Category: pyridine-derivatives

Kuwata, Yoshiyuki; Sonoda, Motohiro; Tanimori, Shinji published the artcile< Facile Synthesis of Phenanthridinone Alkaloids via Suzuki-Miyaura Cross-coupling>, Electric Literature of 53636-56-9, the main research area is phenanthridinone alkaloid crinasiadine dihydrobicolorine trisphaeridine bicolorine facile synthesis; aminophenylboronic acid Suzuki Miyaura cross coupling bromobenzoate bromoheteroarenecarboxylate.

Phenanthridinone alkaloids crinasiadine (I) and N-alkylcrinasiadines II [R = CH2CH2CHMe2, CH2CH2CO2Et, CH2CH2Ph, CH2CH2CH2CO2Et] have been synthesized based on palladium-catalyzed tandem C-C and C-N bond formation starting from 2-aminophenylboronic acid and 2-bromobenzoate in short steps. Related alkaloids, 5,6-dihydrobicolorine (III), trisphaeridine (IV), and bicolorine (V) have also been synthesized.

Journal of Heterocyclic Chemistry published new progress about Alkaloids Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (phenanthridine). 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Electric Literature of 53636-56-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Singh, Malvinder P.; Bathini, Yadagiri; Lown, J. William published the artcile< Site selective alkoxymethylation of imidazo[4,5-b]pyridines: structural analysis by high field NMR methods>, Product Details of C6H7N3O2, the main research area is alkylation alkoxymethylation imidazopyridine regiochem; aryl imidazopyridine preparation structure; tautomer nucleophile alkoxymethylation regiochem imidazopyridine; solvent effect alkoxymethylation benzimidazole methoxyphenyl; benzimidazole alkoxymethyl methoxyphenyl mol structure; mol structure alkoxymethyl methoxyphenyl imidazopyridine.

The alkylation reactions of 2-aryl-1(3)H-imidazo[4,5-b]pyridines (equivalent to 1-deazapurines) with alkoxymethyl chlorides and bromoacetonitrile are described. The structural assignments of the products were made using 2-dimensional 1H-1H NOE (NOESY) and selective INEPT (INAPT) 13C NMR experiments using polarization transfer from C-bound hydrogens in the alkyl side chains to selected 13C resonances via long-range 3JCH couplings. Although 3 isomeric N-alkyl derivatives could arise from a single heterocycle based on considerations of tautomeric equilibrium, however, the reactions exhibit marked site selectivity even under quite different reaction conditions. Thus, N-3 alkyl derivatives are produced exclusively in basic (Et3N/NaH) nonpolar media following an SEE2cB mechanism. Solvent effects are evident in a loss of N-3 vs. N-1 selectivity for alkylation when the polar aprotic solvent DMF is used. Under neutral conditions direct alkylation occurs at the N-4 position following an SE2′ mechanism. The overall site selectivity appears to be governed by the relative reactivity of individual nucleophilic sites rather than the tautomeric composition in solution The regioselective alkoxymethylation of 2-(4-methoxyphenyl)benzimidazole, and methyl-2-(4-methoxyphenyl)imidazopyridines I (R = hydrogen, methyl; X = CH, N) were reported. Bis(imidazo[4,5-b]pyridine analogs of Hoechst 33258 were prepared

Heterocycles published new progress about Molecular structure. 21901-29-1 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Product Details of C6H7N3O2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ngo, Khang; Collins-Kautz, Chelsey; Gerstenecker, Stefan; Wagner, Bjoern; Heine, Andreas; Klebe, Gerhard published the artcile< Protein-Induced Change in Ligand Protonation during Trypsin and Thrombin Binding: Hint on Differences in Selectivity Determinants of Both Proteins?>, Product Details of C6H8N2, the main research area is Protein Induced ligand protonation trypsin thrombin.

