| Autor: |
Biot C; Laboratoire de catalyse de Lille, groupe de synthèse organométallique, UPRESA 8010, école nationale supérieure de chimie de Lille, bâtiment C7 université des sciences et technologies BP 108, Villeneuve, France., Delhaes L, Maciejewski LA, Mortuaire M, Camus D, Dive D, Brocard JS |
| Jazyk: |
angličtina |
| Zdroj: |
European journal of medicinal chemistry [Eur J Med Chem] 2000 Jul-Aug; Vol. 35 (7-8), pp. 707-14. |
| DOI: |
10.1016/s0223-5234(00)00178-1 |
| Abstrakt: |
A few years ago we proposed a strategy for the synthesis of new ferrocene-chloroquine analogues replacing the carbon chain of chloroquine by hydrophobic ferrocenyl moieties. Now, this strategy has been applied to the antimalarial amino-alcohols class to afford new potentially active analogues of mefloquine and quinine bearing a substituted ferrocenic group. The pathway used for the synthesis of the mefloquine analogues includes the coupling of an aminomethyl substituted ferrocene carboxaldehyde with a lithio quinoline compound. On the other hand, the synthesis of quinine analogues was ensured by the 'inverse' reaction of a lithio aminomethyl ferrocene with a quinoline carboxaldehyde. The configurations of each diastereoisomer were unambiguously determined by spectroscopic data. The mechanistic interpretations were fully discussed. Ferrocenyl analogues of mefloquine and quinine exhibited a lower antimalarial activity than mefloquine and quinine themselves. Comparing optical isomers, those isomers dissimilar to ferrocenyl derivatives presented better antimalarial activities than those similar to ferrocenyl. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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