Synthesis and biological activities of new conformationally fixed analogues of (-)-indolactam-V, the core structure of tumor-promoting teleocidins

Kazuhiro Irie; Fumito Koizumi; Yoriko Iwata; Takashi Ishii; Yoshiaki Yanai; Yoshimasa Nakamura; Hajime Ohigashi; Paul A. Wender

doi:10.1016/0960-894X(95)00047-W

Synthesis and biological activities of new conformationally fixed analogues of (-)-indolactam-V, the core structure of tumor-promoting teleocidins

Kazuhiro Irie, Fumito Koizumi, Yoriko Iwata, Takashi Ishii, Yoshiaki Yanai, Yoshimasa Nakamura, Hajime Ohigashi, Paul A. Wender

Research output: Contribution to journal › Article

12 Citations (Scopus)

Abstract

(-)-Indolactam-V (1) exists as two stable conformers, the twist and the sofa form, in solution at room temperature. 3-Aza-Cope rearrangement of (-)-N¹³-desmethyl-N¹³-allylindolactam-V (5) gave new conformationally restricted analogues (2a and 3) along with a normal rearrangement product (7). Both 2a and 3, whose fixed conformation was the twist form, showed significant biological activities related to tumor promotion.

Original language	English
Pages (from-to)	453-458
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	5
Issue number	5
DOIs	https://doi.org/10.1016/0960-894X(95)00047-W
Publication status	Published - Mar 2 1995
Externally published	Yes

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ASJC Scopus subject areas

Biochemistry
Clinical Biochemistry
Molecular Biology
Molecular Medicine
Organic Chemistry
Drug Discovery
Pharmaceutical Science

Cite this

Irie, K., Koizumi, F., Iwata, Y., Ishii, T., Yanai, Y., Nakamura, Y., Ohigashi, H., & Wender, P. A. (1995). Synthesis and biological activities of new conformationally fixed analogues of (-)-indolactam-V, the core structure of tumor-promoting teleocidins. Bioorganic and Medicinal Chemistry Letters, 5(5), 453-458. https://doi.org/10.1016/0960-894X(95)00047-W

Synthesis and biological activities of new conformationally fixed analogues of (-)-indolactam-V, the core structure of tumor-promoting teleocidins. / Irie, Kazuhiro; Koizumi, Fumito; Iwata, Yoriko; Ishii, Takashi; Yanai, Yoshiaki; Nakamura, Yoshimasa; Ohigashi, Hajime; Wender, Paul A.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 5, No. 5, 02.03.1995, p. 453-458.

Research output: Contribution to journal › Article

Irie, Kazuhiro ; Koizumi, Fumito ; Iwata, Yoriko ; Ishii, Takashi ; Yanai, Yoshiaki ; Nakamura, Yoshimasa ; Ohigashi, Hajime ; Wender, Paul A. / Synthesis and biological activities of new conformationally fixed analogues of (-)-indolactam-V, the core structure of tumor-promoting teleocidins. In: Bioorganic and Medicinal Chemistry Letters. 1995 ; Vol. 5, No. 5. pp. 453-458.

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