Category: pyridine-derivatives

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

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

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

Recommanded Product: 1122-54-9In 2022 ,《Alkyl/Glycosyl Sulfoxides as Radical Precursors and Their Use in the Synthesis of Pyridine Derivatives》 appeared in Angewandte Chemie, International Edition. The author of the article were Xie, Demeng; Wang, Yingwei; Zhang, Xia; Fu, Zhengyan; Niu, Dawen. The article conveys some information:

Here the use of simple and readily available alkyl sulfoxides as precursors to radicals and their application in the preparation of pyridine derivatives are reported. It was shown that alkyl sulfoxides, N-methoxy pyridinium salts and fluoride anions form electron donor-acceptor (EDA) complexes in solution, which, upon visible light irradiation, undergo a radical chain process to afford various pyridine derivatives smoothly. This reaction displays broad scope with respect to both sulfoxides and N-methoxy pyridinium salts. The synthetic versatility of sulfoxides as a handle in chem. adds to their power as radical precursors. Glycosyl sulfoxides are converted to the corresponding pyridyl C-glycosides with high stereoselectivities. Computational and exptl. studies provide insights into the reaction mechanism. In addition to this study using 4-Acetylpyridine, there are many other studies that have used 4-Acetylpyridine(cas: 1122-54-9Recommanded Product: 1122-54-9) was used in this study.

4-Acetylpyridine(cas: 1122-54-9) 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.Recommanded Product: 1122-54-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of Methyl 5-bromopicolinateIn 2011 ,《Fluorogenic N,O-chelates built on a C2-symmetric aryleneethynylene platform: Spectroscopic and structural consequences of conformational preorganization and ligand denticity》 appeared in Journal of Organometallic Chemistry. The author of the article were Park, Byung Gyu; Pink, Maren; Lee, Dongwhan. The article conveys some information:

Using π-extended aryleneethynylene as a rigid structural skeleton, a C2-sym. bis(picolinate) ligand I was prepared Binding of Zn(II) or Cd(II) ion to this formally tetradentate N2O2-chelate resulted in significant red shifts and enhancement in emission. The metal-ligand interaction responsible for such structural change was studied by isolation and characterization of a tetrazinc(II) complex, in which the picolinate group functions not only as terminal bidentate but also as bridging with its μ-1,3 carboxylate unit. In the experiment, the researchers used Methyl 5-bromopicolinate(cas: 29682-15-3Reference of Methyl 5-bromopicolinate)

Methyl 5-bromopicolinate(cas: 29682-15-3) 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 Methyl 5-bromopicolinate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Safety of 6-Bromopyridin-3-amineIn 2010 ,《Selective inducible microsomal prostaglandin E2 synthase-1 (mPGES-1) inhibitors derived from an oxicam template》 appeared in Bioorganic & Medicinal Chemistry Letters. The author of the article were Wang, Jane; Limburg, David; Carter, Jeff; Mbalaviele, Gabriel; Gierse, James; Vazquez, Michael. The article conveys some information:

Here we describe the SAR of a series of potent and selective mPGES-1 inhibitors based on an oxicam template. Compound 13j demonstrated low nanomolar mPGES-1 inhibition in an enzyme assay. In addition, it displayed PGE2 inhibition in a cell-based assay (0.42 μM) and had over 238-fold selectivity for mPGES-1 over COX-2 and over 200-fold selectivity for mPGES-1 over 6-keto PGF1α. In the part of experimental materials, we found many familiar compounds, such as 6-Bromopyridin-3-amine(cas: 13534-97-9Safety of 6-Bromopyridin-3-amine)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Safety of 6-Bromopyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Formula: C12H12N2In 2019 ,《Optimisation of octahedral iron(II) and cobalt(II) spin-crossover metal complex for thermoelectric application》 appeared in Materials Chemistry and Physics. The author of the article were Ibrahim, N. M. J. N.; Said, S. M.; Hasnan, M. M. I. M.; Sabri, M. F. M.; Abdullah, N.; Mainal, A.; Salleh, M. F. M.; Izam, T. F. T. M. N.. The article conveys some information:

Four spin-crossover (SCO) complexes with general formulas, [M2(CH3COO)4(L)2] and [M(L)3](BF4)2, where M = Fe(II) and Co(II), containing extended π-conjugated bipyridyl ligand and N3-Schiff bases appended with linear C16 carbon chains at the N atoms were successfully synthesized and characterized. Correlation of its structural properties to thermoelec. behavior was studied: (1)structure of complexes, (2)choice of metal center and (3)choice of counterions. The structure of the mol., i.e. mol. vs. ionic has the largest impact on the SCO behavior. The mol. complexes with higher percentage of high-spin (73.4% HS for Fe-dinuc and 78% HS for Co-dinuc) produced the highest Seebeck values in mV K-1 (-0.57 ± 0.01 for Fe-dinuc and -0.58 ± 0.01 for Co-dinuc) due to the weaker metal-to-ligand bonds resulting in the increase mobility of the I- during agglomeration formed, thus increased the entropy in the solution Addnl., choice of metal center also was a factor to determine the magnitude of Seebeck performance due to the spin state transition during electron transfer. For counterion effect, it has the effect of determining the sign of the Seebeck value where I- is easier to oxidize/reduce process compared to CH3COO- and BF4- due to lower redox potential. These findings will assist in a systematic mol. design pathway for high potential SCO complexes for thermoelec. applications. In addition to this study using 4,4′-Dimethyl-2,2′-bipyridine, there are many other studies that have used 4,4′-Dimethyl-2,2′-bipyridine(cas: 1134-35-6Formula: C12H12N2) was used in this study.

