffold as a lead for Trk PET ligand development.Ethyl 2-(3-aminopyridin-2-yl)acetate(cas: 295327-27-4Synthetic Route of C9H12N2O2) was used in this study.

Ethyl 2-(3-aminopyridin-2-yl)acetate(cas: 295327-27-4) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Synthetic Route of C9H12N2O2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Fraser, Cassandra L.; Anastasi, Natia R.; Lamba, Jaydeep J. S. published their research in Journal of Organic Chemistry on December 26 ,1997. The article was titled 《Synthesis of Halomethyl and Other Bipyridine Derivatives by Reaction of 4,4′-Bis[(trimethylsilyl)methyl]-2,2′-bipyridine with Electrophiles in the Presence of Fluoride Ion》.Synthetic Route of C12H10Cl2N2 The article contains the following contents:

This report describes a new, high yield route to bipyridine derivatives via a trimethylsilyl (TMS) intermediate. 4,4′-Dimethyl-2,2′-bpy was reacted with lithium diisopropylamide, and the dianion thus formed was trapped with TMSCl to generate 4,4′-bis[(trimethylsilyl)methyl]-2,2′-bpy. The TMS group was removed using dry F- sources (TBAF/SiO2 in THF or CsF in DMF) in the presence of BrF2CCF2Br or Cl3CCCl3 to produce the bromide or chloride analogs of 4,4′-bis(halomethyl)-2,2′-bipyridine, resp. The CsF/DMF methodol. extends to other electrophiles, including benzaldehyde to give 4,4′-bis(2-hydroxy-2-phenethyl)-2,2′-bpy as well as to alkyl halides. Benzyl Br, dodecyl Br, and α-chloroacetonitrile gave mixtures of di- and monoalkylated products along with the diprotonated product, 4,4′-dimethyl-2,2′-bpy. In the experiment, the researchers used 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Synthetic Route of C12H10Cl2N2)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) 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. Synthetic Route of C12H10Cl2N2 Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Miller, William H.; Seefeld, Mark A.; Newlander, Kenneth A.; Uzinskas, Irene N.; Burgess, Walter J.; Heerding, Dirk A.; Yuan, Catherine C. K.; Head, Martha S.; Payne, David J.; Rittenhouse, Stephen F.; Moore, Terrance D.; Pearson, Stewart C.; Berry, Valerie; DeWolf, Walter E. Jr.; Keller, Paul M.; Polizzi, Brian J.; Qiu, Xiayang; Janson, Cheryl A.; Huffman, William F. published an article in Journal of Medicinal Chemistry. The title of the article was 《Discovery of Aminopyridine-Based Inhibitors of Bacterial Enoyl-ACP Reductase (FabI)》.Name: 3-(6-Aminopyridin-3-yl)propanoic acid The author mentioned the following in the article:

Bacterial enoyl-ACP reductase (FabI) catalyzes the final step in each cycle of bacterial fatty acid biosynthesis and is an attractive target for the development of new antibacterial agents. Our efforts to identify potent, selective FabI inhibitors began with screening of the GlaxoSmithKline proprietary compound collection, which identified several small-mol. inhibitors of Staphylococcus aureus FabI. Through a combination of iterative medicinal chem. and X-ray crystal structure based design, one of these leads was developed into the novel aminopyridine derivative I, a low micromolar inhibitor of FabI from S. aureus (IC50 = 2.4 μM) and Haemophilus influenzae (IC50 = 4.2 μM). Compound I has good in vitro antibacterial activity against several organisms, including S. aureus (MIC = 0.5 μg/mL), and is effective in vivo in a S. aureus groin abscess infection model in rats. Through FabI overexpressor and macromol. synthesis studies, the mode of action of I has been confirmed to be inhibition of fatty acid biosynthesis via inhibition of FabI. Taken together, these results support FabI as a valid antibacterial target and demonstrate the potential of small-mol. FabI inhibitors for the treatment of bacterial infections.3-(6-Aminopyridin-3-yl)propanoic acid(cas: 446263-96-3Name: 3-(6-Aminopyridin-3-yl)propanoic acid) was used in this study.

3-(6-Aminopyridin-3-yl)propanoic acid(cas: 446263-96-3) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Name: 3-(6-Aminopyridin-3-yl)propanoic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ni, Ming Hong; Esposito, Emiliano; Castorina, Massimo; Dal Pozzo, Alma published an article in Letters in Drug Design & Discovery. The title of the article was 《Novel RGD peptidomimetics embedding 1,2,3-triazole as central scaffold; synthesis and αvβ3 integrin affinity》.HPLC of Formula: 1094679-27-2 The author mentioned the following in the article:

Ten new RGD (Arginine-Glycine-Aspartic acid) peptidomimetics have been synthesized and screened for their affinity to αvβ3 integrin receptor. Arginine and Aspartic acid mimetic subunits were connected through 1,2,3-triazole as central scaffold by click chem., affording the final products with good yields. Among them, compounds 3f-j exhibited high affinity to the receptor, with IC50 in the low nanomolar range, comparable to that of the reference compound Cilengitide. The experimental process involved the reaction of 4-Ethynylpyridin-2-amine(cas: 1094679-27-2HPLC of Formula: 1094679-27-2)

4-Ethynylpyridin-2-amine(cas: 1094679-27-2) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.HPLC of Formula: 1094679-27-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem