46708-03-6Relevant articles and documents
Inhibition of Yeast-to-Hypha Transition and Virulence of Candida albicans by 2-Alkylaminoquinoline Derivatives
Meng, Lili,Zhao, He,Zhao, Shuo,Sun, Xiuyun,Zhang, Min,Deng, Yinyue
, (2019)
A rapid increase in Candida albicans infection and drug resistance has caused an emergent need for new clinical strategies against this fungal pathogen. In this study, we evaluated the inhibitory activity of a series of 2-alkylaminoquinoline derivatives against C. albicans isolates. A total of 28 compounds were assessed for their efficacy in inhibiting the yeast-to-hypha transition, which is considered one of the key virulence factors in C. albicans. Several compounds showed strong activity to decrease the morphological transition and virulence of C. albicans cells. The two leading compounds, compound 1 (2-[piperidin-1-yl]quinolone) and compound 12 (6-methyl-2-[piperidin-1-yl]quinoline), remarkably attenuated C. albicans hyphal formation and cytotoxicity in a dose-dependent manner, but they showed no toxicity to either C. albicans cells or human cells. Intriguingly, compound 12 showed an excellent ability to inhibit C. albicans infection in the mouse oral mucosal infection model. This leading compound also interfered with the expression levels of hypha-specific genes in the cyclic AMP-protein kinase A and mitogen-activated protein kinase signaling pathways. Our findings suggest that 2-alkylaminoquinoline derivatives could potentially be developed as novel therapeutic agents against C. albicans infection due to their interference with the yeast-to-hypha transition.
Copper/manganese oxide catalyzed regioselective amination of quinoline N-oxides: An example of synergistic cooperative catalysis
Sahoo, Tapan,Thakur, Dinesh,Panda, Asit Baran,Ghosh, Subhash Chandra
, (2021/09/29)
An atom economical and efficient protocol for C-2 amination of quinoline N-oxides using our synthesized recyclable heterogeneous Cu–MnO catalyst has been reported here. Direct C[sbnd]H aminations of heterocyclic N-oxides with secondary amine were carried out under base, and ligand-free conditions in good to excellent yields. The major advantage is that air is used as a sole oxidant and our catalyst is recycled several times.
A mild and metal-free synthesis of 2- And 1-alkyl/aryl/dialkyl-aminoquinolines and isoquinolines
Nanaji, Yerramsetti,Kirar, Seema,Pawar, Sandip V.,Yadav, Ashok Kumar
, p. 7628 - 7634 (2020/03/13)
A simple synthetic strategy has been developed for the synthesis of 2- and 1-alkyl/aryl/dialkylaminoquinolines and isoquinolines from the easily available quinoline and isoquinoline-N-oxides, different amines, triflic anhydride as activating agent and ace
Nucleophilic amination of methoxypyridines by a sodium hydride-iodide composite
Pang, Jia Hao,Kaga, Atsushi,Chiba, Shunsuke
supporting information, p. 10324 - 10327 (2018/09/21)
A new protocol for nucleophilic amination of methoxypyridines and their derivatives was developed using sodium hydride (NaH) in the presence of lithium iodide (LiI). The method offers a concise access to various aminopyridines which are potentially of medicinal interest.
2-alkylamine quinoline compound for preventing and treating candida albicans as well as preparation method and application of 2-alkylamine quinoline compound
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Paragraph 0017; 0028; 0029; 0030; 0031, (2018/08/04)
The invention belongs to the technical field of biomedicines and in particular relates to a 2-alkylamine quinoline compound for preventing and treating candida albicans as well as a preparation methodand application of the 2-alkylamine quinoline compound. The compound is prepared from a compound A (1,2,3,4-Tetrahydroquinolines) and a compound B (O-benzoyl hydroxylamines) as raw materials throughsynthesis. Compared with the prior art, the compound has the advantages and effects that results of former research of the inventor show that a diffusible signal factor (DSF) quorum sensing signal anda derivative thereof are capable of relatively intensely interfering conversion of a yeast state to a hypha state of candida albicans, and the compound capable of inhibiting adhesion, hypha state conversion and pathogenicity of the candida albicans is successfully synthesized and screened in the research. Meanwhile, the compound is relatively small in toxicity, growth of the candida albicans andhuman cells is not affected, and the characteristics have the potential of promoting development of novel antifungal drugs.
Copper-Catalyzed Cross-Dehydrogenative Coupling of N-Iminoquinolinium Ylides with Secondary Amines
Hua, Zerui,Fang, Lei,Wu, Shengying,Wang, Limin
, p. 4953 - 4956 (2016/10/26)
The copper-catalyzed cross-dehydrogenative coupling of N-iminoquinolinium ylides with secondary amines led to ortho-amino-substituted quinoline derivatives with high levels of regioselectivity in good yields. This direct C–H bond amination transformation employs CuI as the catalyst without the use of a ligand, external oxidant, or base. The reaction is operationally simple and can be conducted under mild conditions. The N-benzoyl directing group can be removed without any additional steps.
Copper-catalyzed direct amination of quinoline N-oxides via C-H bond activation under mild conditions
Zhu, Chongwei,Yi, Meiling,Wei, Donghui,Chen, Xuan,Wu, Yangjie,Cui, Xiuling
, p. 1840 - 1843 (2014/05/06)
A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C-N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions.
Room-temperature nickel-catalyzed amination of heteroaryl/aryl chlorides with Ni(II)-(σ-Aryl) complex as precatalyst
Fan, Xin-Heng,Li, Gang,Yang, Lian-Ming
experimental part, p. 2482 - 2484 (2011/07/07)
The room-temperature cross-coupling of heteroaryl and aryl chlorides with secondary cyclic amines can be effected using Ni(II)-(σ-aryl) complex as pre-catalyst. Some useful aromatic and heteroaromatic amine derivatives were readily synthesized in moderate to good yields in the presence of the Ni(II)-(σ-aryl) complex/NHC/KOtBu/toluene system.
Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists
Saari, Raimo,T?rm?, Jonna-Carita,Nevalainen, Tapio
experimental part, p. 939 - 950 (2011/03/19)
Quinoline, isoquinoline, quinoxaline, and quinazoline derivatives were synthesized using microwave-assisted synthesis and their CB1/CB2 receptor activities were determined using the [35S]GTPγS binding assay. Most of the prepared quinoline, isoquinoline, and quinoxalinyl phenyl amines showed low-potency partial CB2 receptor agonists activity. The most potent CB2 ligand was the 4-morpholinylmethanone derivative (compound 40e) (-log EC 50 = 7.8; Emax = 75%). The isoquinolin-1-yl(3- trifluoromethyl-phenyl)amine (compound 26c) was a high efficacy CB2 agonist (-log EC50 = 5.8; Emax = 128%). No significant CB1 receptor activation or inactivation was shown in these studies, except 40e, which showed weak CB1 agonist activity (CB1 -log EC50 = 5.0). These ligands serve as novel templates for the development of selective CB2 receptor agonist.
Cobalt-catalyzed C-N bond-forming reaction between N-aromatic 2-chlorides and secondary amines
Toma, Gabriel,Fujita, Ken-Ichi,Yamaguchi, Ryohei
scheme or table, p. 4586 - 4588 (2009/12/05)
Secondary amines react with N-aromatic 2-chlorides in the presence of a catalytic amount of cobalt chloride. When DPPP was added as ligand, the yield was further improved, The N-aromatic-containing tertiary amines formed are interesting due to their poten
