8 テレオシジン類の活性立体構造の決定 : 立体配座固定化合物の合成と生物活性(口頭発表の部)

概要

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Tumor-promoting teleocidins are known to exist in an equilibrium between two conformational states, the twist form and the sofa form, in solution. Benzolactam-Vs (BL-Vs), in which the indole ring of indolactam was replaced by a benzene ring and ring size was prescribed by methylelene, were designed in an attempt to reproduce the active conformation of teleocidins and synthsized. The conformational analysis was carried out by ^1H-NMR. The 8-membered lactam (bezolactam-V8, 4) exists only in twist form in solution. Both the 9-membered lactam (benzolactam-V9, 5) and the 10-membered lactam (benzolactam-V10, 6) exist only in sofa form in solution. It has been reported that the biological activities of IL-V are reinforced by introduction of alkyl chain. Alkylated benzolactams (BL-V8-310 (10), BL-V9-310 (11)) were synthesized for the evaluation of the biological activities. The 8-membered lactam (10) showed stronger biological activities than those of indolactam-V. On the other hand, 9-membered lactam (11) showed above 10^3-times less activities than those of 10. These results clearly indicate that the active conformation for tumor-promoting activities of teleocidins is close to the twist form.
天然有機化合物討論会の論文
1993-09-10