- Design, synthesis, and electrophysiological evaluation of NS6740 derivatives: Exploration of the structure-activity relationship for alpha7 nicotinic acetylcholine receptor silent activation
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The α7 nicotinic acetylcholine receptor (nAChR) silent agonists, able to induce receptor desensitization and promote the α7 metabotropic function, are emerging as new promising therapeutic anti-inflammatory agents. Herein, we report the structure–activity
- Pismataro, Maria Chiara,Horenstein, Nicole A.,Stokes, Clare,Quadri, Marta,De Amici, Marco,Papke, Roger L.,Dallanoce, Clelia
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- Synthesis, characterization, molecular docking and in?vitro antimalarial properties of new carboxamides bearing sulphonamide
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Sulphonamides and carboxamides have shown large number of pharmacological properties against different types of diseases among which is malaria. Twenty four new carboxamide derivatives bearing benzenesulphonamoyl alkanamides were synthesized and investigated for their in silico and in?vitro antimalarial and antioxidant properties. The substituted benzenesulphonyl chlorides (1a-c) were treated with various amino acids (2a-h) to obtain the benzenesulphonamoyl alkanamides (3a-x) which were subsequently treated with benzoyl chloride to obtain the N-benzoylated derivatives (5a-f, i-n and q-v). Further reactions of the N-benzoylated derivatives or proline derivatives with 4-aminoacetophenone (6) using boric acid as a catalyst gave the sulphonamide carboxamide derivatives (7a-x) in excellent yields. The in?vitro antimalarial studies showed that all synthesized compounds had antimalarial property. Compound 7k, 7c, 7l, 7s, and 7j had mean MIC value of 0.02, 0.03, 0.05, 0.06 and 0.08?μM respectively comparable with chloroquine 0.06?μM. Compound 7c was the most potent antioxidant agent with IC50 value of 0.045?mM comparable with 0.34?mM for ascorbic acid. In addition to the successful synthesis of the target molecules using boric acid catalysis, the compounds were found to have antimalarial and antioxidant activities comparable with known antimalarial and antioxidant drugs. The class of compounds reported herein have the potential of reducing oxidative stress arising from malaria parasite and chemotherapeutic agent used in the treatment of malaria.
- Ugwu,Okoro,Ukoha,Okafor,Ibezim,Kumar
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p. 349 - 369
(2017/05/04)
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- Synthesis of novel derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane and their evaluation as potential ligands in asymmetric catalysis
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Thirty-seven (most of them novel) chiral derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (2-36, 38, 39) were prepared from (S)-trans-4-hydroxyproline. A selection of these chiral ligands were examined as potential ligands in the preparation of catalysts for the enantioselective addition of diethylzinc to aldehydes and as chiral Lewis acid activators in the asymmetric Diels-Alder reaction. In the former system, diamine 30 induced up to 92 % enantiomeric excess in the formation of (S)-phenyl ethyl carbinol, whereas in the case of the cycloaddition reaction between cyclopentadiene and 3-acryloyloxazolidin-2-one the catalytic complex formed between dimeric derivative 8 and copper triflate [Cu(OTf)2] afforded the expected product in a 95:5 endo/exo ratio and up to 72 % ee for the major diastereomeric product. Finally, some of the novel chiral diamines prepared in this work were also evaluated as potential organocatalysts in the asymmetric amination of ethyl α-phenyl-α-cyano acetate. Bifunctional derivative 12 provided the animated product in excellent yield and with up to 40 % ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Melgar-Fernandez, Roberto,Gonzalez-Olvera, Rodrigo,Olivares-Romero, J. Luis,Gonzalez-Lopez, Vianney,Romero-Ponce, Leticia,Ramirez-Zarate, Maria Del Refugio,Demare, Patricia,Regla, Ignacio,Juaristi, Eusebio
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p. 655 - 672
(2008/09/17)
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- Formal syntheses of (-)- and (+)-aphanorphine from (2S,4R)-4-hydroxyproline
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We describe the efficient formal syntheses of both natural (-)-aphanorphine and unnatural (+)-aphanorphine from the same commercially available amino acid, (2S,4R)-4-hydroxyproline. The tricyclic framework was constructed by intramolecular Friedel-Crafts
- Ma, Zhiqiang,Hu, Hanwei,Xiong, Wanting,Zhai, Hongbin
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p. 7523 - 7531
(2008/02/08)
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- Trans-4-aminoproline, a phytotoxic metabolite with herbicidal activity produced by Ascochyta caulina
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A phytotoxic metabolite, characterized through NMR techniques and synthetic methods as trans-4-aminoproline, was isolated from the culture filtrates of Ascochyta caulina, a promising mycoherbicide for biological control of Chenopodium album. The metabolite, which shows interesting phytotoxic properties, together with ascaulitoxin (recently characterized as N2-β-D-glucoside of the unusual bis-amino acid 2,4,7-triamino-5- hydroxyoctandioc acid) and another unidentified compound, compose an active fraction of A. caulina culture filtrates with promising herbicidal properties. When assayed on leaves of host and non host dicots, including wild and cultivated plants, the trans-4-aminoproline showed a wide range of toxicity, with leaves of C. album being the most sensitive. Other interesting aspects were its inefficacy on several monocots, both cultivated and wild, and its lack of antifungal, antibiotic and zootoxic activities. This is the first report on trans-4-aminoproline as naturally occurring compound and phytotoxic metabolite produced by A. caulina. (C) 2000 Elsevier Science Ltd.
- Evidente, Antonio,Andolfi, Anna,Vurro, Maurizio,Zonno, Maria Chiara,Motta, Andrea
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p. 231 - 237
(2007/10/03)
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- Synthesis of (2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol from (2S)-3,4-dehydroproline derivatives
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(2R,3R,4S)-2-Hydroxymethylpyrrolidine-3,4-diol (1,4-dideoxy-1,4-imino-D-ribitol) was synthesized in five steps from N-protected (2S)-3,4-dehydroproline methyl esters.The stereoselective reaction of osmium tetraoxide with dehydroproline derivatives gave hi
- Goli, Deepa M.,Cheesman, Bruce V.,Hassan, Mohamed E.,Lodaya, Rita,Slama, James T.
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p. 219 - 242
(2007/10/02)
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- Rhodium complexes of chiral phosphines
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Novel chiral phosphines are disclosed which when complexed with rhodium provide catalyst compositions for asymmetric hydrogenations.
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- A SHORT IMPROVED SYSTHESIS OF N-SUBSTITUTED 5-AZA-2-OXA-3-OXO-BICYCLOHEPTANES
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N-Substituted 5-aza-2-oxa-3-oxo-bicycloheptanes are conformationally rigid models that have been used in several 1H-NMR studies.They have previously been obtained by multistep processes.We have devised a one step synthesis for these compounds.The utility of this new route has been demonstrated for five differently N-substituted substrates.
- Bowers-Nemia, Margaret M.,Joullie, Madeleine M.
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p. 817 - 828
(2007/10/02)
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