Tag: 200-300

Structure-Activity Relationships and X-ray Structures Describing the Selectivity of Aminopyrazole Inhibitors for c-Jun N-terminal Kinase 3 (JNK3) over p38 was written by Kamenecka, Ted;Habel, Jeff;Duckett, Derek;Chen, Weimin;Ling, Yuan Yuan;Frackowiak, Bozena;Jiang, Rong;Shin, Youseung;Song, Xinyi;LoGrasso, Philip. And the article was included in Journal of Biological Chemistry in 2009.HPLC of Formula: 89978-52-9 This article mentions the following:

C-Jun N-terminal kinase 3浼? (JNK3浼?) is a mitogen-activated protein kinase family member expressed primarily in the brain that phosphorylates protein transcription factors, including c-Jun and activating transcription factor-2 (ATF-2) upon activation by a variety of stress-based stimuli. In this study, we set out to design JNK3-selective inhibitors that had >1000-fold selectivity over p38, another closely related mitogen-activated protein kinase family member. To do this we employed traditional medicinal chem. principles coupled with structure-based drug design. Inhibitors from the aminopyrazole class, such as SR-3576, were found to be very potent JNK3 inhibitors (IC₅₀ = 7 nM) with >2800-fold selectivity over p38 (p38 IC₅₀ > 20 娓璏) and had cell-based potency of 閳? 娓璏. In contrast, indazole-based inhibitors exemplified by SR-3737 were potent inhibitors of both JNK3 (IC₅₀ = 12 nM) and p38 (IC₅₀ = 3 nM). These selectivity differences between the indazole class and the aminopyrazole class came despite nearly identical binding (root mean square deviation = 0.33 鑴? of these two compound classes to JNK3. The structural features within the compounds giving rise to the selectivity in the aminopyrazole class include the highly planar nature of the pyrazole, N-linked Ph structures, which better occupied the smaller active site of JNK3 compared with the larger active site of p38. In the experiment, the researchers used many compounds, for example, Ethyl 2-bromoisonicotinate (cas: 89978-52-9HPLC of Formula: 89978-52-9).

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. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.HPLC of Formula: 89978-52-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A new synthesis of symmetrical 2,5-disubstituted 1,3,4-oxadiazoles was written by Bentiss, Fouad;Lagrenee, Michel. And the article was included in Journal of Heterocyclic Chemistry in 1999.Name: 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole This article mentions the following:

Title compounds I [R = (un)substituted phenyl; 2-, 3-, 4-pyridinyl; 2-thienyl] were prepared in good yields by reaction of aromatic acids with hydrazine dihydrochloride in a mixture of orthophosphoric acid, phosphorus pentoxide and, in general, with addition of phosphorus oxychloride to the reaction mixture In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Name: 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. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the 锜?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 锜?bonds. 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. Name: 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

An efficient conversion of alcohols to alkyl bromides using pyridinium based ionic liquids: a green alternative to appel reaction was written by Das, Pranab J.;Das, Jupitara;Das, Dimpee. And the article was included in Asian Journal of Chemistry in 2018.Formula: C10H16BrN This article mentions the following:

Pyridinium based ionic liquids namely 4-alkylpyridinium bromides were prepared and used for the conversion of alcs. to alkyl bromides in the presence of p-toluenesulfonic acid in the absence of volatile organic compounds This solvent free procedure promises to be a much improved and environmentally benign alternative to the Appel reaction. 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. Pyridine is diamagnetic and has a diamagnetic susceptibility of 閳?8.7 鑴?10閳? cm3璺痬ol閳?.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ璺痬ol閳? in the liquid phase and 140.4 kJ璺痬ol閳? 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.Formula: C10H16BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Comparative study of the retention of pyridinium and imidazolium based ionic liquids on octadecylsilica stationary phase under ion pairing mechanism with alkylsulphonate anions was written by Radulescu, Medeea;Iorgulescu, Emilia-Elena;Mihailciuc, Constantin;David, Victor. And the article was included in Revue Roumaine de Chimie in 2012.Application of 65350-59-6 This article mentions the following:

Retention data for several pyridinium and imidazolium ionic liquids in presence of alkylsulfonates (C6, C7 and C8) were used in studying the retention of these cations on the octadecylsilica surface. This study showed that ionic liquids can be adsorbed on octadecylsilica surface, due to the polar interactions with the residual silanols from surface of stationary phase and hydrophobic interactions between hydrophobic moiety of these cations and octadecyl chains from the surface of the stationary phase. An unusual chromatog. retention behavior has been observed: the functional dependencies between the logarithm of the retention factor (k) and the methanol content in the mobile phase followed a binomial pattern (U-shaped), with a min. positioned within the interval 60-75% methanol. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Application of 65350-59-6).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) belongs to pyridine derivatives. Pyridine has a conjugated system of six 锜?electrons that are delocalized over the ring. The molecule is planar and, thus, follows the H鐪塩kel criteria for aromatic systems. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C閳ユ弻 in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Application of 65350-59-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Hydroarylation of Arenes via Reductive Radical-Polar Crossover was written by Flynn, Autumn R.;McDaniel, Kelly A.;Hughes, Meredith E.;Vogt, David B.;Jui, Nathan T.. And the article was included in Journal of the American Chemical Society in 2020.Name: tert-Butyl (3-bromopyridin-4-yl)carbamate This article mentions the following:

