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Synthesis and Evaluation of Nifurtimox–Adamantane Adducts with Trypanocidal Activity
Author(s) -
Foscolos AngelikiSofia,
Papanastasiou Ioannis,
Tsotinis Andrew,
Taylor Martin C.,
Kelly John M.
Publication year - 2019
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201900165
Subject(s) - adamantane , chemistry , selectivity , methylene , stereochemistry , adduct , nitrofuran , hydrazone , nifurtimox , medicinal chemistry , combinatorial chemistry , organic chemistry , trypanosoma cruzi , biology , parasite hosting , world wide web , computer science , genetics , catalysis
The synthesis and pharmacological evaluation of C1‐substituted adamantane hydrazones, their C2‐substituted isomers, and C1‐substituted adamantane furanoic carboxamides is described. These new adamantane derivatives exhibited an interesting pharmacological profile in terms of trypanocidal activity and selectivity. The most active adduct with the best selectivity in this study was found to be the phenylacetoxy hydrazone 1 b (2‐[4‐(tricyclo[3.3.1.1 3,7 ]dec‐1‐yl)phenyl]‐ N′ ‐[(5‐nitrofuran‐2‐yl)methylene]acetohydrazide; EC 50 =11±0.9 n m , SI Tb =770).