Catalytic Enantioselective Synthesis of a Pyrrolizidine-Alkaloid-Inspired Compound Collection with Antiplasmodial Activity

Zhi Jun Jia; Hiroshi Takayama; Yushi Futamura; Harumi Aono; Jonathan O. Bauer; Carsten Strohmann; Andrey P. Antonchick; Hiroyuki Osada; Herbert Waldmann

doi:10.1021/acs.joc.7b03202

Catalytic Enantioselective Synthesis of a Pyrrolizidine-Alkaloid-Inspired Compound Collection with Antiplasmodial Activity

Zhi Jun Jia, Hiroshi Takayama, Yushi Futamura, Harumi Aono, Jonathan O. Bauer, Carsten Strohmann, Andrey P. Antonchick^*, Hiroyuki Osada, Herbert Waldmann

^*この研究の対応する著者

研究成果: Article › 査読

10 被引用数 (Scopus)

抄録

A novel enantioselective approach to the synthesis of a compound collection inspired by natural pyrrolizidine alkaloids was developed, employing an enantioselectively catalyzed 1,3-dipolar cycloaddition as the key step. The cycloadducts were obtained with excellent enantio- and diastereoselectivity. Biological evaluation of the resulting compound collection revealed that the compound class has multiple bioactivities, including activity against Plasmodium falciparum 3D7 and inhibition of Hedgehog signaling.

本文言語	English
ページ（範囲）	7033-7041
ページ数	9
ジャーナル	Journal of Organic Chemistry
巻	83
号	13
DOI	https://doi.org/10.1021/acs.joc.7b03202
出版ステータス	Published - 2018 7月 6
外部発表	はい

ASJC Scopus subject areas

有機化学

文献へのアクセス

10.1021/acs.joc.7b03202

他のファイルとリンク

引用スタイル

@article{d624bc96aa7e444b91213d62ed79c8d6,

title = "Catalytic Enantioselective Synthesis of a Pyrrolizidine-Alkaloid-Inspired Compound Collection with Antiplasmodial Activity",

abstract = "A novel enantioselective approach to the synthesis of a compound collection inspired by natural pyrrolizidine alkaloids was developed, employing an enantioselectively catalyzed 1,3-dipolar cycloaddition as the key step. The cycloadducts were obtained with excellent enantio- and diastereoselectivity. Biological evaluation of the resulting compound collection revealed that the compound class has multiple bioactivities, including activity against Plasmodium falciparum 3D7 and inhibition of Hedgehog signaling.",

author = "Jia, {Zhi Jun} and Hiroshi Takayama and Yushi Futamura and Harumi Aono and Bauer, {Jonathan O.} and Carsten Strohmann and Antonchick, {Andrey P.} and Hiroyuki Osada and Herbert Waldmann",

note = "Funding Information: Z.-J.J. thanks the International Max-Planck-Research School in Chemical and Molecular Biology for a fellowship. This research was supported by the European Research Council under the Seventh Framework Programme of the European Union (FP7/2007-2013; ERC Grant 268309 to H.W.) and by the Max Planck Society. We thank Dr. Sonja Sievers and the compound management and screening center (COMAS) for compound screening. We thank Dr. Fuyu Ito, Ms. Naoko Morita, and Ms. Yasuko\ Hirata (RIKEN) for performing the antiproliferative activity tests. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = jul,

day = "6",

doi = "10.1021/acs.joc.7b03202",

language = "English",

volume = "83",

pages = "7033--7041",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Catalytic Enantioselective Synthesis of a Pyrrolizidine-Alkaloid-Inspired Compound Collection with Antiplasmodial Activity

AU - Jia, Zhi Jun

AU - Takayama, Hiroshi

AU - Futamura, Yushi

AU - Aono, Harumi

AU - Bauer, Jonathan O.

AU - Strohmann, Carsten

AU - Antonchick, Andrey P.

AU - Osada, Hiroyuki

AU - Waldmann, Herbert

N1 - Funding Information: Z.-J.J. thanks the International Max-Planck-Research School in Chemical and Molecular Biology for a fellowship. This research was supported by the European Research Council under the Seventh Framework Programme of the European Union (FP7/2007-2013; ERC Grant 268309 to H.W.) and by the Max Planck Society. We thank Dr. Sonja Sievers and the compound management and screening center (COMAS) for compound screening. We thank Dr. Fuyu Ito, Ms. Naoko Morita, and Ms. Yasuko\ Hirata (RIKEN) for performing the antiproliferative activity tests. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/7/6

Y1 - 2018/7/6

N2 - A novel enantioselective approach to the synthesis of a compound collection inspired by natural pyrrolizidine alkaloids was developed, employing an enantioselectively catalyzed 1,3-dipolar cycloaddition as the key step. The cycloadducts were obtained with excellent enantio- and diastereoselectivity. Biological evaluation of the resulting compound collection revealed that the compound class has multiple bioactivities, including activity against Plasmodium falciparum 3D7 and inhibition of Hedgehog signaling.

AB - A novel enantioselective approach to the synthesis of a compound collection inspired by natural pyrrolizidine alkaloids was developed, employing an enantioselectively catalyzed 1,3-dipolar cycloaddition as the key step. The cycloadducts were obtained with excellent enantio- and diastereoselectivity. Biological evaluation of the resulting compound collection revealed that the compound class has multiple bioactivities, including activity against Plasmodium falciparum 3D7 and inhibition of Hedgehog signaling.

UR - http://www.scopus.com/inward/record.url?scp=85049659032&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85049659032&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.7b03202

DO - 10.1021/acs.joc.7b03202

M3 - Article

C2 - 29460633

AN - SCOPUS:85049659032

SN - 0022-3263

VL - 83

SP - 7033

EP - 7041

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Catalytic Enantioselective Synthesis of a Pyrrolizidine-Alkaloid-Inspired Compound Collection with Antiplasmodial Activity

抄録

ASJC Scopus subject areas

文献へのアクセス

他のファイルとリンク

フィンガープリント

引用スタイル