21233-61-4Relevant articles and documents
Synthesis and antimycobacterial activities of ring-substituted quinolinecarboxylic acid/ester analogues. Part 1
Vaitilingam, Balasubramanian,Nayyar, Amit,Palde, Prakash B.,Monga, Vikramdeep,Jain, Rahul,Kaur, Sukhraj,Singh, Prati Pal
, p. 4179 - 4188 (2004)
Structural optimization of recently discovered new chemical entity, 2,8-dicyclopentyl-4-methylquinoline (DCMQ; MIC= 6.25μg/mL, M. tuberculosis H37Rv) resulted in the synthesis of four new series of ring-substituted quinolinecarboxylic acids/esters constit
Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes
Smyrnov, Vladyslav,Muriel, Bastian,Waser, Jerome
, p. 5435 - 5439 (2021/07/21)
We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.
Antiaging activity, molecular docking, and prediction of percutaneous absorption parameters of quinoline–hydrazone hybrids
Osorio, Edison,Bravo, Karent,Cardona, Wilson,Yepes, Andres,Osorio, Edison H.,Coa, Juan C.
, p. 1959 - 1973 (2019/09/03)
The application of antiaging agents can contribute to the prevention and control of skin photoaging. In the current research, nine quinoline–hydrazone hybrids were synthesized to obtain biologically active compounds as possible antiaging agents. The compounds were tested through a comprehensive in vitro evaluation of antielastase, anticollagenase, and antihyaluronidase activities along with the determination of their potential to quench reactive oxygen species (ROS) by the ORAC method. The selected hybrids were subsequently tested on human dermal fibroblasts (HDF) to reveal possible UVB photoprotective activity. The most potent antiaging protection of all the prepared compounds was shown by the trihydroxylated quinoline–hydrazones 5 and 9, which showed the best collagenase inhibition (IC50 = 39.4 and 45.6 μM, respectively). Compound 5 also showed activity against elastase and hyaluronidase (IC50 = 164.2 and 318.8 μM, respectively). The molecular docking results suggest that the difference of inhibition between 5 and 9 is principally attributed to the hydrogen bonds interactions in the residues His218 and His228, and Zn atom in collagenase, Val216 in elastase and Tyr75 in hyaluronidase. In addition, compounds 5 and 9 were able to significantly protect human skin cells from UVB radiation in vitro. These compounds significantly decreased UVB-induced MMP-1 and ROS production and inhibited the suppression of type I procollagen synthesis in cultured HDF. The in silico dermatopharmacokinetic parameters showed promising results. Therefore, our study presented promising results for antiaging drug discovery, focusing on quinoline–hydrazone hybrids as dual inhibitors of skin aging-related enzymes, antioxidants, and inhibitors of the biological effects of UVB irradiation.
Development of N-Doped Carbon-Supported Cobalt/Copper Bimetallic Nanoparticle Catalysts for Aerobic Oxidative Esterifications Based on Polymer Incarceration Methods
Yasukawa, Tomohiro,Yang, Xi,Kobayashi, Shu
supporting information, p. 5172 - 5176 (2018/09/12)
Heterogeneous nitrogen-doped carbon-incarcerated cobalt/copper bimetallic nanoparticle (NP) catalysts, prepared from nitrogen-containing polymers, were developed, and an efficient catalytic process for aerobic oxidative esterification was achieved in the presence of a low loading (1 mol %) of catalyst that could be reused and easily reactivated. This protocol enabled diverse conditions for the bimetallic NP formation step to be screened, and significant rate acceleration by inclusion of a copper dopant was discovered. The catalytic activity of the bimetallic Co/Cu catalysts is much higher than that for cobalt catalysts reported to date and is even comparable with noble-metal NP catalysts.