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

Access to Document

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

Fingerprint Dive into the research topics of 'Synthesis and biological activities of new conformationally fixed analogues of (-)-indolactam-V, the core structure of tumor-promoting teleocidins'. Together they form a unique fingerprint.

Cite this

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.

@article{3e8cdf0a827543f88ac423486c4f00f6,

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.}",

year = "1995",

month = mar,

day = "2",

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

language = "English",

volume = "5",

pages = "453--458",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "5",

}

TY - JOUR

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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0028935575&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028935575&partnerID=8YFLogxK

U2 - 10.1016/0960-894X(95)00047-W

DO - 10.1016/0960-894X(95)00047-W

M3 - Article

AN - SCOPUS:0028935575

VL - 5

SP - 453

EP - 458

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 5

ER -