Effect of isoxazole derivatives of tetrahydrofuran neolignans on intracellular amastigotes of Leishmania (Leishmania) amazonensis: A structure-activity relationship (SAR) comparative study with triazole-neolignan-based compounds.

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ID: 14834
2019
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Abstract
Isoxazole analogues derived from the neolignans veraguensin, grandisin, and machilin G were previously synthesized with different substitution patterns through the bioisosterism strategy. These compounds were tested on intracellular amastigotes of Leishmania (Leishmania) amazonensis; the derivatives proved to be active against intracellular amastigotes, with IC values ranging from 0.4 to 25 μM. The most active analogues were 4', 14', 15' and 18', with IC values of 0.9 μM, 0.4 μM, 0.7 μM and 1.4 μM respectively, showing high selectivity indexes (SI = 277.0; 625.0; 178.5 and 357.1). Overall, the isoxazole analogues did not induce nitric oxide (NO) production by infected cells; there was no evidence that NO influences the antileishmanial mechanism of action, except for compound 4'. Trimethoxy groups as substituents seemed to be critical for antileishmanial activity. The SAR study demonstrated that the isoxazole compounds were more active than 1,2,3-triazole compounds with the same substitution partners, demonstrating the importance of the bioisosterism strategy in drug design.
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Authors das Neves, Amarith R;Trefzger, Ozildéia S;Barbosa, Natália V;Honorato, Antonio M;Carvalho, Diego B;Moslaves, Iluska S;Kadri, Mônica C T;Yoshida, Nidia C;Kato, Massuo J;Arruda, Carla C P;Baroni, Adriano C M;
Journal Chemical biology & drug design
Year 2019
DOI
10.1111/cbdd.13609
URL
Keywords Keywords not found

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