4,4′-Dimethyl-2,2′-bipyridine(cas: 1134-35-6) is used in the synthesis of a series of o-phenanthroline-substituted ruthenium(II) complexes.Formula: C12H12N2 Furthermore, 4,4′-Dimethyl-2,2′-bipyridine is used as a chemical Intermediate. It can be used for the determination of ferrous and cyanide compounds.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

SDS of cas: 13534-97-9In 2020 ,《Discovery of CPI-1612: A Potent, Selective, and Orally Bioavailable EP300/CBP Histone Acetyltransferase Inhibitor》 appeared in ACS Medicinal Chemistry Letters. The author of the article were Wilson, Jonathan E.; Patel, Gaurav; Patel, Chirag; Brucelle, Francois; Huhn, Annissa; Gardberg, Anna S.; Poy, Florence; Cantone, Nico; Bommi-Reddy, Archana; Sims, Robert J.; Cummings, Richard T.; Levell, Julian R.. The article conveys some information:

The histone acetyltransferases, CREB binding protein (CBP) and EP300, are master transcriptional co-regulators that have been implicated in numerous diseases, such as cancer, inflammatory disorders, and neurodegeneration. A novel, highly potent, orally bioavailable EP300/CBP histone acetyltransferase (HAT) inhibitor, CPI-1612 or 17, was developed from the lead compound 3. Replacement of the indole scaffold of 3 with the aminopyridine scaffold of 17 led to improvements in potency, solubility, and bioavailability. These characteristics resulted in a 20-fold lower efficacious dose for 17 relative to lead 3 in a JEKO-1 tumor mouse xenograft study. The experimental process involved the reaction of 6-Bromopyridin-3-amine(cas: 13534-97-9SDS of cas: 13534-97-9)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.SDS of cas: 13534-97-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Recommanded Product: 2-(2-Hydroxyethyl)pyridineIn 2018 ,《Coordination Chemistry of N-(2-Pyridylethyl)-Substituted Bulky Amidinates and Triazenides of Magnesium》 appeared in European Journal of Inorganic Chemistry. The author of the article were Kalden, Diana; Krieck, Sven; Goerls, Helmar; Westerhausen, Matthias. The article conveys some information:

The amidines Dipp-N:C(R)-NH(C2H4R’) [R = tBu, R’ = Ph (1a); R = Ph, R’ = Py (1b)] as well as 1-(2,4,6-triisopropylphenyl)-3-(2-pyridylethyl)triazene (1c) are magnesiated with com. available dibutylmagnesium yielding the complexes [(THF)Mg{Dipp-N:C(tBu)-N(C2H4Ph)}2] (3a), [Mg{Dipp-N:C(Ph)-N(C2H4Py)}2] (3b), and [Mg{Tripp-N:N-N(C2H4Py)}2] (3c). Handling and isolation of triazene 1c has been performed at room temperature or below to avoid elimination of dinitrogen and formation of 2-pyridylethyl-(2,4,6-triisopropylphenyl)amine (2). In the solid state, the compounds 1b and 1c form dimers via intermol. hydrogen bridges to the pyridyl groups of neighboring mols. The results came from multiple reactions, including the reaction of 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Recommanded Product: 2-(2-Hydroxyethyl)pyridine)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) 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. Recommanded Product: 2-(2-Hydroxyethyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 100-48-1In 2021 ,《Mechanochemical Release of Non-Covalently Bound Guests from a Polymer-Decorated Supramolecular Cage》 appeared in Angewandte Chemie, International Edition. The author of the article were Kueng, Robin; Pausch, Tobias; Rasch, Dustin; Goestl, Robert; Schmidt, Bernd M.. The article conveys some information:

Supramol. coordination cages show a wide range of useful properties including, but not limited to, complex mol. machine-like operations, confined space catalysis, and rich host-guest chemistries. Here we report the uptake and release of non-covalently encapsulated, pharmaceutically-active cargo from an octahedral Pd cage bearing polymer chains on each vertex. Six poly(ethylene glycol)-decorated bipyridine ligands are used to assemble an octahedral PdII6(TPT)4 cage. The supramol. container encapsulates progesterone and ibuprofen within its hydrophobic nanocavity and is activated by shear force produced by ultrasonication in aqueous solution entailing complete cargo release upon rupture, as shown by NMR and GPC analyses. In the experiment, the researchers used many compounds, for example, 4-Cyanopyridine(cas: 100-48-1Related Products of 100-48-1)

4-Cyanopyridine(cas: 100-48-1) 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. Related Products of 100-48-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem