Tag: 100-200

A New Series of Orally Bioavailable Chemokine Receptor 9 (CCR9) Antagonists; Possible Agents for the Treatment of Inflammatory Bowel Disease was written by Kalindjian, S. Barret;Kadnur, Sanjay V.;Hewson, Christopher A.;Venkateshappa, Chandregowda;Juluri, Suresh;Kristam, Rajendra;Kulkarni, Bheemashankar;Mohammed, Zainuddin;Saxena, Rohit;Viswanadhan, Vellarkad N.;Aiyar, Jayashree;McVey, Donna. And the article was included in Journal of Medicinal Chemistry in 2016.Reference of 76005-99-7 This article mentions the following:

Chemokine receptor 9 (CCR9), a cell surface chemokine receptor which belongs to the G protein-coupled receptor, 7-trans-membrane superfamily, is expressed on lymphocytes in the circulation and is the key chemokine receptor that enables these cells to target the intestine. It has been proposed that CCR9 antagonism represents a means to prevent the aberrant immune response of inflammatory bowel disease in a localized and disease specific manner and one which is accessible to small mol. approaches. One possible reason why clin. studies with vercirnon, a prototype CCR9 antagonist, were not successful may be due to a relatively poor pharmacokinetic (PK) profile for the mol. We wish to describe work aimed at producing new, orally active CCR9 antagonists based on the 1,3-dioxoisoindoline skeleton. This study led to a number of compounds that were potent in the nanomolar range and which, on optimization, resulted in several possible preclin. development candidates with excellent PK properties. In the experiment, the researchers used many compounds, for example, 2-Methoxy-4-methylpyridin-3-amine (cas: 76005-99-7Reference of 76005-99-7).

2-Methoxy-4-methylpyridin-3-amine (cas: 76005-99-7) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol� in pyridine vs. 150 kJ·mol� in benzene). Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Reference of 76005-99-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Fast Olefin Metathesis at Low Catalyst Loading was written by Peeck, Lars H.;Savka, Roman D.;Plenio, Herbert. And the article was included in Chemistry – A European Journal in 2012.Synthetic Route of C10H17NO2 This article mentions the following:

Reactions of the Grubbs 3rd generation complexes [RuCl₂(NHC)(Ind)(Py)] (N-heterocyclic carbene (NHC)=1,3-bis(2,4,6-trimethylphenylimidazolin)-2-ylidene (SIMes), 1,3-bis(2,6-diisopropylphenylimidazolin)-2-ylidene (SIPr), or 1,3-bis(2,6-diisopropylphenylimidazol)-2-ylidene (IPr); Ind = 3-phenylindenylid-1-ene, Py = pyridine) with 2-ethenyl-N-alkylaniline (alkyl = Me, Et) gave the new N-Grubbs-Hoveyda-type complexes 5 (NHC = SIMes, alkyl = Me), 6 (SIMes, Et), 7 (IPr, Me), 8 (SIPr, Me), and 9 (SIPr, Et) with N-chelating benzylidene ligands in yields of 50-75%. Compared to their, resp., conventional, O-Grubbs-Hoveyda complexes, the new complexes were characterized by fast catalyst activation, which translates into fast and efficient ring-closing metathesis (RCM) reactivity. Catalyst loadings of 15-150 ppm (0.0015-0.015 mol %) are sufficient for the conversion of a wide range of diolefinic substrates into the resp. RCM products after 15 min at 50° in toluene; compounds 8 and 9 are the most catalytically active complexes. The use of complex 8 in RCM reactions enables the formation of N-protected 2,5-dihydropyrroles with turnover numbers (TONs) of up to 58,000 and turnover frequencies (TOFs) of up to 232,000 h^-1; the use of the N-protected 1,2,3,6-tetrahydropyridines proceeds with TONs of up to 37,000 and TOFs of up to 147,000 h^-1; and the use of the N-protected 2,3,6,7-tetrahydroazepines proceeds with TONs of up to 19,000 and TOFs of up to 76,000 h^-1, with yields for these reactions ranging from 83-92%. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Synthetic Route of C10H17NO2).

tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) 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.Synthetic Route of C10H17NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ruthenium-catalyzed C-H allylation of arenes with allylic amines was written by Yan, Rui;Wang, Zhong-Xia. And the article was included in Organic & Biomolecular Chemistry in 2018.Synthetic Route of C12H11N This article mentions the following:

The Ru-catalyzed pyridyl-directed C-H allylation of arenes with allylic amines was developed. This reaction was carried out in the presence of 5 mol% of [Ru(p-cymene)Cl₂]₂ and 0.5 equivalent of AgOAc in CF₃CH₂OH at 75°, afforded the allylated products of arenes in moderate to excellent yields. The method exhibited a wide scope of allylic amines and arenes and showed a good compatibility of functional groups. The pyrazolyl- and pyrimidyl-directed C-H allylation of arenes were also performed under the same conditions. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Synthetic Route of C12H11N).

2-(m-Tolyl)pyridine (cas: 4373-61-9) 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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Synthetic Route of C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Relative retentions of C1-15 alkyl- and alkenylpyridines over different columns and at various temperatures was written by Oszczapowicz, Janusz;Golab, John;Pines, Herman. And the article was included in Journal of Chromatography in 1972.Application of 27876-24-0 This article mentions the following:

The relative retentions of fifty 2- and 4-alkyl- and alkenylpyridines were determined over 4 different gas-liquid chromatog. columns and at various temperatures The relation between the structure of the pyridines and their relative retention times is discussed. In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0Application of 27876-24-0).

4-Hexylpyridine (cas: 27876-24-0) 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Application of 27876-24-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Size-tunable ZnO nanotapes as an efficient catalyst for oxidative chemoselective C-B bond cleavage of arylboronic acids was written by Phukan, Shreemoyee;Mahanta, Abhijit;Rashid, Harunar Md.. And the article was included in Applied Catalysis, A: General in 2018.Synthetic Route of C6H7NO2 This article mentions the following:

Herein, we report a simple but effective chem. approach for the synthesis of size-tunable ZnO nanotapes by precipitation method in the presence of phytochems. present in the flower extract of Lantana camara plant. The electron microscopic study confirmed that the size of ZnO nanotapes can be systematically controlled by varying the concentration of either flower extract or metal ions and the flower extract played the key role in controlling the growth of ZnO nanotapes. The phase and crystalline anal. was carried out by X-ray diffraction method which indicated that ZnO nanostructures are highly crystalline in nature and are free from any impurities. The synthesized ZnO nanostructures exhibited interesting optical properties as investigated by UV-vis absorption and photoluminescence spectroscopy. Further the surface functionalities affect the optical properties of ZnO nanostructures which possess relatively strong UV emissions; a blue emission and a green emission. The synthesized ZnO nanostructures showed excellent catalytic properties in the ipso-hydroxylation of different aryl/ hetero-arylboronic acid to phenol in a relatively greener reaction conditions. These catalysts are highly stable and are re-usable upto six cycles of ipso-hydroxylation without losing its catalytic properties. In the experiment, the researchers used many compounds, for example, 5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0Synthetic Route of C6H7NO2).

5-Hydroxy-2-methoxylpyridine (cas: 51834-97-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. 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 C6H7NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A novel 1,2-alkyl migration of [trialkyl(4-pyridyl)borates] was written by Ishikura, Minoru;Ohta, Tsukasa;Terashima, Masanao. And the article was included in Heterocycles in 1986.Quality Control of 4-Hexylpyridine This article mentions the following:

4-Alkylpyridines were prepared from trialkyl(4-pyridyl)borates via the 1,2-alkyl migration in the presence of Lewis acids or acylating agents. Trialkyl(4-pyridyl)borates also reacted with 3-indolylacetyl chloride to yield an unstable dieneamide and 4-alkylpyridine. In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0Quality Control of 4-Hexylpyridine).

