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 › peer-review

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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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 › peer-review

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

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.",

author = "Kazuhiro Irie and Fumito Koizumi and Yoriko Iwata and Takashi Ishii and Yoshiaki Yanai and Yoshimasa Nakamura and Hajime Ohigashi and Wender, {Paul A.}",

note = "Funding Information: We thank Dr. J. Oda and Ms. K. Omine of the institute for Chemical Research at Kyoto University, Mr. R. Imamura of the Faculty of Science at Kyoto University for the IH NMR measurements. This work was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas No.06240228 and for Encouragement of Young Scientists No.06760109 from the Ministry of Education, Science and Culture, Japan.",

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doi = "10.1016/0960-894X(95)00047-W",

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T1 - Synthesis and biological activities of new conformationally fixed analogues of (-)-indolactam-V, the core structure of tumor-promoting teleocidins

AU - Irie, Kazuhiro

AU - Koizumi, Fumito

AU - Iwata, Yoriko

AU - Ishii, Takashi

AU - Yanai, Yoshiaki

AU - Nakamura, Yoshimasa

AU - Ohigashi, Hajime

AU - Wender, Paul A.

N1 - Funding Information: We thank Dr. J. Oda and Ms. K. Omine of the institute for Chemical Research at Kyoto University, Mr. R. Imamura of the Faculty of Science at Kyoto University for the IH NMR measurements. This work was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas No.06240228 and for Encouragement of Young Scientists No.06760109 from the Ministry of Education, Science and Culture, Japan.

PY - 1995/3/2

Y1 - 1995/3/2

N2 - (-)-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.

AB - (-)-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.

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

Abstract

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