Design and preparation of sterol mimetics as potential antiparasitics

Federica Gigante; Marcel Kaiser; Reto Brun; Ian H. Gilbert

doi:10.1016/j.bmc.2010.08.007

Design and preparation of sterol mimetics as potential antiparasitics

Federica Gigante, Marcel Kaiser, Reto Brun, Ian H. Gilbert

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

7 Citations (Scopus)

Abstract

We have previously shown that azasterols have activity against Trypanosoma brucei, Trypanosoma cruzi and Leishmania species, which are the causative agents of various neglected tropical diseases. In this paper, we discuss the replacement of the sterol core of the azasterols with sterol mimics. Various mimics were designed, and the structures were minimised to see if they could adopt a similar conformation to that of the azasterols. From this, two series of mimics were synthesised and then evaluated against the parasites. Compounds showed moderate activity. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7291-7301
Number of pages	11
Journal	Bioorganic & Medicinal Chemistry
Volume	18
Issue number	20
DOIs	https://doi.org/10.1016/j.bmc.2010.08.007
Publication status	Published - 15 Oct 2010

Keywords

Trypanosoma
Leishmania
Azasterol
HIGH-ENERGY INTERMEDIATE
ESTROGEN-RECEPTOR
TRYPANOSOMA-BRUCEI
AZASTEROLS
INHIBITION
ANALOGS
METHYLTRANSFERASE
BIOSYNTHESIS
DERIVATIVES
BINDING

UN SDGs

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

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10.1016/j.bmc.2010.08.007

Cite this

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title = "Design and preparation of sterol mimetics as potential antiparasitics",

abstract = "We have previously shown that azasterols have activity against Trypanosoma brucei, Trypanosoma cruzi and Leishmania species, which are the causative agents of various neglected tropical diseases. In this paper, we discuss the replacement of the sterol core of the azasterols with sterol mimics. Various mimics were designed, and the structures were minimised to see if they could adopt a similar conformation to that of the azasterols. From this, two series of mimics were synthesised and then evaluated against the parasites. Compounds showed moderate activity. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "Trypanosoma, Leishmania, Azasterol, HIGH-ENERGY INTERMEDIATE, ESTROGEN-RECEPTOR, TRYPANOSOMA-BRUCEI, AZASTEROLS, INHIBITION, ANALOGS, METHYLTRANSFERASE, BIOSYNTHESIS, DERIVATIVES, BINDING",

author = "Federica Gigante and Marcel Kaiser and Reto Brun and Gilbert, {Ian H.}",

year = "2010",

month = oct,

day = "15",

doi = "10.1016/j.bmc.2010.08.007",

language = "English",

volume = "18",

pages = "7291--7301",

journal = "Bioorganic & Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier",

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TY - JOUR

T1 - Design and preparation of sterol mimetics as potential antiparasitics

AU - Gigante, Federica

AU - Kaiser, Marcel

AU - Brun, Reto

AU - Gilbert, Ian H.

PY - 2010/10/15

Y1 - 2010/10/15

N2 - We have previously shown that azasterols have activity against Trypanosoma brucei, Trypanosoma cruzi and Leishmania species, which are the causative agents of various neglected tropical diseases. In this paper, we discuss the replacement of the sterol core of the azasterols with sterol mimics. Various mimics were designed, and the structures were minimised to see if they could adopt a similar conformation to that of the azasterols. From this, two series of mimics were synthesised and then evaluated against the parasites. Compounds showed moderate activity. (C) 2010 Elsevier Ltd. All rights reserved.

AB - We have previously shown that azasterols have activity against Trypanosoma brucei, Trypanosoma cruzi and Leishmania species, which are the causative agents of various neglected tropical diseases. In this paper, we discuss the replacement of the sterol core of the azasterols with sterol mimics. Various mimics were designed, and the structures were minimised to see if they could adopt a similar conformation to that of the azasterols. From this, two series of mimics were synthesised and then evaluated against the parasites. Compounds showed moderate activity. (C) 2010 Elsevier Ltd. All rights reserved.

KW - Trypanosoma

KW - Leishmania

KW - Azasterol

KW - HIGH-ENERGY INTERMEDIATE

KW - ESTROGEN-RECEPTOR

KW - TRYPANOSOMA-BRUCEI

KW - AZASTEROLS

KW - INHIBITION

KW - ANALOGS

KW - METHYLTRANSFERASE

KW - BIOSYNTHESIS

KW - DERIVATIVES

KW - BINDING

U2 - 10.1016/j.bmc.2010.08.007

DO - 10.1016/j.bmc.2010.08.007

M3 - Article

C2 - 20846867

SN - 0968-0896

VL - 18

SP - 7291

EP - 7301

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 20

ER -

Design and preparation of sterol mimetics as potential antiparasitics

Abstract

Keywords

UN SDGs

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