A photocatalytic system for the dearomative hydroarylation of benzene derivatives has been developed. Using a combination of an organic photoredox catalyst and an amine reductant, this process operates through a reductive radical-polar crossover mechanism where aryl halide reduction triggers a regioselective radical cyclization event, followed by anion formation and quenching to produce a range of complex spirocyclic cyclohexadienes. This light-driven protocol functions at room temperature in a green solvent system (aqueous MeCN) without the need for precious metal-based catalysts or reagents or the generation of stoichiometric metal byproducts. In the experiment, the researchers used many compounds, for example, tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9Name: tert-Butyl (3-bromopyridin-4-yl)carbamate).

tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the 锜?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 锜?bonds. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Name: tert-Butyl (3-bromopyridin-4-yl)carbamate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Structural analysis of mono-substituted N-butyl-pyridinium salts: in search of ionic liquids was written by Kelley, Steven P.;Smetana, Volodymyr;Mudring, Anja-Verena;Rogers, Robin D.. And the article was included in Journal of Coordination Chemistry in 2021.Application In Synthesis of 1-Butyl-4-methylpyridin-1-ium bromide This article mentions the following:

Four mono-substituted N-butylpyridinium salts, 1-butyl-4-dimethylaminopyridinium chloride [b4dmapy]Cl, 1-butyl-4-methylpyridinium bromide [b4mpy]Br, 1-butyl-4-methylpyridinium hexafluorophosphate [b4mpy][PF₆], and 1-butyl-3-methylpyridinium hexafluorophosphate [b3mpy][PF₆] were synthesized and characterized using single crystal x-ray diffraction. The crystal structures were examined with the intent of identifying ion interactions leading to higher m.ps. of the halide salts with respect to the [PF₆]^– salts. The changes in hydrogen bonding, C-H璺矾璺熀, and van der Waals interactions were analyzed with respect to anion, functional groups, and the symmetry of the cation to establish interdependence with the compound’s physicochem. properties. The cation-anion interactions are represented by highly directional hydrogen bonds and show strong preference to positions of interaction depending on the anion. The cations of the halide salts show strong tendency towards higher dimensional formations, while those of the [PF₆]^– salts prefer low dimensional assemblies both being based mainly on the weaker van der Waals interactions. These interactions depend on the shape of the cation but may offer certain structure-ordering rigidity accommodating variable anions. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Application In Synthesis of 1-Butyl-4-methylpyridin-1-ium bromide).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) 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, 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. Application In Synthesis of 1-Butyl-4-methylpyridin-1-ium bromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Enantioselective synthesis of trifluoromethyl substituted piperidines with multiple stereogenic centers via hydrogenation of pyridinium hydrochlorides was written by Chen, Mu-Wang;Ye, Zhi-Shi;Chen, Zhang-Pei;Wu, Bo;Zhou, Yong-Gui. And the article was included in Organic Chemistry Frontiers in 2015.Computed Properties of C6H3BrF3N This article mentions the following:

An enantioselective iridium-catalyzed hydrogenation of trifluoromethyl substituted pyridinium hydrochlorides is described. Introduction of a trifluoromethyl group increases the reactivity due to the electron-withdrawing effect. Three stereogenic centers could be generated in one operation. This methodol. provides a convenient route to chiral poly-substituted piperidines I (R = Me, Et; Ar = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 2-naphthyl, etc.) and II (Ar = Ph, 4-CF₃C₆H₄, 3,5-F₂C₆H₃, 1-naphthyl) with up to 90% ee. In the experiment, the researchers used many compounds, for example, 2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0Computed Properties of C6H3BrF3N).

2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0) 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, 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. Computed Properties of C6H3BrF3N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Action of pyridine N-oxide and of the picoline N-oxides on 2-bromopyridine. Oxidative brominations with pyridine N-oxide hydrobromide was written by Ramirez, Fausto;Von Ostwalden, P.. And the article was included in Chemistry & Industry (London, United Kingdom) in 1957.SDS of cas: 13472-81-6 This article mentions the following:

2-BrC₅H₄N (I) and pyridine 1-oxide (II) at 100鎺?give, after a 2-hr. induction period, C₅H₅N, N-(2-pyridyl)-2-pyridone (III), and the 3-Br derivative (IV) of III, m. 129鎺?(obtained but not identified by Takeda, et al., C.A. 47, 8071a). The presence of HBr eliminates the induction period and also leads to the formation of addnl. products, such as the 3,5-di-Br derivative (V) of III, m. 158鎺? and 2,5-dibromo-2-pyridone, m. 207鎺? IV and V are formed from III by oxidative bromination. A mixture of III and the HBr salt of II gives at 200鎺?IV, C₅H₅N, and some V. With PhMe as moderator and HBr as initiator, I + II give little or no brominated products. Similarly, 3-picoline N-oxide yields the N-(5-methyl-2-pyridyl) analog of III, m. 94鎺? and of IV, m. 152鎺? 4-picoline N-oxide gives the N-(4-methyl-2-pyridyl) analog of III, m. 114鎺? 2-picoline N-oxide, the N-(6-methyl-2-pyridyl) analog, m. 42鎺? Thus a heterocyclic N-oxide can act both as reagent and subsequently as substrate in nucleophilic attacks. The position of Br in IV was proved by bromination of III with 1 mole Br to IV, and comparison with authentic 5-Br derivative of III (m. 134鎺? synthesized from 5-bromo-2-pyridone and I. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6SDS of cas: 13472-81-6).

