Catalytic asymmetric synthesis of mixed 3,3′-bisindoles and their evaluation as Wnt signaling inhibitors

Takayoshi Arai; Yushi Yamamoto; Atsuko Awata; Kentaro Kamiya; Masami Ishibashi; Midori A. Arai

doi:10.1002/anie.201208918

Catalytic asymmetric synthesis of mixed 3,3′-bisindoles and their evaluation as Wnt signaling inhibitors

Takayoshi Arai, Yushi Yamamoto, Atsuko Awata, Kentaro Kamiya, Masami Ishibashi, Midori A. Arai

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

81 Citations (Scopus)

Abstract

TOP class: The first efficient catalytic asymmetric coupling reaction of indoles with isatin-derived nitroalkenes was accomplished by using a complex consisting of a chiral imidazoline aminophenol ligand (1; see scheme) and Cu(OTf)₂. Biological activity of the newly formed chiral 3,3′-bisindoles was also confirmed in a Wnt signaling inhibitory assay.

Original language	English
Pages (from-to)	2486-2490
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	9
DOIs	https://doi.org/10.1002/anie.201208918
Publication status	Published - 2013 Feb 25
Externally published	Yes

Keywords

1,4-addition
asymmetric synthesis
bisindole
homogeneous catalysis
wnt signal

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201208918

Cite this

@article{2ab10e9b9cd94d3392bc30c6e7e5a7de,

title = "Catalytic asymmetric synthesis of mixed 3,3′-bisindoles and their evaluation as Wnt signaling inhibitors",

abstract = "TOP class: The first efficient catalytic asymmetric coupling reaction of indoles with isatin-derived nitroalkenes was accomplished by using a complex consisting of a chiral imidazoline aminophenol ligand (1; see scheme) and Cu(OTf)2. Biological activity of the newly formed chiral 3,3′-bisindoles was also confirmed in a Wnt signaling inhibitory assay.",

keywords = "1,4-addition, asymmetric synthesis, bisindole, homogeneous catalysis, wnt signal",

author = "Takayoshi Arai and Yushi Yamamoto and Atsuko Awata and Kentaro Kamiya and Masami Ishibashi and Arai, {Midori A.}",

year = "2013",

month = feb,

day = "25",

doi = "10.1002/anie.201208918",

language = "English",

volume = "52",

pages = "2486--2490",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "9",

}

TY - JOUR

T1 - Catalytic asymmetric synthesis of mixed 3,3′-bisindoles and their evaluation as Wnt signaling inhibitors

AU - Arai, Takayoshi

AU - Yamamoto, Yushi

AU - Awata, Atsuko

AU - Kamiya, Kentaro

AU - Ishibashi, Masami

AU - Arai, Midori A.

PY - 2013/2/25

Y1 - 2013/2/25

N2 - TOP class: The first efficient catalytic asymmetric coupling reaction of indoles with isatin-derived nitroalkenes was accomplished by using a complex consisting of a chiral imidazoline aminophenol ligand (1; see scheme) and Cu(OTf)2. Biological activity of the newly formed chiral 3,3′-bisindoles was also confirmed in a Wnt signaling inhibitory assay.

AB - TOP class: The first efficient catalytic asymmetric coupling reaction of indoles with isatin-derived nitroalkenes was accomplished by using a complex consisting of a chiral imidazoline aminophenol ligand (1; see scheme) and Cu(OTf)2. Biological activity of the newly formed chiral 3,3′-bisindoles was also confirmed in a Wnt signaling inhibitory assay.

KW - 1,4-addition

KW - asymmetric synthesis

KW - bisindole

KW - homogeneous catalysis

KW - wnt signal

UR - http://www.scopus.com/inward/record.url?scp=84874249419&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84874249419&partnerID=8YFLogxK

U2 - 10.1002/anie.201208918

DO - 10.1002/anie.201208918

M3 - Article

C2 - 23355386

AN - SCOPUS:84874249419

SN - 1433-7851

VL - 52

SP - 2486

EP - 2490

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 9

ER -

Catalytic asymmetric synthesis of mixed 3,3′-bisindoles and their evaluation as Wnt signaling inhibitors

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this