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Clotrimazole scaffold as an innovative pharmacophore towards potent antimalarial agents: design, synthesis, and biological and structure-activity relationship studies.

Abstract：

:We describe herein the design, synthesis, biological evaluation, and structure-activity relationship (SAR) studies of an innovative class of antimalarial agents based on a polyaromatic pharmacophore structurally related to clotrimazole and easy to synthesize by low-cost synthetic procedures. SAR studies delineated a number of structural features able to modulate the in vitro and in vivo antimalarial activity. A selected set of antimalarials was further biologically investigated and displayed low in vitro toxicity on a panel of human and murine cell lines. In vitro, the novel compounds proved to be selective for free heme, as demonstrated in the beta-hematin inhibitory activity assay, and did not show inhibitory activity against 14-alpha-lanosterol demethylase (a fungal P450 cytochrome). Compounds 2, 4e, and 4n exhibited in vivo activity against P. chabaudi after oral administration and thus represent promising antimalarial agents for further preclinical development.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Gemma S,Campiani G,Butini S,Kukreja G,Coccone SS,Joshi BP,Persico M,Nacci V,Fiorini I,Novellino E,Fattorusso E,Taglialatela-Scafati O,Savini L,Taramelli D,Basilico N,Parapini S,Morace G,Yardley V,Croft S,Coletta M,

doi

10.1021/jm701247k

subject

Has Abstract

pub_date

2008-03-13 00:00:00

pages

1278-94

issue

5

eissn

0022-2623

issn

1520-4804

journal_volume

51

pub_type

杂志文章

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