Synthesis and biological activity of mycalolide analogs

Kiyotake Suenaga; Tomoyuki Kimura; Takeshi Kuroda; Keita Matsui; Saori Miya; Satomi Kuribayashi; Akira Sakakura; Hideo Kigoshi

doi:10.1016/j.tet.2006.06.046

Synthesis and biological activity of mycalolide analogs

Kiyotake Suenaga, Tomoyuki Kimura, Takeshi Kuroda, Keita Matsui, Saori Miya, Satomi Kuribayashi, Akira Sakakura, Hideo Kigoshi

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

27 Citations (Scopus)

Abstract

Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), a trisoxazole macrolide of marine origin, was stereoselectively synthesized using Roush crotylboration, an Evans aldol reaction, and a Paterson aldol reaction as key steps. The analog 4 was found to have strong actin-depolymerizing activity.

Original language	English
Pages (from-to)	8278-8290
Number of pages	13
Journal	Tetrahedron
Volume	62
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2006.06.046
Publication status	Published - 2006 Aug 28
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

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

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10.1016/j.tet.2006.06.046

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title = "Synthesis and biological activity of mycalolide analogs",

abstract = "Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), a trisoxazole macrolide of marine origin, was stereoselectively synthesized using Roush crotylboration, an Evans aldol reaction, and a Paterson aldol reaction as key steps. The analog 4 was found to have strong actin-depolymerizing activity.",

author = "Kiyotake Suenaga and Tomoyuki Kimura and Takeshi Kuroda and Keita Matsui and Saori Miya and Satomi Kuribayashi and Akira Sakakura and Hideo Kigoshi",

note = "Funding Information: We are grateful to Professors Hiroshi Ozaki and Masatoshi Hori (The University of Tokyo) for their donation of actin and their helpful advice and discussions. This study was supported in part by the 21st Century COE program and Grants-in-Aid for Scientific Research from Ministry of Education, Culture, Sports, Science and Technology, The Asahi Glass Foundation, Suntory Institute for Bioorganic Research, Astellas Foundation for Research on Medicinal Resources, Shorai Foundation for Science and Technology, TARA project (University of Tsukuba), and Research Fellowships of the Japan Society for the Promotion of Science for Young Scientists (JSPS) to T.K. Finally, we thank Ms. Shoko Ueda, Mr. Tomohisa Handa, and Mr. Kengo Kanematsu for their technical assistance.",

year = "2006",

month = aug,

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doi = "10.1016/j.tet.2006.06.046",

language = "English",

volume = "62",

pages = "8278--8290",

journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis and biological activity of mycalolide analogs

AU - Suenaga, Kiyotake

AU - Kimura, Tomoyuki

AU - Kuroda, Takeshi

AU - Matsui, Keita

AU - Miya, Saori

AU - Kuribayashi, Satomi

AU - Sakakura, Akira

AU - Kigoshi, Hideo

N1 - Funding Information: We are grateful to Professors Hiroshi Ozaki and Masatoshi Hori (The University of Tokyo) for their donation of actin and their helpful advice and discussions. This study was supported in part by the 21st Century COE program and Grants-in-Aid for Scientific Research from Ministry of Education, Culture, Sports, Science and Technology, The Asahi Glass Foundation, Suntory Institute for Bioorganic Research, Astellas Foundation for Research on Medicinal Resources, Shorai Foundation for Science and Technology, TARA project (University of Tsukuba), and Research Fellowships of the Japan Society for the Promotion of Science for Young Scientists (JSPS) to T.K. Finally, we thank Ms. Shoko Ueda, Mr. Tomohisa Handa, and Mr. Kengo Kanematsu for their technical assistance.

PY - 2006/8/28

Y1 - 2006/8/28

N2 - Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), a trisoxazole macrolide of marine origin, was stereoselectively synthesized using Roush crotylboration, an Evans aldol reaction, and a Paterson aldol reaction as key steps. The analog 4 was found to have strong actin-depolymerizing activity.

AB - Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), a trisoxazole macrolide of marine origin, was stereoselectively synthesized using Roush crotylboration, an Evans aldol reaction, and a Paterson aldol reaction as key steps. The analog 4 was found to have strong actin-depolymerizing activity.

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JO - Tetrahedron

JF - Tetrahedron

IS - 35

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Synthesis and biological activity of mycalolide analogs

Abstract

ASJC Scopus subject areas

UN SDGs

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