Trypsin and thrombin, structurally similar serine proteases, recognize different substrates; thrombin cleaves after Arg, whereas trypsin cleaves after Lys/Arg. Both recognize basic substrate headgroups via Asp189 at the bottom of the S1 pocket. By crystallog. and isothermal titration calorimetry (ITC), we studied a series of D-Phe/D-DiPhe-Pro-(amino)pyridines. Identical ligand pairs show the same binding poses. Surprisingly, one ligand binds to trypsin in protonated state and to thrombin in unprotonated state at P1 along with differences in the residual solvation pattern. While trypsin binding is mediated by an ordered water mol., in thrombin, water is scattered over three hydration sites. Although having highly similar S1 pockets, our results suggest different electrostatic properties of Asp189 possibly contributing to the selectivity determinant. Thrombin binds a specific Na+ ion next to Asp189, which is absent in trypsin. The electrostatic properties across the S1 pocket are further attenuated by charged Glu192 at the rim of S1 in thrombin, which is replaced by uncharged Gln192 in trypsin.

Journal of Medicinal Chemistry published new progress about Enzyme functional sites, active. 3731-53-1 belongs to class pyridine-derivatives, and the molecular formula is C6H8N2, Product Details of C6H8N2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Day, Jon I.; Singh, Kamaljeet; Trinh, Winston; Weaver, Jimmie D. published the artcile< Visible Light Mediated Generation of trans-Arylcyclohexenes and Their Utilization in the Synthesis of Cyclic Bridged Ethers>, Name: Ir(p-F-ppy)3, the main research area is visible light mediated generation trans arylcyclohexene; cyclic bridged ether preparation reaction mechanism hydrogen bonding.

While accessible via UV-irradiation of cis-cyclohexene, trans-cyclohexene has thus far been an investigation driven by curiosity, and due primarily to its short lifespan, has until recently not been employed for productive synthesis. Herein, we present straightforward conditions that provide access to a class of trans-arylcyclohexenes and demonstrate their utility in the formation of oxabicyclic ethers, which are otherwise inaccessible from the corresponding cis-cyclohexene. A key challenge to utilizing the incredible ca. 52 kcal/mol strain energy of trans-cyclohexene to drive synthesis was overcoming its short lifetime. Herein, we show that preorganization via hydrogen bonding between the substrate and the reaction partner prior to isomerization is a viable strategy to overcome the inherently short lifetime of trans-cyclohexene.

Journal of the American Chemical Society published new progress about Bridged bicyclic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 370878-69-6 belongs to class pyridine-derivatives, and the molecular formula is C33H21F3IrN3, Name: Ir(p-F-ppy)3.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Tatikonda, Rajendhraprasad; Cametti, Massimo; Kalenius, Elina; Famulari, Antonino; Rissanen, Kari; Haukka, Matti published the artcile< Mononuclear Ru(II) PolyPyridyl Water Oxidation Catalysts Decorated with Perfluoroalkyl C8H17-Tag Bearing Chains>, Application In Synthesis of 1762-41-0, the main research area is mononuclear ruthenium polypyridyl complex preparation crystal mol structure; water oxidation catalyst decorated perfluoroalkyl polypyridyl mononuclear ruthenium complex; perfluoroundecyl polypyridyl ruthenium complex preparation crystal mol structure.

A set of novel polypyridyl Ru(II) complexes 1-7, decorated with one, two or three C8F17 tags have been synthesized and characterized by NMR, UV/Vis spectroscopy and, in the case of series of complexes 1-3, 5 and 7 by x-ray diffraction on single crystals. Solid state structures of 3, 5 and 7 were also subjected to computational DFT study in order to gain insights into the effect of a different number of perfluorinated tags on their stability in the solid-state. The complexes are stable in solution under strongly oxidative conditions, do keep catalytic activity in their aquo forms (1′-7′) comparing well with parent complex 8′, and their amphiphilic nature could allow for their incorporation in fluorous media and interfaces.

European Journal of Inorganic Chemistry published new progress about Crystal structure. 1762-41-0 belongs to class pyridine-derivatives, and the molecular formula is C10H6Cl2N2, Application In Synthesis of 1762-41-0.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Huang, Zhi; Zhou, Wei; Li, Yongtao; Cao, Mei; Wang, Tianqi; Ma, Yakun; Guo, Qingxiang; Wang, Xin; Zhang, Chao; Zhang, Chenglan; Shen, Wenzhi; Liu, Yanhua; Chen, Yanan; Zheng, Jianyu; Yang, Shengyong; Fan, Yan; Xiang, Rong published the artcile< Novel hybrid molecule overcomes the limited response of solid tumours to HDAC inhibitors via suppressing JAK1-STAT3-BCL2 signalling>, Reference of 220731-04-4, the main research area is breast ovarian cancer HDAC inhibitor JAK1 STAT3 BCL2 signaling; CDK4/6; HDAC1; JAK1; inhibitor; solid tumour.

