Total Synthesis of Fontanesine B and Its Isomer: Their Antiproliferative Activity against Human Colorectal Cancer Cells

Takumi Abe; Tomoki Itoh; Masaru Terasaki

doi:10.1002/hlca.201900116

Total Synthesis of Fontanesine B and Its Isomer: Their Antiproliferative Activity against Human Colorectal Cancer Cells

Takumi Abe, Tomoki Itoh, Masaru Terasaki

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

A concise synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a Fischer indolization is described. This key Fischer indolization starts with the pyran-ring and alkene intact, facilitating potential synthetic applications. Furthermore, fontanesine B and its isomer were evaluated for in vitro antiproliferative activity against human colorectal cancer cells. The isomer of fontanesine B showed higher antiproliferative activity than the natural product, fontanesine B (2).

Original language	English
Article number	e1900116
Journal	Helvetica Chimica Acta
Volume	102
Issue number	7
DOIs	https://doi.org/10.1002/hlca.201900116
Publication status	Published - Jul 2019
Externally published	Yes

Keywords

alkaloids
antiproliferation
Fischer
indoles
synthetic methods

ASJC Scopus subject areas

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/hlca.201900116

Cite this

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abstract = "A concise synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a Fischer indolization is described. This key Fischer indolization starts with the pyran-ring and alkene intact, facilitating potential synthetic applications. Furthermore, fontanesine B and its isomer were evaluated for in vitro antiproliferative activity against human colorectal cancer cells. The isomer of fontanesine B showed higher antiproliferative activity than the natural product, fontanesine B (2).",

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author = "Takumi Abe and Tomoki Itoh and Masaru Terasaki",

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month = jul,

doi = "10.1002/hlca.201900116",

language = "English",

volume = "102",

journal = "Helvetica Chimica Acta",

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T1 - Total Synthesis of Fontanesine B and Its Isomer

T2 - Their Antiproliferative Activity against Human Colorectal Cancer Cells

AU - Abe, Takumi

AU - Itoh, Tomoki

AU - Terasaki, Masaru

N1 - Funding Information: This work was financially supported by JSPS KAKENHI grant (No. 16 K18849 for T. A., and No. 16 K07880 for M. T.). Publisher Copyright: © 2019 Wiley-VHCA AG, Zurich, Switzerland

PY - 2019/7

Y1 - 2019/7

N2 - A concise synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a Fischer indolization is described. This key Fischer indolization starts with the pyran-ring and alkene intact, facilitating potential synthetic applications. Furthermore, fontanesine B and its isomer were evaluated for in vitro antiproliferative activity against human colorectal cancer cells. The isomer of fontanesine B showed higher antiproliferative activity than the natural product, fontanesine B (2).

AB - A concise synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a Fischer indolization is described. This key Fischer indolization starts with the pyran-ring and alkene intact, facilitating potential synthetic applications. Furthermore, fontanesine B and its isomer were evaluated for in vitro antiproliferative activity against human colorectal cancer cells. The isomer of fontanesine B showed higher antiproliferative activity than the natural product, fontanesine B (2).

KW - alkaloids

KW - antiproliferation

KW - Fischer

KW - indoles

KW - synthetic methods

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M3 - Article

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JF - Helvetica Chimica Acta

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ER -

Total Synthesis of Fontanesine B and Its Isomer: Their Antiproliferative Activity against Human Colorectal Cancer Cells

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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