Synthesis and anticancer activity of polyhydroxylated 18-membered analogue of antimycin A 3

Ade Arsianti; Hiroki Tanimoto; Tsumoru Morimoto; Anton Bahtiar; Tatsuo Takeya; Kiyomi Kakiuchi

doi:10.1016/j.tet.2012.01.080

Synthesis and anticancer activity of polyhydroxylated 18-membered analogue of antimycin A ₃

Ade Arsianti^*, Hiroki Tanimoto, Tsumoru Morimoto, Anton Bahtiar, Tatsuo Takeya, Kiyomi Kakiuchi

^*Corresponding author for this work

Biorecognition Chemistry

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

13 Scopus citations

Abstract

A novel polyhydroxylated 18-membered analogue of antimycin A ₃ was synthesized. Our synthesis commenced with Boc-l-threonine and was achieved by way of one-pot homocoupling/ring-closing olefin metathesis reaction cascade and Sharpless asymmetric dihydroxylation. The analogue exhibited a greater anticancer activity against HeLa cells, breast MDA-MB-231 cells, and prostate PC-3 cells compared to the original antimycin A ₃.

Original language	English
Pages (from-to)	2884-2891
Number of pages	8
Journal	Tetrahedron
Volume	68
Issue number	13
DOIs	https://doi.org/10.1016/j.tet.2012.01.080
State	Published - 2012/04/01

Keywords

Analogue
Anticancer
Antimycin A
Polyhydroxylated 18-membered ring
Synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2012.01.080

Cite this

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title = "Synthesis and anticancer activity of polyhydroxylated 18-membered analogue of antimycin A 3 ",

abstract = "A novel polyhydroxylated 18-membered analogue of antimycin A 3 was synthesized. Our synthesis commenced with Boc-l-threonine and was achieved by way of one-pot homocoupling/ring-closing olefin metathesis reaction cascade and Sharpless asymmetric dihydroxylation. The analogue exhibited a greater anticancer activity against HeLa cells, breast MDA-MB-231 cells, and prostate PC-3 cells compared to the original antimycin A 3.",

keywords = "Analogue, Anticancer, Antimycin A, Polyhydroxylated 18-membered ring, Synthesis",

author = "Ade Arsianti and Hiroki Tanimoto and Tsumoru Morimoto and Anton Bahtiar and Tatsuo Takeya and Kiyomi Kakiuchi",

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T1 - Synthesis and anticancer activity of polyhydroxylated 18-membered analogue of antimycin A 3

AU - Arsianti, Ade

AU - Tanimoto, Hiroki

AU - Morimoto, Tsumoru

AU - Bahtiar, Anton

AU - Takeya, Tatsuo

AU - Kakiuchi, Kiyomi

PY - 2012/4/1

Y1 - 2012/4/1

N2 - A novel polyhydroxylated 18-membered analogue of antimycin A 3 was synthesized. Our synthesis commenced with Boc-l-threonine and was achieved by way of one-pot homocoupling/ring-closing olefin metathesis reaction cascade and Sharpless asymmetric dihydroxylation. The analogue exhibited a greater anticancer activity against HeLa cells, breast MDA-MB-231 cells, and prostate PC-3 cells compared to the original antimycin A 3.

AB - A novel polyhydroxylated 18-membered analogue of antimycin A 3 was synthesized. Our synthesis commenced with Boc-l-threonine and was achieved by way of one-pot homocoupling/ring-closing olefin metathesis reaction cascade and Sharpless asymmetric dihydroxylation. The analogue exhibited a greater anticancer activity against HeLa cells, breast MDA-MB-231 cells, and prostate PC-3 cells compared to the original antimycin A 3.

KW - Analogue

KW - Anticancer

KW - Antimycin A

KW - Polyhydroxylated 18-membered ring

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=84857910377&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.01.080

DO - 10.1016/j.tet.2012.01.080

M3 - 学術論文

AN - SCOPUS:84857910377

SN - 0040-4020

VL - 68

SP - 2884

EP - 2891

JO - Tetrahedron

JF - Tetrahedron

IS - 13

ER -