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Design, Synthesis, and Trypanocidal Activity of Novel 5‐Nitroimidazolyl O ‐Benzyloxime Ethers
Author(s) -
Carvalho Samir Aquino,
Osorio Luis Felipe Baumotte,
Salomão Kelly,
Castro Solange Lisboa,
Wardell Solange M. S. V.,
Wardell James Lewis,
Silva Edson Ferreira,
Fraga Carlos Alberto Manssour
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2989
Subject(s) - benznidazole , trypanosoma cruzi , chemistry , nitroimidazole , antiprotozoal , trypanocidal agent , chagas disease , stereochemistry , imidazole , oxime , ether , combinatorial chemistry , medicinal chemistry , organic chemistry , trypanosoma brucei , biochemistry , in vitro , biology , parasite hosting , world wide web , computer science , gene , immunology
In this paper, we describe the synthesis and the action against of the trypomastigote form of Trypanosoma cruzi of a new class of nitroimidazole‐2‐carbaldehyde O ‐benzyloximes. These derivatives were designed through the application of molecular hybridization concept between two potent antiprotozoal compounds, the 5‐nitrothiophene‐2‐carbaldehyde O ‐oxime 6 and the trypanocidal piperidinyl‐4‐carbaldehyde O ‐benzyloxime 7 with the intention of reaching two distinct molecular targets of T. cruzi . The activity of these benzyl ether derivatives was tested against the infective trypomastigote forms of T. cruzi , and the derivative ( E )‐1‐methyl‐5‐nitro‐1 H ‐imidazole‐2‐carbaldehyde O ‐(4‐nitrobenzyl) oxime ( 1 ) presented moderate trypanocidal activity (IC 50 = 12.7 μ M ) when compared with the standard drug benznidazole, which showed to be a good starting point for the design of more effective trypanocide agents.
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