Tag: 200-300

4-Aryl-1-oxa-4,9-diazaspiro[5.5]undecane derivatives as dual μ-opioid receptor agonists and σ₁ receptor antagonists for the treatment of pain was written by Garcia, Monica;Virgili, Marina;Alonso, Monica;Alegret, Carles;Fernandez, Begona;Port, Adriana;Pascual, Rosalia;Monroy, Xavier;Vidal-Torres, Alba;Serafini, Maria-Teresa;Vela, Jose Miguel;Almansa, Carmen. And the article was included in Journal of Medicinal Chemistry in 2020.HPLC of Formula: 72996-65-7 This article mentions the following:

The synthesis and pharmacol. activity of a new series of 1-oxa-4,9-diazaspiro[5.5]undecane derivatives as potent dual ligands for the sigma-1 receptor (σ₁R) and the μ-opioid receptor (MOR) are reported. The different positions of the central scaffold, designed using a merging strategy of both targets pharmacophores, were explored using a versatile synthetic approach. Phenethyl derivatives in position 9, substituted pyridyl moieties in position 4 and small alkyl groups in position 2 provided the best profiles. One of the best compounds, I, showed a balanced dual profile (i.e. MOR agonism and sigma antagonism) and potent analgesic activity, comparable to the MOR agonist oxycodone in the paw pressure test in mice. Contrary to oxycodone, as expected from the addition of σ₁R antagonism, I showed local, peripheral activity in this test, which was reversed by the σ₁R agonist PRE-084. At equianalgesic doses, I showed less constipation than oxycodone, providing evidence that dual MOR agonism and σ₁R antagonism may be a useful strategy for obtaining potent and safer analgesics. In the experiment, the researchers used many compounds, for example, 2-(2-Bromoethyl)pyridine hydrobromide (cas: 72996-65-7HPLC of Formula: 72996-65-7).

2-(2-Bromoethyl)pyridine hydrobromide (cas: 72996-65-7) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. 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. HPLC of Formula: 72996-65-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Palladium-Catalyzed Directed Halogenation of Bipyridine N-Oxides was written by Zucker, Sina P.;Wossidlo, Friedrich;Weber, Manuela;Lentz, Dieter;Tzschucke, C. Christoph. And the article was included in Journal of Organic Chemistry in 2017.Computed Properties of C8H8BrNO2 This article mentions the following:

The palladium-catalyzed directed C-H halogenation of bipyridine N-oxides was investigated. Using NCS or NBS (N-chloro- or N-bromosuccinimide) and 5 mol % Pd(OAc)₂ in chlorobenzene (0.10 M) at 110 °C, pyridine-directed functionalization took place and 3-chloro- or 3-bromobipyridine N-oxides were obtained in high yields. The reaction is sensitive to steric hindrance by 4- and 6′-substituents. Only in the latter case, where coordination of palladium by the pyridine is hindered, 3′-halogenation directed by the N-oxide function was observed The halogenated products were deoxygenated by PCl₃ or PBr₃. In the experiment, the researchers used many compounds, for example, Ethyl 2-bromoisonicotinate (cas: 89978-52-9Computed Properties of C8H8BrNO2).

Ethyl 2-bromoisonicotinate (cas: 89978-52-9) 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.Computed Properties of C8H8BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Thermal stability limits of imidazolium, piperidinium, pyridinium, and pyrrolidinium ionic liquids immobilized on metal oxides was written by Kurtoglu-Oztulum, Samira F.;Jalal, Ahsan;Uzun, Alper. And the article was included in Journal of Molecular Liquids in 2022.COA of Formula: C10H16BrN This article mentions the following:

Twenty-nine different ionic liquids (ILs) consisting of imidazolium, pyridinium, piperidinium, and pyrrolidinium cations and I^–, Cl^–, Br^–, PF^–₆, BF^–₄, [DCA]^–, and [NTf₂]^– anions were immobilized on MgO and SiO₂. Their short-term thermal stability limits were investigated by thermogravimetric anal. and compared with those of the corresponding bulk ILs. Data showed that the thermal stability limits of ILs change significantly when the ILs are immobilized on metal oxides. These changes were evaluated based on the structural interactions determined by IR spectroscopy. Systematic structural differences were considered to investigate the factors affecting the thermal stability of bulk ILs, and their counterparts immobilized on MgO and SiO₂. These structural changes were the change in the alkyl chain length, the methylation on C2 site in imidazolium ILs, the change in substituent position in the pyridinium ring, the change in the anion, and the change in the IL family. The strongest factor controlling the thermal stability limits of both bulk ILs and their supported counterparts was determined as the anion type. Accordingly, the basicity of the anion and the surface acidity of the metal oxide and their resulting interactions were found to have a significant effect on the thermal stability limits. Data presented here offer the opportunity to pick a suitable anion and cation pair according to the metal oxide, so that the supported IL can withstand the desired operation conditions in various applications, such as catalysis or gas separation In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6COA of Formula: C10H16BrN).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. 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.COA of Formula: C10H16BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Two-step synthesis of 3-aryl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones was written by Scott, Jeremy P.. And the article was included in Synlett in 2006.Safety of (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester This article mentions the following:

One-pot tandem palladium-catalyzed amination and intramol. amidation of tert-Bu (2-chloropyridin-3-yl)carbamate with substituted primary anilines allows for the preparation of 3-arylated 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones (49-90% yield) in two steps from com. available materials. In the experiment, the researchers used many compounds, for example, (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (cas: 209798-48-1Safety of (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester).

(2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (cas: 209798-48-1) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. 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.Safety of (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Structural Diversity of Cadmium(II) Coordination Polymers Induced by Tuning the Coordination Sites of Isomeric Ligands was written by Liu, Bo;Zhou, Hui-Fang;Hou, Lei;Wang, Jian-Ping;Wang, Yao-Yu;Zhu, Zhonghua. And the article was included in Inorganic Chemistry in 2016.Reference of 89978-52-9 This article mentions the following:

When the coordination sites of ligands were shifted, the solvothermal reactions of four positional isomeric asym. phenylpyridine-dicarboxylic acids with Cd(NO₃)₂ generated four new coordination polymers, [Cd(L1)(DMF)₃]·DMF·H₂O (1), [H₂NMe₂]₂[Cd(L2)₂]·3DMF·H₂O (2), [Cd(L3)(H₂O)₂] (3), and [Cd(L4)]·1.5DMF (4), where H₂L1 = 2-(3′-carboxylphenyl)isonicotinic acid, H₂L2 = 2-(4′-carboxylphenyl)isonicotinic acid, H₂L3 = 5-(3′-carboxylphenyl)nicotic acid, and H₂L4 = 2-(3′-pyridyl)terephthalic acid. 1 Shows a rare 2D fabric structure. 2 Discloses a grid-layer structure with heterochiral helical chains and in which three sets of layers stack in different directions, affording an unprecedented 2D + 2D + 2D → 3D polycatenating framework with 3D intersecting porous systems. 3 Also displays a 2D layer possessing strong intralayer π···π interactions and interlayer H bonds. 4 Contains a rare Cd₂(COO)₄ paddle-wheel unit and forms a 3D framework with 1D open channels. The carboxyl and pyridyl groups of the positional isomeric H₂L1-H₂L4 ligands show distinct bridging fashions, which gives versatile architectures of 1–4, and their effects on the crystal structures are discussed. 1–4 Reveal solid-state photoluminescence stemming from intraligand charge transfer. 2 And 4 show high selectivity for CO₂ over CH₄, but with different CO₂ adsorption enthalpies. Grand canonical Monte Carlo simulations identified the multiple adsorption sites in 2 for CO₂. In the experiment, the researchers used many compounds, for example, Ethyl 2-bromoisonicotinate (cas: 89978-52-9Reference of 89978-52-9).

