Novel spirobicyclic artemisinin analogues (artemalogues): Synthesis and antitumor activities

Gang Liu; Shanshan Song; Shiqi Shu; Zehong Miao; Ao Zhang; Chunyong Ding

doi:10.1016/j.ejmech.2015.08.035

Novel spirobicyclic artemisinin analogues (artemalogues): Synthesis and antitumor activities

Gang Liu, Shanshan Song, Shiqi Shu, Zehong Miao, Ao Zhang, Chunyong Ding

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

28 Scopus citations

Abstract

The sesquiterpene lactone framework of artemisinin was used as a drug repositioning prototype for the development of novel antitumor drugs. Several series of novel artemisinin analogues (artemalogues) were designed and synthesized through 1,3-dipolar cycloaddition of artemisitene with nitrile oxides or nitrones. The isoxazolidine-containing spirobicyclic artemalogue 11b turns out to be the most potent with low micromolar IC₅₀ values against all three tumor cells, which were at least 4-to 14-fold more potent than the parent artemisinin.

Original language	English (US)
Pages (from-to)	17-28
Number of pages	12
Journal	European journal of medicinal chemistry
Volume	103
DOIs	https://doi.org/10.1016/j.ejmech.2015.08.035
State	Published - Oct 20 2015
Externally published	Yes

Keywords

1 3-dipolar cycloaddition
Antiprolifereative effect
Artemisinin
Spirobicyclic artemalogues
Stereoconfiguration

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2015.08.035

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title = "Novel spirobicyclic artemisinin analogues (artemalogues): Synthesis and antitumor activities",

abstract = "The sesquiterpene lactone framework of artemisinin was used as a drug repositioning prototype for the development of novel antitumor drugs. Several series of novel artemisinin analogues (artemalogues) were designed and synthesized through 1,3-dipolar cycloaddition of artemisitene with nitrile oxides or nitrones. The isoxazolidine-containing spirobicyclic artemalogue 11b turns out to be the most potent with low micromolar IC50 values against all three tumor cells, which were at least 4-to 14-fold more potent than the parent artemisinin.",

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T2 - Synthesis and antitumor activities

AU - Liu, Gang

AU - Song, Shanshan

AU - Shu, Shiqi

AU - Miao, Zehong

AU - Zhang, Ao

AU - Ding, Chunyong

PY - 2015/10/20

Y1 - 2015/10/20

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KW - 1 3-dipolar cycloaddition

KW - Antiprolifereative effect

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KW - Spirobicyclic artemalogues

KW - Stereoconfiguration

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Novel spirobicyclic artemisinin analogues (artemalogues): Synthesis and antitumor activities

Abstract

Keywords

ASJC Scopus subject areas

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