24564-83-8Relevant articles and documents
Discovery of memantyl urea derivatives as potent soluble epoxide hydrolase inhibitors against lipopolysaccharide-induced sepsis
Bao, Xuefei,Chen, Guoliang,Du, Fangyu,Hammock, Bruce D.,Liu, Qiu,Liu, Zhongbo,Morisseau, Christophe,Sun, Wenjiao,Wang, Chao,Xiao, Wei,Yang, Hao,Zhang, Tan,Zhou, Jun
, (2021/07/06)
Sepsis, a systemic inflammatory response, caused by pathogenic factors including microorganisms, has high mortality and limited therapeutic approaches. Herein, a new soluble epoxide hydrolase (sEH) inhibitor series comprising a phenyl ring connected to a
The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation
Li, Shanshan,Song, Gao,Wang, Liang-Liang,Weng, Zhiying,Xu, Guowei,Yang, Weimin,Yang, Yanming,Yang, Yaqing,Zhang, Jiajun,Zuo, Zhili
supporting information, (2020/02/27)
Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.
Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation
Hosseini-Sarvari, Mona,Koohgard, Mehdi,Firoozi, Somayeh,Mohajeri, Afshan,Tavakolian, Hosein
supporting information, p. 6880 - 6888 (2018/05/04)
A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.
Three-Component Synthesis of Quinolines Based on Radical Cascade Visible-Light Photoredox Catalysis
Choi, Jun-Ho,Park, Cheol-Min
supporting information, p. 3553 - 3562 (2018/09/22)
Synthesis of highly substituted quinolines has been developed based on three-component radical cascade based on visible-light photoredox catalysis. This tandem coupling reaction has been coordinated to proceed with high chemoselectivity based on the differential electronic properties of coupling partners. Subjection of electron-rich β-aminoacrylates with electron-deficient halides and alkenes to the optimized conditions leads to the formation of quinolines in good yields after in situ oxidation of tetrahydroquinolines. Detailed mechanistic studies which reveal an unexpected reaction pathway is described. (Figure presented.).
Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds
Firoozi, Somayeh,Hosseini-Sarvari, Mona,Koohgard, Mehdi
supporting information, p. 5540 - 5549 (2019/01/03)
Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.
Chemical reactivity and antimicrobial activity of N-substituted maleimides
Salewska, Natalia,Boros-Majewska, Joanna,Lcka, Izabela,Chylinska, Katarzyna,Sabisz, Michal,Milewski, Slawomir,Milewska, Maria J.
scheme or table, p. 117 - 124 (2012/04/18)
Several N-substituted maleimides containing substituents of varying bulkiness and polarity were synthesised and tested for antimicrobial and cytostatic activity. Neutral maleimides displayed relatively strong antifungal effect minimum inhibitory concentrations (MICs in the 0.54 g ml-1 range); their antibacterial activity was structure dependent and all were highly cytostatic, with IC50 values below 0.1 g ml-1. Low antimicrobial but high cytostatic activity was noted for basic maleimides containing tertiary aminoalkyl substituents. Chemical reactivity and lipophilicity influenced antibacterial activity of neutral maleimides but had little if any effect on their antifungal and cytostatic action. N-substituted maleimides affected biosynthesis of chitin and β(1,3)glucan, components of the fungal cell wall. The membrane enzyme, β(1,3)glucan synthase has been proposed as a putative primary target of N-ethylmaleimide and some of its analogues in Candida albicans cells.
Synthesis and fluorescent properties of model compounds for conjugated polymer containing maleimide units at the main chain
Onimura, Kenjiro,Matsushima, Mieko,Nakamura, Munetoshi,Tominaga, Tatsuya,Yamabuki, Kazuhiro,Oishi, Tsutomu
scheme or table, p. 3550 - 3558 (2012/05/19)
2,3-Diaryl substituted maleimides as model compounds of conjugated maleimide polymers [poly(RMI-alt-Ar) and poly(RMI-co-Ar)] were synthesized from 2,3-dibromo-N-substituted maleimide (DBrRMI) [R= cyclohexyl (DBrCHMI) and n-hexyl (DBrHMI)] and aryl boronic acid using palladium catalysts. To clarify structures of conjugated polymer containing maleimide units at the main chain, 13C NMR spectra of 2-aryl or 2,3-diaryl substituted maleimides were compared with those of N-substituted maleimide polymers. Copolymers obtained with DBrRMI via Suzuki-Miyaura cross-coupling polymerizations or Yamamoto coupling polymerizations were dehalogenated structures at the terminal end. This dehalogenation may contribute to the low polymerizability of DBrRMIs. On the other hand, the π-conjugated compounds showed high solubility in common organic solvents. The N-substituents of maleimide cannot significantly affect the photoluminescence spectra of 2,3-diaryl substituted maleimides derivatives. The fluorescence spectra of poly(RMI-alt-Ar) and poly(RMI-co-Ar) varied with N-substituents of the maleimide ring. When exposed to ultraviolet light of wavelength 352 nm, a series of 1,4-phenylene- and/or 2,5-thienylene-based copolymers containing N-substituted maleimide derivatives fluoresced in a yellow to blue color. It was found that photoluminescence emissions and electronic state of π-conjugated maleimide derivatives were controlled by aryl- and N-substituents, and maleimide sequences of copolymers.
A facile synthesis of N-substituted maleimides
Deshpande, Sunita R.,Maybhate, Shailaja P.,Likhite, Anjali P.,Chaudhary, Preeti M.
body text, p. 487 - 488 (2010/10/18)
A simple and efficient method for the synthesis of N-substituted maleimides from the corresponding maleamic acids under the phase transfer catalysis has been described.
Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides
Song, Hong Y.,Ngai, Mun H.,Song, Zhen Y.,MacAry, Paul A.,Hobley, Jonathan,Lear, Martin J.
experimental part, p. 3400 - 3406 (2010/01/06)
The cellular tracking, detection and sensing of protein or antibody movement are important aspects to advance our understanding of biomolecular interactions and activity. Antibodies modified with fluorescent dyes are also valuable tools, especially in immunology research. We describe here a proof-of-principle study of a new water-soluble coumarin probe with a maleimide thiol-reacting unit to fluorescently tag biomolecules. Highlights include: (1) a convenient water-based preparation of N-substituted maleimides, (2) a one-pot preparation of activated maleimido-esters, and (3) a bio-conjugation protocol for the selenol-promoted reduction of native disulfide bonds and the 'site-specific' labelling of antibodies with no significant loss of activity.