Ethyl 2-bromoisonicotinate (cas: 89978-52-9) 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.Reference of 89978-52-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Derivatives of pyridine and quinoline. LXXXVIII. Reactions of bromo derivatives of 2- and 3-ethoxypyridines when heated with hydrochloric acid was written by den Hertog, H. J.;de Bruyn, J.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1951.Application of 13472-81-6 This article mentions the following:

Following abstract When a bromoethoxypyridine (0.01 mole in 30-40 ml. 25% aqueous HCl) in a sealed tube is heated 4 hrs. at 160° in a shaking furnace, the Br is replaced by Cl when the former is in the 2- or 6-position, and the EtO group is replaced by the OH group. Thus 6-bromo-2-ethoxypyridine (I) gives 6-chloro-2-hydroxypyridine (II), m. 128.5-9°, and 2-bromo-3-ethoxypyridine (III) gives 2-chloro-3-hydroxypyridine, m. 169-70°, plus the corresponding dihydroxypyridines. The 3,5-di-Cl derivative of I yields 3,5,6-trichloro-2-hydroxypyridine, m. 174-5°. When the Br is in the 3- or 5-position it is not substituted by the procedure given. Thus 5-bromo-3-ethoxypyridine yields 5-bromo-3-hydroxypyridine. But either 3- or 5-bromo-2-ethoxypyridine yields mixtures of 3,5-dibromo-2-hydroxypyridine and 2-hydroxypyridine. As a further example of the positional reactivity of the Br, 2,5,6-tri-bromo-3-ethoxypyridine, m. 86-7°, prepared by heating 3-bromo-5-ethoxypyridine with Br in a sealed tube at 100°, gave 5-bromo-2,6-dichloro-3-ethoxypyridine, m. 77-8° with aqueous HCl. The EtO group in this case remained intact. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6Application of 13472-81-6).

3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application of 13472-81-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Oxidation of styrylpyridinium dyes by permanganate ion was written by Dash, Sukalyan;Mishra, Bijay K.. And the article was included in Bulletin of the Chemical Society of Japan in 1994.Synthetic Route of C10H16BrN This article mentions the following:

The oxidation of N-alkyl substituted styrylpyridinium bromides in both KMnO₄ and cetyltrimethylammonium permanganate (CTAP) results in the formation of both of the corresponding substituted benzaldehydes. The oxidation in aqueous medium is catalyzed by acid whereas in CHCl₃ the reaction proceeds under neutral conditions. However, the reaction proceeds through the same mechanism in both the media. The faster rate of oxidation in aqueous medium by KMnO₄ than that in CHCl₃ medium by CTAP is rationalized through a hydrophobic effect. The overall rate equation can be represented as rate = k[Substrate]^1.5[Oxidant]^-0.75 in aqueous medium and rate = k[Substrate]^0.5[Oxidant]^-1 in CHCl₃. From the substituent effect a transition state with low electron d. at the olefinic carbon is proposed. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Synthetic Route of C10H16BrN).

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. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Synthetic Route of C10H16BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Full-color-tunable phosphorescence of antimony-doped lead halide single crystal was written by Liao, Jin-Feng;Zhang, Zhipeng;Wang, Bingzhe;Tang, Zikang;Xing, Guichuan. And the article was included in npj Flexible Electronics in 2022.COA of Formula: C10H16BrN This article mentions the following:

