Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines

Naoto Kojima; Yuki Suga; Hiromi Hayashi; Takao Yamori; Takehiko Yoshimitsu; Tetsuaki Tanaka

doi:10.1016/j.bmcl.2011.08.011

Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines

Naoto Kojima, Yuki Suga, Hiromi Hayashi, Takao Yamori, Takehiko Yoshimitsu, Tetsuaki Tanaka

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

14 Citations (Scopus)

Abstract

The convergent synthesis of C35-fluorinated analogues of solamin, a mono-THF Annonaceous acetogenin, has been achieved by the Sonogashira coupling of the THF ring fragment and the fluorinated γ-lactone fragment. It was revealed that the number of fluorine atoms on the γ-lactone moiety affects the growth inhibitory activities against human cancer cell lines.

Original language	English
Pages (from-to)	5745-5749
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2011.08.011
Publication status	Published - Oct 1 2011
Externally published	Yes

Keywords

Annonaceous acetogenin
Antitumor agent
Chemical synthesis
Fluorinated analogue
Structure-activity relationship

ASJC Scopus subject areas

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

UN SDGs

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

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10.1016/j.bmcl.2011.08.011

Cite this

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title = "Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines",

abstract = "The convergent synthesis of C35-fluorinated analogues of solamin, a mono-THF Annonaceous acetogenin, has been achieved by the Sonogashira coupling of the THF ring fragment and the fluorinated γ-lactone fragment. It was revealed that the number of fluorine atoms on the γ-lactone moiety affects the growth inhibitory activities against human cancer cell lines.",

keywords = "Annonaceous acetogenin, Antitumor agent, Chemical synthesis, Fluorinated analogue, Structure-activity relationship",

author = "Naoto Kojima and Yuki Suga and Hiromi Hayashi and Takao Yamori and Takehiko Yoshimitsu and Tetsuaki Tanaka",

note = "Funding Information: In vitro antiproliferative activities of C35-fluorinated solamins against human cancer cell lines were examined by the Screening Committee of New Anticancer Agents supported by a Grant-in-Aid for Scientific Research on Priority Area {\textquoteleft}Cancer{\textquoteright} from The Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT). This work was supported by a Grant-in-Aid for Young Scientists (B) [No. 21790113, 23790130], a Grant-in-Aid for Scientific Research (B) [No. 22390021], and a Grant-in-Aid for Scientific Research on Innovative Areas [No. 22136006] from The Ministry of Education, Culture, Sports, Science and Technology, Japan . ",

year = "2011",

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doi = "10.1016/j.bmcl.2011.08.011",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines

AU - Kojima, Naoto

AU - Suga, Yuki

AU - Hayashi, Hiromi

AU - Yamori, Takao

AU - Yoshimitsu, Takehiko

AU - Tanaka, Tetsuaki

N1 - Funding Information: In vitro antiproliferative activities of C35-fluorinated solamins against human cancer cell lines were examined by the Screening Committee of New Anticancer Agents supported by a Grant-in-Aid for Scientific Research on Priority Area ‘Cancer’ from The Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT). This work was supported by a Grant-in-Aid for Young Scientists (B) [No. 21790113, 23790130], a Grant-in-Aid for Scientific Research (B) [No. 22390021], and a Grant-in-Aid for Scientific Research on Innovative Areas [No. 22136006] from The Ministry of Education, Culture, Sports, Science and Technology, Japan .

PY - 2011/10/1

Y1 - 2011/10/1

N2 - The convergent synthesis of C35-fluorinated analogues of solamin, a mono-THF Annonaceous acetogenin, has been achieved by the Sonogashira coupling of the THF ring fragment and the fluorinated γ-lactone fragment. It was revealed that the number of fluorine atoms on the γ-lactone moiety affects the growth inhibitory activities against human cancer cell lines.

AB - The convergent synthesis of C35-fluorinated analogues of solamin, a mono-THF Annonaceous acetogenin, has been achieved by the Sonogashira coupling of the THF ring fragment and the fluorinated γ-lactone fragment. It was revealed that the number of fluorine atoms on the γ-lactone moiety affects the growth inhibitory activities against human cancer cell lines.

KW - Annonaceous acetogenin

KW - Antitumor agent

KW - Chemical synthesis

KW - Fluorinated analogue

KW - Structure-activity relationship

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JO - Bioorganic and Medicinal Chemistry Letters

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SN - 0960-894X

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ER -

Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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