Tag: 200-300

Discovery of Potent and Selective Transient Receptor Potential Vanilloid 1 (TRPV1) Agonists with Analgesic Effects In Vivo Based on the Functional Conversion Induced by Altering the Orientation of the Indazole Core was written by Liang, Qianqian;Qiao, Zhen;Zhou, Qiqi;Xue, Dengqi;Wang, KeWei;Shao, Liming. And the article was included in Journal of Medicinal Chemistry in 2022.Related Products of 175205-82-0 This article mentions the following:

Reported the synthesis of N-indazole-4-aryl piperazine carboxamide I[R¹ = H, Me; R = 3-MeC₆H₅, 5-ClC₆H₅, 3-BrC₆H₅ etc.] analogs as TRPV1 modulators. The structure-activity relationship (SAR) revealed that substituting indazole at the 5-/6-position leads to TRPV1 agonism, whereas the 4- and 7-positions of indazole obtain mild antagonism and loss of activity, resp. The whole-cell clamp patch assay shows that I[R = H; R1 = 2,3-diClC₆H₅] a potent and selective TRPV1 agonist and it relieves inflammatory and thermal pain by desensitizing the native TRPV1 current in the dorsal root ganglion (DRG) in mice. Addnl., site-directed mutagenesis combined with mol. docking shows an important hydrogen interaction between Arg557 and the indazole of comp. I[R = H; R1 = 2,3-diClC₆H₅]. Taken together, our findings provided insight into TRPV1 agonism-antagonism conversion based on the interaction between indazole and Arg557, which provided a strategy to obtain new TRPV1 agonists by structural modification of antagonists. Compound I[R = H; R1 = 2,3-diClC₆H₅] used as a lead compound for further optimization. In the experiment, the researchers used many compounds, for example, 2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0Related Products of 175205-82-0).

2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0) 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. 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. Related Products of 175205-82-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki-Miyaura Coupling of 3,5- and 4,6-Dibromo-2-tosyloxypyridines was written by Park, Cho-Hee;Kwon, Yong-Ju;Oh, In-Young;Kim, Won-Suk. And the article was included in Advanced Synthesis & Catalysis in 2017.Safety of 3,5-Dibromo-2-hydroxypyridine This article mentions the following:

Chemoselective Suzuki-Miyaura reactions on 3,5- and 4,6-dibromo-2-tosyloxypyridines was studied for the preparation of trisubstituted pyridines I [Ar = Ph, 3-thienyl, 2-benzothiophenyl, etc.] and II. Further functionalization such as palladium-catalyzed amination and copper-free Sonogashira reaction of the tosylate group in the diarylpyridine derivatives obtained was accomplished for the synthesis of novel and biol. relevant trisubstituted pyridines. The formal synthesis of ficuseptine, a bioactive alkaloid, was also achieved via palladium-catalyzed cross-coupling reaction of 3,5-dibromo-2-tosyloxypyridine from 3,5-dibromo-2-hydroxypyridine with 50% overall yield. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6Safety of 3,5-Dibromo-2-hydroxypyridine).

3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6) 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. 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 3,5-Dibromo-2-hydroxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Expansion of Azulenes as Nonbenzenoid Aromatic Compounds for C-H Activation: Rhodium- and Iridium-Catalyzed Oxidative Cyclization of Azulene Carboxylic Acids with Alkynes for the Synthesis of Azulenolactones and Benzoazulenes was written by Maeng, Chanyoung;Son, Jeong-Yu;Lee, Seung Cheol;Baek, Yonghyeon;Um, Kyusik;Han, Sang Hoon;Ko, Gi Hoon;Han, Gi Uk;Lee, Kyungsup;Lee, Kooyeon;Lee, Phil Ho. And the article was included in Journal of Organic Chemistry in 2020.Reference of 65350-59-6 This article mentions the following:

Rhodium-catalyzed oxidative [4+2] cyclization reactions through the C-H activation of azulene carboxylic acids as nonbenzenoid aromatic compounds with sym. and unsym. alkynes were developed under aerobic conditions, which produced azulenolactone derivatives with a wide substrate scope and excellent functional group tolerance. Interestingly, azulenic acids in reaction with alkynes underwent iridium-catalyzed [2+2+2] cyclization accompanied by decarboxylation to afford tetra(aryl)-substituted benzoazulene derivatives The reactivity order for C-H activation reaction was greater toward azulene-6-carboxylic acid, azulene-1-carboxylic acid and azulene-2-carboxylic acid. For the first time, the expansion of azulenes having directing group as nonbenzenoid aromatic compounds for C-H activation was successful, indicating that nonbenzenoid aromatic compounds can be used as good substrates for the C-H activation reaction. Therefore, the research area of C-H activation will certainly expand to nonbenzenoid aromatic compounds in future. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Reference of 65350-59-6).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Reference of 65350-59-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis and characterization of copper(I) and silver(I) complexes with heterocyclic bidentate ligands (N, X), X = S, Se was written by Sousa-Pedrares, Antonio;Duran-Carril, Maria Luz;Romero, Jaime;Arturo Garcia-Vazquez, J.;Sousa, Antonio. And the article was included in Inorganica Chimica Acta in 2010.Application In Synthesis of 2-Bromo-3-(trifluoromethyl)pyridine This article mentions the following:

The synthesis and structural characterization of series of copper and silver homoleptic complexes [M(R-pyX)] (py = 2-pyridine, M = Cu, Ag, X = S, Se; R = H, 3-CF₃, 5-CF₃ (not all combinations)), is described. The copper compounds, as well as [Ag(pySe)] and [Ag(3-CF₃-pySe)], were synthesized by electrochem. oxidation of anodic metal in a cell containing an acetonitrile solution of the corresponding proligand. The other homoleptic silver complexes were obtained by direct reaction between AgNO₃ and the salt of the corresponding ligand in methanol. The reaction of the metal thiolate compounds with bis(diphenylphosphino)ethane (dppe) in acetone gave heteroleptic compounds [M₂(R-pyX)₂(dppe)₃]. The compounds obtained were characterized by microanal., IR spectroscopy and mass spectrometry and, in cases where the complexes were sufficiently soluble, by ¹H NMR spectroscopy. The proligands (3-CF₃pySe)₂ (1), (5-CF₃-pySe)₂ (2) and (5-CF₃-pySe-DMF) (3) and [Cu(3-CF₃-pyS)] (4), [Ag(3-CF₃-pyS)] (5) and [Cu₂(5-CF₃-pyS)₂(dppe)₃] (6) were obtained as crystalline products and were studied by x-ray diffraction methods. In the experiment, the researchers used many compounds, for example, 2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0Application In Synthesis of 2-Bromo-3-(trifluoromethyl)pyridine).

2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Application In Synthesis of 2-Bromo-3-(trifluoromethyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Conductivity enhancement of PEDOT/PSS films with ionic liquids as dopants was written by Lee, Sungkoo;Lee, Kyeong K.. And the article was included in Advanced Materials Research (Zuerich, Switzerland) in 2010.Name: 1-Butyl-4-methylpyridin-1-ium bromide This article mentions the following:

The ionic materials were added to PEDOT/PSS solution as secondary dopants. The conductivity of PEDOT/PSS film improved with adding ionic materials. The film of PEDOT/PSS with 1% pyridinium p-toluene-sulfonate showed the conductivity of 23S/cm, which is increased about three orders than the film of origin PEDOT/PSS with 0.028S/cm. The surface morphol. of films of PEDOT/PSS mixture is investigated by at. force microscope. The AFM showed the increasing of grain size with the addition of pyridinium p-toluene-sulfonate. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Name: 1-Butyl-4-methylpyridin-1-ium bromide).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) 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. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Name: 1-Butyl-4-methylpyridin-1-ium bromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A One-Pot Sonogashira Coupling and Annulation Reaction: An Efficient Route toward 4H-Quinolizin-4-ones was written by Chen, Zhengwang;Liu, Tanggao;Ma, Xiaoyue;Liang, Pei;Long, Lipeng;Ye, Min. And the article was included in Synlett in 2019.Recommanded Product: Methyl 2-(5-bromopyridin-2-yl)acetate This article mentions the following:

An efficient one-pot Sonogashira coupling and annulation reaction affording 4H-quinolizin-4-ones I (R¹ = Ph, 3-MeC₆H₄, 2-thienyl, etc.; R² = MeO₂C, EtO₂C, CN, etc.; R³ = H, Br, Me) from iodoarenes R¹I, 2-R²CH₂-5-R³-substituted pyridines and Me propiolate in moderate to excellent yields is described. A variety of substituted iodoarenes and 2-alkylpyridines were well tolerated, and especially the unsaturated double and triple bonds were compatible under the standard conditions. In the experiment, the researchers used many compounds, for example, Methyl 2-(5-bromopyridin-2-yl)acetate (cas: 917023-06-4Recommanded Product: Methyl 2-(5-bromopyridin-2-yl)acetate).

Methyl 2-(5-bromopyridin-2-yl)acetate (cas: 917023-06-4) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Recommanded Product: Methyl 2-(5-bromopyridin-2-yl)acetate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis and biological evaluation of 4-carbamoyl-2-β-D-ribofuranosylpyridine was written by Joos, Pieter E.;Esmans, Eddy L.;Dommisse, Roger A.;Van Dongen, Walter;Lepoivre, Jozef A.;Alderweireldt, Frank C.;Balzarini, Jan;De Clercq, Erik. And the article was included in Nucleosides & Nucleotides in 1991.Application In Synthesis of Ethyl 2-bromoisonicotinate This article mentions the following:

The biol. evaluation and preparation of the title compound (I) and it α-anomer from 2-amino-4-methylpyridine, via addition reaction of lithio(dimethyloxazolinyl)pyridine II with 2,4:3,5-di-O-benzylidenealdehydo-D-ribose (III), are reported. I showed no appreciable virucidal activity and was a weak cytostatic agent in a number of tumor cell systems. In the experiment, the researchers used many compounds, for example, Ethyl 2-bromoisonicotinate (cas: 89978-52-9Application In Synthesis of Ethyl 2-bromoisonicotinate).