4-Hexylpyridine (cas: 27876-24-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Quality Control of 4-Hexylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Cyano adducts of 1-substituted pyridinium salts was written by Reuss, Robert H.;Smith, Nelson G.;Winters, Lawrence J.. And the article was included in Journal of Organic Chemistry in 1974.Name: 1-(Cyanomethyl)pyridin-1-ium chloride This article mentions the following:

The preparation and characterization of 10 cyano adducts I (R = 4-pyridyl, CH2OMe, Ph, etc.) from 1-substituted pyridinium salts II (X = Cl, Br) is described. In addition, the first Reissert-like compound (III) from pyridine is reported. I are relatively stable. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3Name: 1-(Cyanomethyl)pyridin-1-ium chloride).

1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) 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. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Name: 1-(Cyanomethyl)pyridin-1-ium chloride

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pyridine N-oxides as catalysts for thione-thiol rearrangement was written by Harano, Kazunobu;Shinohara, Ikuo;Murase, Motoji;Hisano, Takuzo. And the article was included in Heterocycles in 1987.Quality Control of 3,5-Dimethylpyridine 1-oxide This article mentions the following:

Rearrangement of O-alkyl S-Me dithiocarbonates I (R = Me, Et, Pr, CHMe₂, cyclohexyl, PhCH₂) in the presence of pyridine N-oxide (II; R¹ = R² = H) gave S-alkyl S-Me dithiocarbonates III in 62-98% yields. A solid-phase copolymer of 4-vinylpyridine N-oxide was also a useful catalyst. Rearrangement of I (R = Et) with II (R¹ = Ph, R² = H; R¹ = H, R² = Br) gave 20 and 31% III (R = Et), resp. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Quality Control of 3,5-Dimethylpyridine 1-oxide).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) 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. 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.Quality Control of 3,5-Dimethylpyridine 1-oxide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Design and Identification of a Novel, Functionally Subtype Selective GABA_A Positive Allosteric Modulator (PF-06372865) was written by Owen, Robert M.;Blakemore, David;Cao, Lishuang;Flanagan, Neil;Fish, Rebecca;Gibson, Karl R.;Gurrell, Rachel;Huh, Chan Woo;Kammonen, Juha;Mortimer-Cassen, Elisabeth;Nickolls, Sarah A.;Omoto, Kiyoyuki;Owen, Dafydd;Pike, Andy;Pryde, David C.;Reynolds, David S.;Roeloffs, Rosemarie;Rose, Colin;Stead, Clara;Takeuchi, Mifune;Warmus, Joseph S.;Watson, Christine. And the article was included in Journal of Medicinal Chemistry in 2019.Recommanded Product: 3939-12-6 This article mentions the following:

The design, optimization, and evaluation of a series of novel imidazopyridazine-based subtype-selective pos. allosteric modulators (PAMs) for the GABA_A ligand-gated ion channel are described. From a set of initial hits multiple subseries were designed and evaluated based on binding affinity and functional activity. As designing in the desired level of functional selectivity proved difficult, a probability-based assessment was performed to focus the project’s efforts on a single subseries that had the greatest odds of delivering the target profile. These efforts ultimately led to the identification of two precandidates from this subseries, which were advanced to preclin. safety studies and subsequently to the identification of the clin. candidate PF-06372865. In the experiment, the researchers used many compounds, for example, 6-Fluoronicotinonitrile (cas: 3939-12-6Recommanded Product: 3939-12-6).

6-Fluoronicotinonitrile (cas: 3939-12-6) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of âˆ?8.7 × 10âˆ? cm3·molâˆ?.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·molâˆ? in the liquid phase and 140.4 kJ·molâˆ? 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: 3939-12-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Physical properties and chemical constitution. Part XXVIII. Pyridine derivatives was written by Kyte, Colin T.;Jeffery, George H.;Vogel, Arthur I.. And the article was included in Journal of the Chemical Society in 1960.SDS of cas: 27876-24-0 This article mentions the following:

Purified samples of the following were prepared: pyridine, 2-, 3-, and 4-alkyl (Me to n-heptyl), Ac, and CHO derivatives of pyridine, 2-, and 3-(hydroxymethyl)pyridine, alkyl (Me to heptyl) esters of picolinic, nicotinic, and isonicotinic acids, 2,3-, 2,6-, 2,5-, and 3,5-lutidine, dialkyl oxalates, and aliphatic aldehydes. Refractive indexes at 20° (C, D, F, G’ lines), densities, and surface tensions at 20°, 40°, 60°, and 85°, parachors, mol. refractivities, and mol. refraction coefficients for these compounds were determined and tabulated. The mean values for CH₂ in parachors, mol. refractivities, and mol. refraction coefficients for mono- and dialkylpyridines, alkyl nicotinates, picolinates, and isonicotinates, as well as the corresponding constants for the 2-, 3-, and 4-pyridyl group, were measured. Ultraviolet and infrared spectra of the pyridine derivatives were taken. Pyridine was purified by the complex (C₅H₅N)₂.ZnCl₂.HCl followed by regeneration and fractionation. Thus, 80 ml. pyridine was added with stirring to 68 g. ZnCl₂ and 42 ml. concentrated HCl in 200 ml. absolute EtOH, the mixture cooled, the precipitate washed with EtOH, and air-dried, m. 153° (absolute EtOH). Also α-picoline was purified through (2-MeC₅H₄)₂.ZnCl₂.HCl, m. 118.5-19.5° (absolute EtOH). γ-Picoline was purified by preparing (4-MeC₅H₄N)₂.ZnCl₂.HCl, m. 130-0.5° (absolute EtOH), regenerating the base, treating with urea to remove 2,6-lutidine, and fractionally freezing in a special apparatus (description given). Impurities were removed from β-picoline by treatment with Ac₂O-phthalic anhydride according to a modified procedure of Riethof, et al. (CA 40, 5433⁷). The lutidines were usually purified by fractional distillation, conversion to a solid derivative, regeneration of the base, and fractional freezing. Preparation of the urea complexes of 2,3- and 2,6-lutidine, of 2,4-lutidine-HCl, and PhOH-2,5-lutidine complex, m. 57.5° (petr. ether), was described. Fractional distillation and freezing gave pure 3,5-lutidine. The 2-, 3-, and 4-alkylpyridines were prepared by alkylation of the corresponding picolines with alkyl chlorides in the presence of NaNH₂ (Chichibabin, CA 30, 8208⁹, 32, 4984⁸). Only monoalkylation occurred with α-picoline and colloidal NaNH₂ in xylene at 140°, but with γ-picoline at 0°, about 36% mono- and 20 % dialkylated product formed. Formation of dialkylated γ-picoline was avoided by alkylation in liquid NH₃. Satisfactory monoalkylation of β-picoline required liquid NH₃ solutions of NaNH₂ prepared in situ. sec-Alkylpyridines were readily prepared in liquid NH₃ by using 2 equivalents NaNH₃ and an alkyl chloride. The preferred method of preparing pure monoethylpyridines was the Wolff-Kishner reduction of the Ac compounds 4-Alkylpyridines (Et to Bu) were prepared from pyridine by a modified Wibaut-Arens synthesis (CA 35, 5894⁵; 37, 5063⁵). Similarly, 4-ethyl-3-methylpyridine was prepared from β-picoline. KMnO₄ oxidation of purified picolines gave pure pyridine monocarboxylic acids whose lower alkyl esters were prepared with HCl catalyst, the higher ones with H₂SO₄ catalyst, or by treating the acid chloride hydrochloride with the alc. EtOAc was condensed with Et pyridinecarboxylates by NaOEt or NaH in dry xylene followed by acid hydrolysis of the oxo ester (not isolated) to give the acetylpyridines. Com. pyridine aldehydes were purified by passing SO₂ into 50 g. aldehyde in 250 ml. O-free H₂O to complete precipitation of the adduct. The adduct was refluxed under N in 200 ml. 17% HCl to complete solution, neutralized with NaHCO₃, and extracted with Et₂O. The extracts were dried and distilled under N. The com. 2-, and 3-(hydroxymethyl)pyridines were purified by fractional distillation In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0SDS of cas: 27876-24-0).

4-Hexylpyridine (cas: 27876-24-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol� in pyridine vs. 150 kJ·mol� in benzene). Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.SDS of cas: 27876-24-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem