- In vitro antiplasmodial activity of triazole-linked chloroquinoline derivatives synthesized from 7-chloro-N-(prop-2-yn-1-yl)quinolin-4-amine
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The synthesis and in vitro evaluation of novel triazole-linked chloroquinoline derivatives as potential antiplasmodial agents against Plasmodium falciparum is reported. The 15 synthesized target compounds were obtained by means of a copper(I)-mediated click reaction between a variety of 1,2- and 1,3-azidoamines and 7-chloro-N-(prop-2-yn-1-yl)quinolin-4-amine in moderate to good yields (53-85%). The compounds were screened for antiplasmodial activity against NF54 chloroquine-sensitive and Dd2 chloroquine-resistant strains, alongside chloroquine and artesunate as reference compounds. Six of the test compounds revealed a 3-5 fold increase in antiplasmodial activity against chloroquine-resistant strain Dd2 compared to chloroquine. Among the six compounds with good antiplasmodial activity, a reduced cross-resistance relative to artesunate (>3 fold in comparison to chloroquine) was observed, mainly in derivatives that incorporated chloroquine-resistance reversing pharmacophores. A general trend for reduced chloroquine cross-resistance was also detected among 12 out of the 15 compounds tested.
- Taleli, Lebusetsa,De Kock, Carmen,Smith, Peter J.,Pelly, Stephen C.,Blackie, Margaret A.L.,Van Otterlo, Willem A.L.
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p. A4163 - A4171
(2015/08/03)
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- Facile calculation of specific rate constants and activation energies of 18F-fluorination reaction using combined processes of coat-capture-elution and microfluidics
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Calculation of a specific rate constant (k) and activation energy (E a) of 18F-labeling reaction is important to obtain objective data. However, it has never been tried, because short time heating required for the calculation of the
- Yang, Bo Yeun,Jeong, Jae Min,Lee, Yun-Sang,Lee, Dong Soo,Chung, June-Key,Lee, Myung Chul
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supporting information; experimental part
p. 2427 - 2433
(2011/05/02)
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- Synthesis of C3- and C2-symmetric tris- and bis-sulfoxide ligands by asymmetric oxidation
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A series of tris- and bis-sulfoxides were synthesized by multiple asymmetric oxidation of the corresponding sulfides. High enantioselectivities were obtained based on Horeau-type amplification of selectivity. Naphthyl-substituted sulfoxides allowed for higher selectivity and greater ease of purification. These sulfoxides were tested as ligands in rhodium-catalyzed olefin hydroacylation and 1,4-addition of phenyl boronic acid to 2-cyclohexen-1-one. While no enantioinduction was observed in hydroacylation, up to 80% ee was obtained for a tris-sulfoxide and a bis-sulfoxide ligand in the 1,4-addition. Bis-sulfoxides with flexible backbones gave lower and inversed enantioselectivity, suggesting backbone rigidity plays a key role in enantioinduction.
- Dornan, Peter K.,Leung, Priscilla L.,Dong, Vy M.
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experimental part
p. 4378 - 4384
(2011/08/04)
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- Polybenzocrown ethers: Synthesis by cesium-assisted cyclization and solid-state structures
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A series of large-ring polybenzocrown ethers is prepared by cesium-assisted cyclizations. Reactions of diphenols/bisphenols, dimesylates of oligoethylene glycols and cesium carbonate in MeCN produce the large-ring polybenzocrown ethers in high yields. To gain further insight into the structures of these compounds, solid-state structures of three large-ring crown ethers are obtained by X-ray diffraction.
- Hanes, Robert E.,Ellingsworth, Edward C.,Griffin, Scott T.,Rogers, Robin D.,Bartsch, Richard A.
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p. 217 - 237,21
(2020/08/24)
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- Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones
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Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.
- Poldy, Jacqueline,Peakall, Rod,Barrow, Russell A.
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p. 2446 - 2449
(2008/09/20)
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- Rationally-designed S-chiral bissulfinamides as highly enantioselective organocatalysts for reduction of ketimines
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We recently reported the first example of S-chiral organocatalysts, that are highly efficient and enantioselective in substoichometric amounts, and which use a chiral monosulfinamide group as Lewis base to activate trichlorosilane (HSiCl3) to reduce N-arylketimines. Aplausible mechanism involving two molecules of the monosulfinamde catalyst for the activation of HSiCl 3 prompted us to design S-chiral bissulfinamides as new catalysts. We herein describe our findings that an easily prepared S-chiral bissulfinamide bearing a five-methylene linkage not only inherited the excellent substrate generality from the monosulfinamide catalysts, but also exhibited further improved enantioselectivity.
- Pei, Dong,Zhang, Yu,Wei, Siyu,Wang, Meng,Sun, Jian
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supporting information; experimental part
p. 619 - 623
(2009/04/21)
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- Synthesis and biological evaluation of a series of novel N- or O-fluoroalkyl derivatives of tropane: Potential positron emission tomography (PET) imaging agents for the dopamine transporter
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A series of novel fluoroalkyl-containing tropane derivatives was synthesized, and their binding affinities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) were determined via competitive binding assays. Among these derivatives, the fluoropropyl ester of β-CIT (19), the fluoroethyl ester of β-CIT (20), the N-fluoropropyl derivative of β-CBT (12), and the fluoropropyl ester of β-CMT (18) displayed higher affinity and greater selectivity for the DAT versus SERT and NET than FP-CIT, which indicates that they are attractive candidates for the development of 18F-labeled PET imaging agents for the DAT.
- Gu, Xiao-Hui,Zong, Rushi,Kula, Nora S.,Baldessarini, Ross J.,Neumeyer, John L.
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p. 3049 - 3053
(2007/10/03)
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