29114-51-0Relevant academic research and scientific papers
8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
Xing, Gang,Zhi, Zhengxing,Yi, Ce,Zou, Jitian,Jing, Xuefeng,Yiu-Ho Woo, Anthony,Lin, Bin,Pan, Li,Zhang, Yuyang,Cheng, Maosheng
, (2021/07/19)
β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.
Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents
Choi, Hyunsuk,Ham, So-Young,Cha, Eunji,Shin, Yujin,Kim, Han-Shin,Bang, Jeong Kyu,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo
, p. 9821 - 9837 (2017/12/26)
Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.
Iridium(I) N-Heterocyclic Carbene (NHC)/Phosphine Catalysts for Mild and Chemoselective Hydrogenation Processes
Kerr, William J.,Mudd, Richard J.,Brown, Jack A.
, p. 4738 - 4742 (2016/04/05)
The directed chemoselective hydrogenation of olefins has been established by using iridium(I) catalysts, which feature a tuned NHC/phosphine ligand combination. This selective reduction process has been demonstrated in a wide array of solvents, including more environmentally acceptable media, also allowing further refinement of hydrogenation selectivity. The directed, chemoselective hydrogenation of olefins has been established by using iridium(I) catalysts, which feature a tuned NHC/phosphine ligand combination. This selective reduction process has been demonstrated in a wide array of solvents, including more environmentally acceptable media, also allowing further refinement of hydrogenation selectivity.
Iridium(I)-catalyzed regioselective C-H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality
Kerr, William J.,Mudd, Richard J.,Paterson, Laura C.,Brown, Jack A.
supporting information, p. 14604 - 14607 (2015/03/04)
Isotopic labelling is a key technology of increasing importance for the investigation of new C-H activation and functionalization techniques, as well as in the construction of labelled molecules for use within both organic synthesis and drug discovery. Herein, we report for the first time selective iridium-catalyzed C-H activation and hydrogen-isotope exchange at the β-position of unsaturated organic compounds. The use of our highly active [Ir(cod)(IMes)(PPh3)][PF6] (cod = 1, 5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective β-activation and labelling of a range of α, β-unsaturated compounds with differing steric and electronic properties. This new process delivers high levels of isotope incorporation over short reaction times by using low levels of catalyst loading.
Malononitrile-assisted highly chemoselective bismuth triflate catalyzed conjugate reduction of α,β-unsaturated ketones
Shang, Jun-Yan,Li, Fei,Bai, Xing-Feng,Jiang, Jian-Xiong,Yang, Ke-Fang,Lai, Guo-Qiao,Xu, Li-Wen
supporting information; scheme or table, p. 2809 - 2815 (2012/06/18)
A very simple, direct, bismuth-catalyzed conjugate reduction protocol that allows for the catalytic regioselective formation of substituted ketones from enones under mild conditions has been developed. We have shown for the first time that the combined poly(methylhydro)siloxane-malononitrile system can serve as an efficient reductant/reagent in 1,4-conjugate reduction of enones. The regioselectivity, efficiencies, and experimental simplicity of the present method complements the more complex methods previously employed in copper or palladium-catalyzed reduction. This method should prove attractive because of its mild reaction conditions and the interesting chemistry of combining the use of poly(methylhydro)siloxane and malononitrile for selective reduction. Copyright
Tandem β-boration/arylation of α,β-unsaturated carbonyl compounds by using a single palladium complex to catalyse both steps
Bonet, Amadeu,Gulyas, Henrik,Koshevoy, Igor O.,Estevan, Francisco,Sanau, Mercedes,Ubeda, M. Angeles,Fernandez, Elena
supporting information; experimental part, p. 6382 - 6390 (2010/08/03)
Diphenyl(3-methyl-2-indolyl)phosphine (C9H8NPPh 2, 1) gives stable dimeric palladium(II) complexes that contain the phosphine in P,Nbridging coordination mode. On treating 1 with [Pd(O 2CCH3)2], the new complexes [Pd(μ-C 9H7NPPh2)-(NCCH3)]2 (2) or [Pd(μ-C9H7NPPh2)-(μ-O 2CCH3)]2 (3) were isolated, depending on the solvent used, acetonitrile or toluene, respectively. Further reaction of 3 with the ammonium salt of 1 led to the substitution of one carboxylate ligand to afford [Pd(u-C9H7NPPh2)3(μ-O 2CCH3)] (4), in which the bimetallic unit is bonded by three C9H7NPPh2- moieties and one carboxylate group. Using this methodology, [Pd2(μ-C 6H4PPh2)2(μ-C9H 7NPPh2)(μ-O2CCX3)] (X = H (7); J. = F (8)) were synthesised from the ortho-metalated compounds [Pd(C 6H4PPh2)(μO2CCX3)], (X = H (5); J. = F (6)). Complexes 3, 4, 7, and 8 have been found to be active in the catalytic β-boration of α,β-unsaturated esters and ketones under mild reaction conditions. Hindrance of the carbonyl moiety has an influence on the reaction rate, but quantitative conversion was achieved in many cases. More remarkably, when aryl bromides were added to the reaction media, complex 7 induced a highly successful consecutive β-boration/crosscoupling reaction with dimethyl acrylamide as the substrate (99% conversion, 89 % isolated yield).
Enantioselective α-arylation of aldehydes via organo-SOMO catalysis. An ortho-selective arylation reaction based on an open-shell pathway
Conrad, Jay C.,Kong, Jongrock,Laforteza, Brian N.,MacMillan, David W. C.
supporting information; experimental part, p. 11640 - 11641 (2009/12/08)
(Chemical Equation Presented) The intramolecular-arylation of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3π-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective reaction with an array of pendent electron-rich aromatics and heterocycles thus efficiently providing cyclic α-aryl aldehyde products (10 examples: ≥70% yield and ≥90% ee). In accordance with our radical mechanism, when there is a choice between arylation at the ortho or para position of anisole substrates, we find that arylation proceeds selectively at the ortho position.
NOVEL THIENOPYRIMIDINE DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
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, (2010/11/28)
The present invention relates to a novel thienopyrimidine derivative having an excellent anti? inflammatory and anti-cancer activity, or a pharmaceutically acceptable salt thereof, a process for the preparation thereof and a pharmaceutical composition comprising the same. The compound according to the present invention strongly inhibits IKB kinase-β (IKK-β) involved in the activation of a transcriptional factor, NF-κB, which is associated with inducing various immune and inflammatory diseases, whereby a composition comprising the compound is a useful therapeutic agent against inflammatory diseases, in particular, arthritis and cancer.
Synthesis of Quinolines and 2H-Dihydropyrroles by Nucleophilic Substitution at the Nitrogen Atom of Oxime Derivatives
Kitamura, Mitsuru,Yoshida, Masayuki,Kikuchi, Takashi,Narasaka, Koichi
, p. 2415 - 2426 (2007/10/03)
Isomerization of oxime derivatives was researched in detail to find out the methods for the syn-anti isomerization of O-substituted oximes. Based on these findings were developed simple methods for the preparation of aza-heterocycles from both stereoisomers of oximes. Quinolines were synthesized from β-aryl ketone oximes by treatment with trifluoroacetic anhydride and 4-chloranil. γ,δ-Unsaturated O-methoxyacetyloximes were transformed to 2H-dihydropyrroles by reaction with methoxy-acetic acid.
Room-temperature ionic liquids as new solvents for organic electrosynthesis. The first examples of direct or nickel-catalysed electroreductive coupling involving organic halides
Barhdadi, Rachid,Courtinard, Coralie,Nedelec, Jean Yves,Troupel, Michel
, p. 1434 - 1435 (2007/10/03)
Direct or Ni-catalysed electroreductive homocouplings of organic halides and couplings of organic halides with activated olefins are efficiently conducted by constant current electrolyses in an undivided cell in room-temperature ionic liquids as the solvent-electrolyte media.
