Ring-closing metathesis: A powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors

Sylvain Lebreton; Xiao Song Xie; Deborah Ferguson; Jef K. De Brabander

doi:10.1016/j.tet.2004.06.146

Ring-closing metathesis: A powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors

Sylvain Lebreton, Xiao Song Xie, Deborah Ferguson, Jef K. De Brabander

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

24 Scopus citations

Abstract

Based on our synthetic strategy developed for the total synthesis of the macrocyclic salicylate natural product salicylihalamide, we describe herein the synthesis of a series of simplified salicylihalamide-based analogs. Alterations in the aromatic fragment, the macrolactone scaffold and side-chain were evaluated for in vitro inhibition of V-ATPase activity and human tumor cell growth. Graphical abstract.

Original language	English (US)
Pages (from-to)	9635-9647
Number of pages	13
Journal	Tetrahedron
Volume	60
Issue number	43 SPEC. ISS.
DOIs	https://doi.org/10.1016/j.tet.2004.06.146
State	Published - Oct 18 2004

Keywords

Cancer
Macrocyclic
Natural product
Olefin-metathesis
Vacuolar ATPase

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2004.06.146

Cite this

@article{386ab9d2e88a4558ae0c6d2b9cf785d3,

title = "Ring-closing metathesis: A powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors",

abstract = "Based on our synthetic strategy developed for the total synthesis of the macrocyclic salicylate natural product salicylihalamide, we describe herein the synthesis of a series of simplified salicylihalamide-based analogs. Alterations in the aromatic fragment, the macrolactone scaffold and side-chain were evaluated for in vitro inhibition of V-ATPase activity and human tumor cell growth. Graphical abstract.",

keywords = "Cancer, Macrocyclic, Natural product, Olefin-metathesis, Vacuolar ATPase",

author = "Sylvain Lebreton and Xie, {Xiao Song} and Deborah Ferguson and {De Brabander}, {Jef K.}",

note = "Funding Information: Financial support provided by the Robert A. Welch Foundation and the National Institutes of Health through grants CA 90349 and CA 95471 (J.K. De Brabander) and DK 33627 (X.-S. Xie) is gratefully acknowledged. J.K. De Brabander is a fellow of the Alfred P. Sloan Foundation.",

year = "2004",

month = oct,

day = "18",

doi = "10.1016/j.tet.2004.06.146",

language = "English (US)",

volume = "60",

pages = "9635--9647",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "43 SPEC. ISS.",

}

TY - JOUR

T1 - Ring-closing metathesis

T2 - A powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors

AU - Lebreton, Sylvain

AU - Xie, Xiao Song

AU - Ferguson, Deborah

AU - De Brabander, Jef K.

N1 - Funding Information: Financial support provided by the Robert A. Welch Foundation and the National Institutes of Health through grants CA 90349 and CA 95471 (J.K. De Brabander) and DK 33627 (X.-S. Xie) is gratefully acknowledged. J.K. De Brabander is a fellow of the Alfred P. Sloan Foundation.

PY - 2004/10/18

Y1 - 2004/10/18

N2 - Based on our synthetic strategy developed for the total synthesis of the macrocyclic salicylate natural product salicylihalamide, we describe herein the synthesis of a series of simplified salicylihalamide-based analogs. Alterations in the aromatic fragment, the macrolactone scaffold and side-chain were evaluated for in vitro inhibition of V-ATPase activity and human tumor cell growth. Graphical abstract.

AB - Based on our synthetic strategy developed for the total synthesis of the macrocyclic salicylate natural product salicylihalamide, we describe herein the synthesis of a series of simplified salicylihalamide-based analogs. Alterations in the aromatic fragment, the macrolactone scaffold and side-chain were evaluated for in vitro inhibition of V-ATPase activity and human tumor cell growth. Graphical abstract.

KW - Cancer

KW - Macrocyclic

KW - Natural product

KW - Olefin-metathesis

KW - Vacuolar ATPase

UR - http://www.scopus.com/inward/record.url?scp=4544286910&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=4544286910&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.06.146

DO - 10.1016/j.tet.2004.06.146

M3 - Article

AN - SCOPUS:4544286910

SN - 0040-4020

VL - 60

SP - 9635

EP - 9647

JO - Tetrahedron

JF - Tetrahedron

IS - 43 SPEC. ISS.

ER -

Ring-closing metathesis: A powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this