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

ASJC Scopus subject areas

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

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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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