Synthesis of an analog of amphidinol 3 corresponding to the c31-c67 section

Tomoyuki Koge; Yuma Wakamiya; Makoto Ebine; Tohru Oishi

doi:10.3987/COM-18-13927

Synthesis of an analog of amphidinol 3 corresponding to the c31-c67 section

Tomoyuki Koge, Yuma Wakamiya, Makoto Ebine, Tohru Oishi

Organic and Biological Chemistry

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

1 Citation (Scopus)

Abstract

An artificial analog corresponding to the C31-C67 section of amphidinol 3 (AM3) was designed as a part of the structure-activity relationship studies to elucidate structure requirements for eliciting antifungal activity. To reduce the number of synthetic steps, the 43-deoxy-51-epi derivative containing common tetrahydropyran ring system was designed and synthesized from a pivotal intermediate in 17 steps. The analog elicited no antifungal activity, suggesting that not only the two tetrahydropyran rings, but also polyol section of AM3 are necessary to elicit antifungal activity.

Original language	English
Pages (from-to)	1197-1202
Number of pages	6
Journal	Heterocycles
Volume	96
Issue number	7
DOIs	https://doi.org/10.3987/COM-18-13927
Publication status	Published - 2018

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-18-13927

Cite this

@article{8374c7b9c8894628a897bfe6c6c30d6b,

title = "Synthesis of an analog of amphidinol 3 corresponding to the c31-c67 section",

abstract = "An artificial analog corresponding to the C31-C67 section of amphidinol 3 (AM3) was designed as a part of the structure-activity relationship studies to elucidate structure requirements for eliciting antifungal activity. To reduce the number of synthetic steps, the 43-deoxy-51-epi derivative containing common tetrahydropyran ring system was designed and synthesized from a pivotal intermediate in 17 steps. The analog elicited no antifungal activity, suggesting that not only the two tetrahydropyran rings, but also polyol section of AM3 are necessary to elicit antifungal activity.",

author = "Tomoyuki Koge and Yuma Wakamiya and Makoto Ebine and Tohru Oishi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP24750092, JP15K17857, JP15K13645, Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP24750092, JP15K17857, JP15K13645, and JP16H01159 in Middle Molecular Strategy. Publisher Copyright: {\textcopyright} 2018 The Japan Institute of Heterocyclic Chemistry.",

year = "2018",

doi = "10.3987/COM-18-13927",

language = "English",

volume = "96",

pages = "1197--1202",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "7",

}

TY - JOUR

T1 - Synthesis of an analog of amphidinol 3 corresponding to the c31-c67 section

AU - Koge, Tomoyuki

AU - Wakamiya, Yuma

AU - Ebine, Makoto

AU - Oishi, Tohru

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP24750092, JP15K17857, JP15K13645, Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP24750092, JP15K17857, JP15K13645, and JP16H01159 in Middle Molecular Strategy. Publisher Copyright: © 2018 The Japan Institute of Heterocyclic Chemistry.

PY - 2018

Y1 - 2018

N2 - An artificial analog corresponding to the C31-C67 section of amphidinol 3 (AM3) was designed as a part of the structure-activity relationship studies to elucidate structure requirements for eliciting antifungal activity. To reduce the number of synthetic steps, the 43-deoxy-51-epi derivative containing common tetrahydropyran ring system was designed and synthesized from a pivotal intermediate in 17 steps. The analog elicited no antifungal activity, suggesting that not only the two tetrahydropyran rings, but also polyol section of AM3 are necessary to elicit antifungal activity.

AB - An artificial analog corresponding to the C31-C67 section of amphidinol 3 (AM3) was designed as a part of the structure-activity relationship studies to elucidate structure requirements for eliciting antifungal activity. To reduce the number of synthetic steps, the 43-deoxy-51-epi derivative containing common tetrahydropyran ring system was designed and synthesized from a pivotal intermediate in 17 steps. The analog elicited no antifungal activity, suggesting that not only the two tetrahydropyran rings, but also polyol section of AM3 are necessary to elicit antifungal activity.

UR - http://www.scopus.com/inward/record.url?scp=85050863704&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85050863704&partnerID=8YFLogxK

U2 - 10.3987/COM-18-13927

DO - 10.3987/COM-18-13927

M3 - Article

AN - SCOPUS:85050863704

SN - 0385-5414

VL - 96

SP - 1197

EP - 1202

JO - Heterocycles

JF - Heterocycles

IS - 7

ER -

Synthesis of an analog of amphidinol 3 corresponding to the c31-c67 section

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this