- Synthesis and antimicrobial activities of monoindolyl- and bisindolyloximes
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Six monoindolyl- and bisindolyloximes structurally related to protein kinase C inhibitors bisindolylmaleimides were synthezised. They did not have protein kinase C inhibitory properties but exhibited interesting antimicrobial activities. Their antibacterial activities against several strains of pathogenic and non-pathogenic Gram-positive and Gram-negative bacteria are described. The bisindolyl monooxime isomers exhibited a marked activity against the three strains of Staphylococcus aureus tested and against Escherichia coli 1507E.
- Prudhomme, Michelle,Sancelme, Martine,Bonnefoy, Alain,Fabbro, Doriano,Meyer, Thomas
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- Hexahydropyrroloindoles - Attempts to Synthesize 2-Indolyl Thioethers
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The N-tryptamine derivatives 9, 11, 12, and 19 with the functional groups CN, CONH2, CO2H, and CO2Me, respectively, in the α position to the indole ring have been synthesized.Sensitized photooxiation of 9, 12, 19, N-Boc--tryptophan (21), and N-Boc-tryptamine (22) affords the hexahydropyrroloindoles 23-27, in the case of 11 the ring closure occurs at the amine nitrogen to give the ketone 28, N-Boc-homotryptamine (31) yields the hexahydropyridoindole 32, whereas no azetidine formation from 2-(3-indolyl)glycine (36) is observed.The oxi mes 34a and 34 b, intermediates in the synthesis of 36, have been separated chromatographically and characterized NMR spectroscopically as E and Z-isomers, respectively.- Attempts to introduce with cysteine derivatives a thioether group in position 2 of the compounds described above, failed. 21, 22, 26, 27, and N-Boc-2-(3-indolyl)propylamine (43), bearing a methyl group in the α position to the indole ring, and its photooxidation product 44 show only thin-layer chromatographically detectable thioether formation.
- Droste, Holger,Wieland, Theodor
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p. 901 - 910
(2007/10/02)
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