Despite initial progress in preclin. models, most known histone deacetylase inhibitors (HDACis) used as a single agent have failed to show clin. benefits in nearly all types of solid tumors. Hence, the efficacy of HDACis in solid tumors remains uncertain. Herein, we developed a hybrid HDAC inhibitor that sensitized solid tumors to HDAC-targeted treatment. Methods: A hybrid mol., Roxyl-zhc-84 was designed and synthesized with novel architecture. The pharmacokinetics and toxicity of Roxyl-zhc-84 were analyzed. Results: Roxyl-zhc-84 showed excellent pharmacokinetics and low toxicity. The novel hybrid inhibitor Roxyl-zhc-84 induced cell apoptosis and G1-phase arrest in breast cancer and ovarian cancer cell lines. In three mouse models, oral administration of Roxyl-zhc-84 led to significant tumor regression without obvious toxicity. Moreover, Roxyl-zhc-84 dramatically improved the limited response of traditional HDAC inhibitors in solid tumors via overcoming JAK1-STAT3-BCL2-mediated drug resistance. Roxyl-zhc-84 treatment exhibited vastly superior efficacy than the combination of HDAC and JAK1 inhibitors both in vitro and in vivo. Conclusion: Concurrent inhibition of HDAC and CDK using Roxyl-zhc-84 with addnl. JAK1 targeting resolved the limited response of traditional HDAC inhibitors in solid tumors via overcoming JAK1-STAT3-BCL2-mediated drug resistance, providing a rational multi-target treatment to sensitize solid tumors to HDACi therapy.

Theranostics published new progress about Acetylated histone H3 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 220731-04-4 belongs to class pyridine-derivatives, and the molecular formula is C10H15N3O2, Reference of 220731-04-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kumar, Sonu; Sarmah, Manash P.; Reddy, Yella; Bhatt, Ashish; Kant, Ravi published the artcile< A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles>, Electric Literature of 3731-53-1, the main research area is aryl benzoimidazole preparation; fluoronitrobenzene amine cyclization microwave irradiation; imidazopyridine aryl preparation; amine nitrofluoropyrdine cyclization microwave irradiation.

A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles were described. Mechanistically, the reaction proceeded by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation of N-hydroxy intermediate, which at higher temperature cleaved to afford the desired product. This approach achieved reductions in reaction times, higher yields, cleaner reactions than the previously described synthetic processes.

Synthetic Communications published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 3731-53-1 belongs to class pyridine-derivatives, and the molecular formula is C6H8N2, Electric Literature of 3731-53-1.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

El-Marrouki, Dalel; Touchet, Sabrina; Abdelli, Abderrahmen; M’Rabet, Hedi; Efrit, Mohamed Lotfi; Gros, Philippe C. published the artcile< Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor>, SDS of cas: 3731-53-1, the main research area is indole preparation; cinnoline preparation; diketone primary amine Michael; 1,4-diketone; N-heterocycle; cinnoline; indole; indolone.

A straightforward and metal-free strategy for the synthesis of nitrogen-containing heterocyclic moieties, indoles I [R1 = Me, Et; R2 = Bn, CH(Me)Ph, CH2(CH2)2NMe2, etc.], indolones II [R3 = Me, Et, Ph; R4 = Bn, 4-BrC6H4, 4-pyridylmethyl, etc.] and cinnolines III [R5 = Me, Ph, 2-thienyl, etc.; R6 = H, Me] was developed via Michael reaction 1,4-diketones and primary amines. The protocols developed here used mild conditions, were functional-group tolerant, transition-metal-free, proceeded in moderate to good yield.

Beilstein Journal of Organic Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 3731-53-1 belongs to class pyridine-derivatives, and the molecular formula is C6H8N2, SDS of cas: 3731-53-1.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kooyman, E. C.; Wibaut, J. P. published the artcile< Pyridine and quinoline derivatives. LX. The orientation of the CO2C2H5 group in the condensation product of malonic ester and β-aminocrotonic acid ester>, Product Details of C9H9Cl2NO2, the main research area is .

