83 Teleocidin誘導体の合成,立体配座解析および生物活性

概要

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Teleocidin B (1) and teleocidin A(2) have been proved to be very potent skin tumor promoters. The common structural fragment includes an indole and a nine-membered lactam, which seem to be indispensable to the biological activities. We synthesized the structure, i.e. (-)-indolactam-V((-)-3) and its stereoisomers ((+)-3,(+)-16,(-)-16). (-)-3, but not the antipode or epimers, was found to exhibit several of the essential biological effects of tumor promoters. These teleocidin derivatives (1, 2, (-)-3 and so on) were found to exist in two stable conformational states in solution on the basis of ^1H-NMR study (Figure 1). The structure of the two conformations were deduced from the NMR spectra of 3 and 4, and were refined by empirical force field calculation using Allinger's MM2 program. The structures for 3 illustrated in Figure 2. The conversion of conformer A to B could be accomplished mainly by the rotation of the amide C-N bond from trans to cis. We also synthesized indolactam derivatives (21-26, 29-32) and investigated their biological activities.
天然有機化合物討論会の論文
1985-09-07