522-66-7Relevant articles and documents
Convenient synthesis of cobalt nanoparticles for the hydrogenation of quinolines in water
Beller, Matthias,Dorcet, Vincent,Fischmeister, Cedric,Hervochon, Julien,Junge, Kathrin
, p. 4820 - 4826 (2020/08/14)
Easily accessible cobalt nanoparticles are prepared by hydrolysis of NaBH4 in the presence of inexpensive Co(ii) salts. The resulting material is an efficient catalyst for the hydrogenation of quinoline derivatives in water. The activity and chemoselectivity of this catalyst are comparable to other cobalt-based heterogeneous catalysts.
A Cinchona Alkaloid Antibiotic That Appears to Target ATP Synthase in Streptococcus pneumoniae
Wang, Xu,Zeng, Yuna,Sheng, Li,Larson, Peter,Liu, Xue,Zou, Xiaowen,Wang, Shufang,Guo, Kaijing,Ma, Chen,Zhang, Gang,Cui, Huaqing,Ferguson, David M.,Li, Yan,Zhang, Jingren,Aldrich, Courtney C.
, p. 2305 - 2332 (2019/04/25)
Optochin, a cinchona alkaloid derivative discovered over 100 years ago, possesses highly selective antibacterial activity toward Streptococcus pneumoniae. Pneumococcal disease remains the leading source of bacterial pneumonia and meningitis worldwide. The structure-activity relationships of optochin were examined through modification to both the quinoline and quinuclidine subunits, which led to the identification of analogue 48 with substantially improved activity. Resistance and molecular modeling studies indicate that 48 likely binds to the c-ring of ATP synthase near the conserved glutamate 52 ion-binding site, while mechanistic studies demonstrated that 48 causes cytoplasmic acidification. Initial pharmacokinetic and drug metabolism analyses of optochin and 48 revealed limitations of these quinine analogues, which were rapidly cleared, resulting in poor in vivo exposure through hydroxylation pendants to the quinuclidine and O-dealkylation of the quinoline. Collectively, the results provide a foundation to advance 48 and highlight ATP synthase as a promising target for antibiotic development.
Expansion of the aromatic part of Cinchona alkaloids. Annulation of quinolines with phenoxazine motifs
W?sińska-Ka?wa, Ma?gorzata,Giurg, Miros?aw,Boratyński, Przemys?aw J.,Skar?ewski, Jacek
, p. 308 - 315 (2017/12/08)
An oxidative cross-coupling strategy for quinoline ring annulation in Cinchona alkaloids has been developed. Key-reaction optimization by changing oxidants and adjusting the nucleophilicity of the 2-aminophenols led to cupreine and cupreidine expanded with the phenoxazinone unit in 56–75% yield. The stereochemical integrity of the obtained alkaloid structures was confirmed by combined experimental and computed CD and NMR data. The conformational study revealed a fast equilibrium of the three conformers, differing in the orientation of the pyrido[a-3,2]phenoxazine moiety.
