2009
DOI: 10.3998/ark.5550190.0010.605
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Synthesis of tetra- and pentacyclic carbazole-fused imides as potential antitumor agents

Abstract: A series of tetra-and pentacyclic imides with a carbazole skeleton and a basic side chain at the imide nitrogen was synthesized by cyclization of carbazole-2,3-dicarboxylic acid esters with an appropriate amine or via an N-aminoimide as a reactive intermediate. The target compounds 6 and 9 were tested in vitro for tumor cell-growth inhibition

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Cited by 11 publications
(3 citation statements)
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“…4 Moreover, it has been shown that the presence of a basic side chain of the N,N-dialkylaminoalkyl type enhances the drugs' DNA affinity. 5 On the other hand, guanidine-containing heterocycles are known by their anticancer activities. [6][7][8][9][10][11][12] In a preceding Letter of our laboratory, we have described the synthesis of several 2-dialkylamino-5,11-dimethyl-6Hpyrimido [5,4-b]carbazol-4(3H)-ones (VII) 13 as new analogs of ellipticine I, via a simple and efficient one-pot reaction.…”
Section: Introductionmentioning
confidence: 99%
“…4 Moreover, it has been shown that the presence of a basic side chain of the N,N-dialkylaminoalkyl type enhances the drugs' DNA affinity. 5 On the other hand, guanidine-containing heterocycles are known by their anticancer activities. [6][7][8][9][10][11][12] In a preceding Letter of our laboratory, we have described the synthesis of several 2-dialkylamino-5,11-dimethyl-6Hpyrimido [5,4-b]carbazol-4(3H)-ones (VII) 13 as new analogs of ellipticine I, via a simple and efficient one-pot reaction.…”
Section: Introductionmentioning
confidence: 99%
“…The cytotoxic effects are based on the highly active aziridinium cation intermediates arising from the bis(2-chloroethyl)amine moiety [1]. In continuation of our department's previous studies in the field of antitumor agents [2][3][4][5][6][7][8][9], we are reporting in this paper the synthesis of the oxonaphthalene-annelated pyrrole 3 with an attached side chain containing a bis(2-chloroethyl)amine group. The cytotoxic activity of 3 was evaluated.…”
Section: Introductionmentioning
confidence: 99%
“…Among them, pyridazino [4,5-b]carbazoles (representing a 3-aza-olivacine scaffold) have been reported by us [5][6][7][8] and others [9]. As a key intermediate for the synthesis of these tetracycles, 1-methylcarbazole-2,3-dicarboxylic esters have been used and the latter were found to provide a convenient access also to some cytotoxic 4-methylpyrrolo [3,4-b]carbazole-1,3(2H,5H)-diones [10], which again feature the 1-methylcarbazole motif. In the course of extensive structural variation of the A-ring substitution pattern of such b-fused 1-methylcarbazoles, we recently reported the synthesis and cyclisation reactions of some halo-and nitro-substituted 1-methylcarbazole-2,3-dicarboxylic acid dimethyl esters [11].…”
mentioning
confidence: 99%