Although multiple emissive phosphors are of great fundamental interest and practical importance, it is still challenging to achieve full-color tunable luminescence in a single-component material. Herein, we present an antimony-doped lead halide single crystal (C₁₀NH₂₂)₂PbBr₄: Sb³⁺ with widely tunable red/green/blue/white luminescence. Extrinsic Sb³⁺ dopants provide host another active sites to capture photo-generated excitons, thus triggering blue/red dual emission. Moreover, a reversible thermal-induced phase transition transforms blue/red emission into green/red dual emission. Both two phases exhibit intriguing excitation-wavelength dependent emission, affording a whole color gamut covering the red-green-blue (RGB) color triangle on the CIE 1931 diagram. Exptl. and theor. calculation studies reveal two emitters work independently, which paves the way for the multimode optical control and promotes the development of multifunctional luminescent materials. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6COA of Formula: C10H16BrN).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). 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.COA of Formula: C10H16BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Configurationally Stable Biaryl Analogues of 4-(Dimethylamino)pyridine: A Novel Class of Chiral Nucleophilic Catalysts was written by Spivey, Alan C.;Fekner, Tomasz;Spey, Sharon E.;Adams, Harry. And the article was included in Journal of Organic Chemistry in 1999.Synthetic Route of C10H13BrN2O2 This article mentions the following:

A short synthetic approach toward a novel class of chiral nucleophilic catalysts, the dissymmetry of which stems from restricted rotation about an aryl-aryl bond, was developed. The key steps of the synthesis include preparation of a nucleophilic 1-methyl-2-pyrrolino[3,2-c]pyridine core by ortho-lithiation and creation of the biaryl axes via Suzuki cross-coupling reactions. Comparative HPLC studies of racemization for configurationally labile biaryls containing 1-methyl-2-pyrrolino[3,2-c]pyridine, 4-(dimethylamino)pyridine, and 4-(1-pyrrolidino)pyridine cores, resp., demonstrated that a pyrrolidino substituent ortho to the biaryl axis is optimal for slowing aryl-aryl rotation. Biaryls containing all 3 cores were shown to retain DMAP-like catalytic activity in the acylation of a hindered alc. 1-Methyl-7-(2-methyl- and -phenyl-1-naphthyl)-2-pyrrolino[3,2-c]pyridine, which are configurationally stable at ambient temperature, also were prepared via modification of configurationally labile derivatives These compounds in optically pure form should provide a useful starting point for studies on catalytic asym. acyl transfer using atropisomeric analogs of DMAP. In the experiment, the researchers used many compounds, for example, tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9Synthetic Route of C10H13BrN2O2).

tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). 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. Synthetic Route of C10H13BrN2O2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

{[Cd(bpo)(SCN)₂]·CH₃CN}_n: A Novel Three-Dimensional (3D) Noninterpenetrated Channel-Like Open Framework with Porous Properties was written by Du, Miao;Chen, Shen-Tan;Bu, Xian-He. And the article was included in Crystal Growth & Design in 2002.Reference of 15420-02-7 This article mentions the following:

Reaction of CdCl₂·0.5H₂O with 2,5-bis(4-pyridyl)-1,3,4-oxodiazole (bpo) and NH₄SCN in a 1:1:2 molar ratio under MeCN-H₂O medium afforded a novel neutral three-dimensional (3D) coordination polymer {[Cd(bpo)(SCN)₂]·MeCN}_n (1) [monoclinic, space group P2₁/c, a 7.680(2), b 10.029(3), c 25.786(7) Å, β 93.779(5)°, Z = 4]. The crystal structure reveals that 1 has a 3-dimensional noninterpenetrating open framework with guest MeCN mols. in the cavities, in which the Cd^II centers (with CdN₄S₂ octahedral geometry) are bridged by the bpo mols. and SCN^– groups. It is interesting that the two-dimensional sheet in this 3-dimensional network consists of 16-membered [Cd₄(μ-SCN-N,S)₄] rings, and the bpo mols. extend these layers to a 3-dimensional structure, which is further stabilized by C-H…N H-bonding and strong π-π-stacking interactions. TGA and x-ray powder diffraction technique measurements illustrate that the framework of 1 is retained upon removal of the uncoordinated guest MeCN mols., indicating that 1 might be used to generate microporous material. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Reference of 15420-02-7).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) 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. 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.Reference of 15420-02-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem