Tetrahedron p. 4258 - 4272 (2016)
Update date:2022-08-10
Topics:
Kato, Asako
Nagatsuka, Yusuke
Hiratsuka, Tomokazu
Kiuchi, Satoko
Iwase, Yoko
Okuno, Yuri
Tsukamoto, Tetsuya
Kiran
Sakai, Norio
Konakahara, Takeo
Thirty-five types of novel pyridocarbazoles (5-(N-alkyl)carbamoyl-11-methyl-6H-pyrido[4,3-b]carbazoles and 5-(N-alkyl)carbamoyl-2,11-dimethyl-6H-pyrido[4,3-b]carbazol-2-ium chloride derivatives), that were conjugated with amine, N-methylurea, and N-methyl-N-nitrosourea moieties through alkyl-, oxyalkyl-, and iminoalkylcarbamoyl linkers, were synthesized by a series of reactions of methyl 11-methyl-6H-pyrido[4,3-b]carbazole-5-carboxylates with polymethylenediamine (n=2–5), p-nitrophenyl N-methylcarbamate, and N-methyl-N-nitrosocarbamate in high yields, and their cytotoxic activities were evaluated against Sarcoma-180, NIH3T3, HeLa S-3, and L1210?cell lines. These compounds exhibited potent cytotoxic activity (IC50=1.6–50?μM) and odd-even alternation effect. 9-Methoxy-2,11-dimethyl-5-((2-(3-methyl-3-nitrosoureido)ethyl)carbamoyl)-6H-pyrido[4,3-b]carbazol-2-ium chloride exhibited the most potent cytotoxic activity (IC50=0.15?μM) and cell selectivity against HeLa S-3. Some of the un-charged 5-(N-alkyl)carbamoyl-6H-pyrido[4,3-b]carbazole derivatives, which were conjugated with the amine and N-methyl-N-nitrosourea moieties through a dimethylene spacer, also exhibited potent cytotoxic activity (IC50=0.43–2.4?μM) and remarkable cell selectivity as well as ellipticine, 9-hydroxyellipticine, and the starting methyl ester of the pyridocarbazole-5-carboxylate (IC50=0.30–2.2?μM).
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Doi:10.1246/bcsj.58.2600
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