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. SDS of cas: 13472-81-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pd-Catalyzed regio- and enantioselective allylic substitution with 2-pyridones was written by Khan, Sardaraz;Shah, Babar Hussain;Khan, Ijaz;Li, Meiqi;Zhang, Yong Jian. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2019.Quality Control of 3,5-Dibromo-2-hydroxypyridine This article mentions the following:

An efficient method for the asym. synthesis of N-substituted 2-pyridones via Pd-catalyzed regio- and enantioselective allylic substitution of hydroxyl-containing allylic carbonates with 2-pyridones were developed. By using a palladium complex in-situ generated from Pd₂(dba)₃璺疌HCl₃ and phosphoramidite as a ligand, the process allowed rapid access to N-substituted 2-pyridones with complete chemo- and regioselectivities and good to high enantioselectivities. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6Quality Control of 3,5-Dibromo-2-hydroxypyridine).

3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ璺痬ol閳? in pyridine vs. 150 kJ璺痬ol閳? in benzene). Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Quality Control of 3,5-Dibromo-2-hydroxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The chemistry of 1,3,4-oxadiazoles with regard to the chemotherapy of tuberculosis was written by Novotny, A.;Brezik, Z.;Pridal, J.;Kalfus, K.. And the article was included in Cesko-Slovenska Farmacie in 1958.Synthetic Route of C12H8N4O This article mentions the following:

2-(4-Pyridyl)-4,5-dihydro-1,3,4-oxadiazol-5-one (I) was prepared by the action of COCl₂ on isonicotinic acid hydrazide (II) at 0-5鎺?according to Lieser and Nischk (C.A. 44, 3979h), U.S. 2,665,279 (C.A. 49, 2521g), and Ger. 923,722 (C.A. 51, 12983c), in 90% yield, m. 275.9-6.1鎺?(hot water). Similarly was prepared from NCCH₂CONHNH₂ (III) and COCl₂ 88% 2-cyanomethyl-4,5-dihydro-1,3,4-oxadiazol-5-one (IV), m. 162.2-2.3鎺?(EtOH). A new procedure is described for the preparation of N¹N²-diacylhydrazines. II (13.7 g.) mixed with 29.1 mL. 80% HCO₂H, allowed to stand 8 h. at laboratory temperature, evaporated in vacuo, and the residue crystallized from 235 mL. AcOBu yielded 83% N¹-formyl-N²isonicotinoylhydrazine, m. 141.2-1.7鎺? Similarly were prepared: N¹-formyl-N²-cyanohydrazine, m. 153.2-3.8鎺?(EtOH); N¹-acetyl-N²-isonicotinoylhydrazine (V) from II, water, and AcOAc, m. 162.2-2.5鎺?(AcOBu); N¹propionyl-N²-isonicotinoylhydrazine, m. 130.2-0.4鎺?(AcOBu); N¹-butyryl-N²-isonicotinoyl-hydrazine, m. 140.1-0.3鎺?(2:1 AcOBu-C₅H₅N). 2-Alkyl-5-(4-pyridyl)-1,3,4-oxadiazoles were prepared by the modified method of McMillan, et al. (C.A. 48, 11413h). V (5.37 g.) and 5 g. P₂O₅ heated with stirring to 100-30鎺? the resulting product dissolved after cooling in 100 mL. water and pH simultaneously made to 8-9 with Na₂CO₃, the solution evaporated, dried, the residue extracted 4 h. with C₅H₅N in a Soxhlet apparatus, the excess solution evaporated, and crystallized 15 h. at 4鎺?yielded 26% 2-methyl-5-(4-pyridyl)-1,3,4-oxadiazole, m. 150.5-1.0鎺?(boiling EtOH). Similarly was prepared 29% 2-Et derivative m. 58.0-8.5鎺?(EtOH), while the synthesis of the 2-Pr derivative and 2-(4-pyridyl)-1,3,4-oxadiazole was not successful. Dehydration was also achieved by heating with high boiling ethers (Ph₂O) to 250-70鎺?and by azeotropic dehydration (25-30% yields). Bacteriol. tests showed a high tuberculostatic effect in vivo of I (similar to II) and IV (similar to III), while 2-alkyl-5-(4-pyridyl)-1,3,4-oxadiazoles showed in vitro only a low activity. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Synthetic Route of C12H8N4O).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) 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. Pyridine derivatives are also useful as small-molecule 浼?helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Synthetic Route of C12H8N4O

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem