Jump to main content
Jump to site search

Issue 6, 2016
Previous Article Next Article

New hydrazones of 5-nitro-2-furaldehyde with adamantanealkanohydrazides: synthesis and in vitro trypanocidal activity

Author affiliations

Abstract

Nifurtimox, a hydrazone of 5-nitro-2-furaldehyde is used therapeutically against Trypanosoma brucei and Trypanosoma cruzi infections. Exploiting our previous observation that adamantane derivatives display trypanocidal activity, we designed and synthesised a range of hydrazones of 5-nitro-2-furaldehyde with adamantane alkanohydrazides. The most promising compounds had >20 times greater activity (IC50 ∼ 100 nM) than nifurtimox, with selectivity indices of 20–80. SAR studies revealed that activity is associated with increased lipophilicity and influenced by conformational flexibility. Derivatives lacking a nitro group were practically inactive against both parasites. The approaches described demonstrate the feasibility of enhancing the potency of chemical entities with known trypanocidal activity.

Graphical abstract: New hydrazones of 5-nitro-2-furaldehyde with adamantanealkanohydrazides: synthesis and in vitro trypanocidal activity

Back to tab navigation

Supplementary files

Article information


Submitted
18 Jan 2016
Accepted
01 May 2016
First published
11 May 2016

Med. Chem. Commun., 2016,7, 1229-1236
Article type
Research Article

New hydrazones of 5-nitro-2-furaldehyde with adamantanealkanohydrazides: synthesis and in vitro trypanocidal activity

A. Foscolos, I. Papanastasiou, G. B. Foscolos, A. Tsotinis, T. F. Kellici, T. Mavromoustakos, M. C. Taylor and J. M. Kelly, Med. Chem. Commun., 2016, 7, 1229
DOI: 10.1039/C6MD00035E

Search articles by author

Spotlight

Advertisements