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Synthesis of conformationally constrained adamantane imidazolines with trypanocidal activity
Author(s) -
Papanastasiou Ioannis,
Tsotinis Andrew,
Foscolos George B.,
Prathalingam S. Radhika,
Kelly John M.
Publication year - 2008
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.5570450524
Subject(s) - rimantadine , adamantane , chemistry , amidine , trypanosoma brucei , stereochemistry , combinatorial chemistry , trypanocidal agent , bicyclic molecule , potency , organic chemistry , in vitro , biochemistry , virology , virus , influenza a virus , gene , biology
Aiming at the development of new adamantano building blocks for treating African trypanosomiasis, we report on the synthesis of spiro adamantane 2‐imidazolines 8a‐f and 9a‐c , and their congeneric 5‐(1‐adamantyl)imidazolines 14 and 15 . The potency of these compounds against Trypanosoma brucei was compared to that of rimantadine and found, in the case of compound 14e , to be three fold higher. Together with the other active compounds, 14b and 15b , which were equipotent to rimantadine, the new molecules illustrate the synergistic effect of the lipophilic character of adamantane and the C1 amidine functionality on trypanocidal activity.