Ethyl 2-bromoisonicotinate (cas: 89978-52-9) 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.Application In Synthesis of Ethyl 2-bromoisonicotinate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Study of Heterogeneous Catalysis by Iron-Squarate based 3D Metal Organic Framework for the Transformation of Tetrazines to Oxadiazole derivatives was written by Goswami, Soumyabrata;Jena, Himanshu Sekhar;Konar, Sanjit. And the article was included in Inorganic Chemistry in 2014.Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole This article mentions the following:

We present here a simple, milder, and environmentally benign heterogeneous catalytic method for the transformation of tetrazines to oxadiazole derivatives at room temperature (25 °C) using our earlier synthesized iron-squarate based 3D metal organic framework, [Fe₃(OH)₃(C₄O₄)(C₄O₄)_0.5]_n (FeSq-MOF). In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. 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.Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Gold-Catalyzed Direct Alkynylation of Azulenes was written by Szekely, Anna;Peter, Aron;Aradi, Klara;Tolnai, Gergely L.;Novak, Zoltan. And the article was included in Organic Letters in 2017.Formula: C10H16BrN This article mentions the following:

A novel catalytic method for the direct C-H alkynylation of azulenes is developed. The gold catalyzed functionalization of this special carbacycle is achieved with hypervalent iodonium reagent TIPS-EBX under mild reaction conditions. With the aid of the developed procedure, several TIPS alkynylated azulene derivatives, e.g., I, were synthesized bearing important functional groups for further functionalization. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Formula: C10H16BrN).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Formula: C10H16BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Theoretical Probing of Weak Anion-Cation Interactions in Certain Pyridinium-Based Ionic Liquid Ion Pairs and the Application of Molecular Electrostatic Potential in Their Ionic Crystal Density Determination: A Comparative Study Using Density Functional Approach was written by Joseph, Aswathy;Thomas, Vibin Ipe;Zyla, Gawel;Padmanabhan, A. S.;Mathew, Suresh. And the article was included in Journal of Physical Chemistry A in 2018.Safety of 1-Butyl-4-methylpyridin-1-ium bromide This article mentions the following:

A comprehensive study on the structure, nature of interaction, and properties of six ionic pairs of 1-butylpyridinium and 1-butyl-4-methylpyridinium cations in combination with tetrafluoroborate (BF₄^–), chloride (Cl^–), and bromide (Br^–) anions have been carried out using d. functional theory (DFT). The anion-cation interaction energy (ΔE_int), thermochem. values, theor. band gap, MO energy order, DFT-based chem. activity descriptors [chem. potential (μ), chem. hardness (η), and electrophilicity index (ω)], and distribution of d. of states (DOS) of these ion pairs were investigated. The ascendancy of the -CH₃ substituent at the fourth position of the 1-butylpyridinium cation ring on the values of ΔE_int, theor. band gap and chem. activity descriptors was evaluated. The ΔE_int values were neg. for all six ion pairs and were highest for Cl^– containing ion pairs. The theor. band gap value after -CH₃ substitution increased from 3.78 to 3.96 eV (for Cl^–) and from 2.74 to 2.88 eV (for Br^–) and decreased from 4.9 to 4.89 eV (for BF₄^–). Ion pairs of BF₄^– were more susceptible to charge transfer processes as inferred from their significantly high η values and comparatively small difference in ω value after -CH₃ substitution. The change in η and μ values due to the -CH₃ substituent is negligibly small in all cases except for the ion pairs of Cl^–. Critical-point (CP) analyses were carried out to investigate the AIM topol. parameters at the interionic bond critical points (BCPs). The RDG isosurface anal. indicated that the anion-cation interaction was dominated by strong H_cat···X_ani and C_cat···X_ani interactions in ion pairs of Cl^– and Br^– whereas a weak van der Waal’s effect dominated in ion pairs of BF₄^–. The mol. electrostatic potential (MESP)-based parameter ΔΔV_min measuring the anion-cation interaction strength showed a good linear correlation with ΔE_int for all 1-butylpyridinium ion pairs (R² = 0.9918). The ionic crystal d. values calculated by using DFT-based MESP showed only slight variations from exptl. reported values. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Safety of 1-Butyl-4-methylpyridin-1-ium bromide).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. 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.Safety of 1-Butyl-4-methylpyridin-1-ium bromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem