- Synthesis and structure-activity relationship of Huprine derivatives as human acetylcholinesterase inhibitors
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New series of Huprine (12-amino-6,7,10,11-tetrahydro-7,11-methanocycloocta[b]quinolines) derivatives have been synthesized and their inhibiting activities toward recombinant human acetylcholinesterase (rh-AChE) are reported. We have synthesized two series of Huprine analogues; in the first one, the benzene ring of the quinoline moiety has been replaced by different heterocycles or electron-withdrawing or electron-donating substituted phenyl group. The second one has been designed in order to evaluate the influence of modification at position 12 where different short linkers have been introduced on the Huprine X, Y skeletons. All these molecules have been prepared from ethyl- or methyl-bicyclo[3.3.1]non-6-en-3-one via Friedlaender reaction involving selected o-aminocyano aromatic compounds. The synthesis of two heterodimers based on these Huprines has been also reported. Activities from moderate to same range than the most active Huprines X and Y taken as references have been obtained, the most potent analogue being about three times less active than parent Huprines X and Y. Topologic data have been inferred from molecular dockings and variations of activity between the different linkers suggest future structural modifications for activity improvement.
- Ronco, Cyril,Sorin, Geoffroy,Nachon, Florian,Foucault, Richard,Jean, Ludovic,Romieu, Anthony,Renard, Pierre-Yves
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supporting information; experimental part
p. 4523 - 4536
(2009/12/04)
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- Alkylamino derivatives of 4-aminomethylpyridine as inhibitors of copper-containing amine oxidases
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The first substratelike, reversible inhibitors of different copper amine oxidases (CAOs) with IC50 (M) as low as 2.0 × 10-8 corresponding to derivatives of 4-aminomethylpyridine with alkoxy (1a-d), alkylthio (2a,b), and alkylamino (3
- Bertini, Vincenzo,Buffoni, Franca,Ignesti, Giovanni,Picci, Nevio,Trombino, Sonia,Iemma, Francesca,Alfei, Silvana,Pocci, Marco,Lucchesini, Francesco,De Munno, Angela
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p. 664 - 670
(2007/10/03)
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- Preparation of 4-substituted 3-amino-2-chloropyridines, synthesis of a nevirapine analogue
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A new method for preparing 3-amino-2-chloropyridines with a substituent (methyl, phenyl, carboxamide, methoxycarbonyl, acetyl, benzoyl and cyano) at the 4-position has been developed. An isoquinoline analogue of the reverse transcriptase inhibitor Nevirapine has been synthesized from the 4-amino-3-chloroisoquinoline.
- Bakke,Riha
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- Chemoselective Reactions of 3-Chloroisonicotinonitrile
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Chemoselective reactions of 3-chloroisonicotinonitrile (1) with nucleophiles are described.Treatment of 1 with sodium methoxide/methanol results in formation of the imino ether, which can be further elaborated into a triazole ring.However, when 1 is react
- LaMattina, John L.,Taylor, Richard L.
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p. 4179 - 4182
(2007/10/02)
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