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Analogues et dérivés inédits des benzo[c]phénanthridines antitumorales. Synthèse et étude biologique

Abstract : The work presented deals with the preparation of some analogs of the antitumor benzo[c]phenanthridine alcaloids such as nitidine and fagaronine and bearing a dimethylaminoalkylamino side-chain on the carbon 6 of this tetracyclic ring system. The detailed synthetic work described in this report includes:
- The discovery of a new synthetic means to prepare alkoxylated-1-aminonaphtalenes from their corresponding 1-tetralones. From these amines, the generalization of a synthetic path to the 7,8,9,10-tetrahydrobenzo[c]phenanthridin-6(5H)-ones enabled us to prepare 16 benzo[c]phenanthridine derivatives mono or bis functionnalized.
- A study of Robinson's access to the benzo[c]phenanthridine was performed in order to prepare tetraoxygenated analogs. In the course of this study, we found conditions to prepare the previously unreported 2-aryl-1-naphthylamines from 2-aryl-1-tetraloneoximes using the Semmler-Wolff reaction. From these amines through the corresponding urethane, thermal cyclization gave benzo[c]phenanthridin-6(5H)-ones, readily transformed into the 6-chlorinated derivatives. Not only substitution gave the tetraoxygenated analogs, but this synthesis is actually a new access to this type of alcaloïd.
- Also, the condensation between 6-methoxy-1-tetralone, methylpropiolate and ammonia which yielded 8-methoxy-5,6-dihydrobenzo[h]quinolin-2(1H)-one enabled us to prepare four benzo[h]quinoline derivatives substituted with the above-mentionned amino side chain on carbon 2.
The results of cytotoxicity tests of all the compounds and antitumoral activity of some are given.
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Contributor : Yves Janin Connect in order to contact the contributor
Submitted on : Thursday, September 27, 2007 - 10:06:57 AM
Last modification on : Tuesday, November 16, 2021 - 4:36:19 AM
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  • HAL Id : tel-00175198, version 1


Yves Louis Janin. Analogues et dérivés inédits des benzo[c]phénanthridines antitumorales. Synthèse et étude biologique. Autre. Université Pierre et Marie Curie - Paris VI, 1993. Français. ⟨tel-00175198⟩



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