In the 2-methyl-4,6-dihydroxypyridinecarboxylate described by Knoevenagel and Fries (Ber. 31, 767(1898)), the position of the carboxylate group was unknown. The location of this group at 5 rather than at 3 was established by the following reactions: The original condensation product, heated with POCl3 at 120° in a sealed tube for 4 hrs., yielded a mixture of the acid chloride (I) and the Et ester (II) of 2-methyl-4,6-dichloro-5-pyridinecarboxylic acid, which could be separated by fractional distillation at 1 mm. The first fraction b. 97-104°, and after a 2nd distillation was obtained as a clear, colorless oil which solidified at 14.8°. The analyses agreed fairly well with C7H4ONCl3. On heating with H2O, HCl was split off, and the free acid was obtained. The compound was therefore believed to be I. The 2nd fraction b. 113-16°. It was obtained in 30% yield as white needles, m. 56° (50% EtOH), which were readily soluble in Et2O and EtOH, and sparingly soluble in H2O. It was identified as II. The free acid obtained from the ester by saponification m. 151.5° (dilute HCl) and was slightly soluble in H2O, very slightly soluble in HCl, but readily soluble in Et2O and EtOH. By catalytic reduction of II in absolute EtOH with Pd chloride and KOAc, the Cl was removed, and Et 2-methyl-5-pyridinecarboxylate (III) was obtained in 72% yield as a colorless oil b2 97° (Graf, C.A. 26, 1932). By saponification of III with KOH, preparation of the Cu salt, and decomposition with H2S, the free acid (IV) was obtained. It was purified by sublimation at 180°/35 mm. and m. 209-10°. It was identified by mixed m.p. with a sample prepared from 2-methyl-5-ethylpyridine. The amide (V), m. 196°, was prepared from III by shaking with NH3 according to the method of Graf. The picrate of the ester m. 170-1° (light yellow needles from alc. picric acid). The amide and the picrate showed no m.p. depression when mixed with the corresponding amide and picrate prepared from the ester obtained from 2-methyl-5-ethylpyridine.

Recueil des Travaux Chimiques des Pays-Bas et de la Belgique published new progress about 86129-63-7. 86129-63-7 belongs to class pyridine-derivatives, and the molecular formula is C9H9Cl2NO2, Product Details of C9H9Cl2NO2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

de Oliveira Silva, Juliana; Angnes, Ricardo A.; Menezes da Silva, Vitor H.; Servilha, Bruno M.; Adeel, Muhammad; Braga, Ataualpa A. C.; Aponick, Aaron; Correia, Carlos Roque D. published the artcile< Intermolecular Noncovalent Hydroxy-Directed Enantioselective Heck Desymmetrization of Cyclopentenol: Computationally Driven Synthesis of Highly Functionalized cis-4-Arylcyclopentenol Scaffolds>, SDS of cas: 1416819-91-4, the main research area is cyclopentenol aryldiazonium palladium chiral dihydrooxazole enantioselective Heck desymmetrization catalyst; arylcyclopentenol stereoselective preparation.

New computationally driven protocols for the Heck desymmetrization of 3-cyclopenten-1-ol with aryldiazonium tetrafluoroborates were developed. These new conditions furnished remarkable product selectivity originating from a resident hydroxyl group and the critical choice of the reaction solvent. Mechanistic insights gleaned from theor. calculations of the putative transition states predicted toluene as an adequate solvent choice to attain high enantioselectivity by strengthening the noncovalent interaction of the substrate hydroxyl group and the chiral cationic palladium catalyst. Laboratory experiments validated the theor. predictions, and by employing 2% MeOH/toluene as solvent, the Heck-Matsuda reaction provided exclusively the cis-4-arylcyclopentenols in good to excellent yields in enantiomeric excesses up to 99%. The performance of the new PyOx ligand (S)-4-tert-butyl-2-(3,5-dichloropyridin-2-yl)-4,5-dihydrooxazole was also successfully evaluated in the Heck-Matsuda desymmetrization of 3-cyclopenten-1-ol. The synthetic potential of these highly functionalized cis-4-arylcyclopentenols is illustrated by a gold-catalyzed synthesis of cyclopenta[b]benzofuran skeletons.

Journal of Organic Chemistry published new progress about Chiral ligands Role: CAT (Catalyst Use), SPN (Synthetic Preparation), USES (Uses), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, SDS of cas: 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem