Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities

Midori A. Arai; Yuuki Kofuji; Yuuki Tanaka; Natsuki Yanase; Kazuki Yamaku; Rolly G. Fuentes; Utpal Kumar Karmakar; Masami Ishibashi

doi:10.1039/c5ob02537k

Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities

Midori A. Arai, Yuuki Kofuji, Yuuki Tanaka, Natsuki Yanase, Kazuki Yamaku, Rolly G. Fuentes, Utpal Kumar Karmakar, Masami Ishibashi

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

11 Citations (Scopus)

Abstract

Rocaglamides are bioactive natural compounds which have a cyclopenta[b]benzofuran core structure. The total synthesis of a reported natural product, 3′-hydroxymethylrocaglate (5), was achieved using [3 + 2] cycloaddition between 3-hydroxyflavone and methyl cinnamate. We also describe the synthesis of rocaglamide heterocycle derivatives and evaluate their Wnt signal inhibitory activities. Compounds 4, 5, 22a, 22b, 22c and 23c showed potent Wnt signal inhibitory activity.

Original language	English
Pages (from-to)	3061-3068
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	11
DOIs	https://doi.org/10.1039/c5ob02537k
Publication status	Published - 2016
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/c5ob02537k

Cite this

@article{8d91ea7db95b48cd8ce5a1356187b8b3,

title = "Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities",

abstract = "Rocaglamides are bioactive natural compounds which have a cyclopenta[b]benzofuran core structure. The total synthesis of a reported natural product, 3′-hydroxymethylrocaglate (5), was achieved using [3 + 2] cycloaddition between 3-hydroxyflavone and methyl cinnamate. We also describe the synthesis of rocaglamide heterocycle derivatives and evaluate their Wnt signal inhibitory activities. Compounds 4, 5, 22a, 22b, 22c and 23c showed potent Wnt signal inhibitory activity.",

author = "Arai, {Midori A.} and Yuuki Kofuji and Yuuki Tanaka and Natsuki Yanase and Kazuki Yamaku and Fuentes, {Rolly G.} and Karmakar, {Utpal Kumar} and Masami Ishibashi",

note = "Funding Information: This study was supported by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS), a Grant-in-Aid for Scientific Research on Innovative Areas {"}Chemical Biology of Natural Products{"} from The Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT), the Naito Foundation, the Tokyo Biochemical Research Foundation, and by a Workshop on Chirality at Chiba University (WCCU). This work was inspired by the international and interdisciplinary environment of the Asian Core Program (JSPS), {"}Asian Chemical Biology Initiative{"}. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

doi = "10.1039/c5ob02537k",

language = "English",

volume = "14",

pages = "3061--3068",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "11",

}

TY - JOUR

T1 - Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities

AU - Arai, Midori A.

AU - Kofuji, Yuuki

AU - Tanaka, Yuuki

AU - Yanase, Natsuki

AU - Yamaku, Kazuki

AU - Fuentes, Rolly G.

AU - Karmakar, Utpal Kumar

AU - Ishibashi, Masami

N1 - Funding Information: This study was supported by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS), a Grant-in-Aid for Scientific Research on Innovative Areas "Chemical Biology of Natural Products" from The Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT), the Naito Foundation, the Tokyo Biochemical Research Foundation, and by a Workshop on Chirality at Chiba University (WCCU). This work was inspired by the international and interdisciplinary environment of the Asian Core Program (JSPS), "Asian Chemical Biology Initiative". Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016

Y1 - 2016

N2 - Rocaglamides are bioactive natural compounds which have a cyclopenta[b]benzofuran core structure. The total synthesis of a reported natural product, 3′-hydroxymethylrocaglate (5), was achieved using [3 + 2] cycloaddition between 3-hydroxyflavone and methyl cinnamate. We also describe the synthesis of rocaglamide heterocycle derivatives and evaluate their Wnt signal inhibitory activities. Compounds 4, 5, 22a, 22b, 22c and 23c showed potent Wnt signal inhibitory activity.

AB - Rocaglamides are bioactive natural compounds which have a cyclopenta[b]benzofuran core structure. The total synthesis of a reported natural product, 3′-hydroxymethylrocaglate (5), was achieved using [3 + 2] cycloaddition between 3-hydroxyflavone and methyl cinnamate. We also describe the synthesis of rocaglamide heterocycle derivatives and evaluate their Wnt signal inhibitory activities. Compounds 4, 5, 22a, 22b, 22c and 23c showed potent Wnt signal inhibitory activity.

UR - http://www.scopus.com/inward/record.url?scp=84960346608&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84960346608&partnerID=8YFLogxK

U2 - 10.1039/c5ob02537k

DO - 10.1039/c5ob02537k

M3 - Article

C2 - 26893289

AN - SCOPUS:84960346608

SN - 1477-0520

VL - 14

SP - 3061

EP - 3068

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 11

ER -

Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this