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Molecules 2016, 21(6), 802; doi:10.3390/molecules21060802

Antileishmanial Activity and Structure-Activity Relationship of Triazolic Compounds Derived from the Neolignans Grandisin, Veraguensin, and Machilin G

1
Laboratório de Parasitologia Humana, Centro de Ciências Biológicas e da Saúde, Universidade Federal de Mato Grosso do Sul, 79090-900 Campo Grande—MS, Brazil
2
Laboratório de Síntese e Química Medicinal-LASQUIM, Centro de Ciências Biológicas e da Saúde, Universidade Federal de Mato Grosso do Sul, 79090-900 Campo Grande—MS, Brazil
3
Laboratório de Biologia Molecular e Culturas Celulares, Centro de Ciências Biológicas e da Saúde, Universidade Federal de Mato Grosso do Sul, 79090-900 Campo Grande—MS, Brazil
4
Laboratório de Biofisiofarmacologia, Centro de Ciências Biológicas e da Saúde, Universidade Federal de Mato Grosso do Sul, 79090-900 Campo Grande—MS, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Marcello Iriti
Received: 26 May 2016 / Revised: 15 June 2016 / Accepted: 16 June 2016 / Published: 20 June 2016
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Abstract

Sixteen 1,4-diaryl-1,2,3-triazole compounds 419 derived from the tetrahydrofuran neolignans veraguensin 1, grandisin 2, and machilin G 3 were tested against Leishmania (Leishmania) amazonensis intracellular amastigotes. Triazole compounds 419 were synthetized via Click Chemistry strategy by 1,3-dipolar cycloaddition between terminal acetylenes and aryl azides containing methoxy and methylenedioxy groups as substituents. Our results suggest that most derivatives were active against intracellular amastigotes, with IC50 values ranging from 4.4 to 32.7 µM. The index of molecular hydrophobicity (ClogP) ranged from 2.8 to 3.4, reflecting a lipophilicity/hydrosolubility rate suitable for transport across membranes, which may have resulted in the potent antileishmanial activity observed. Regarding structure-activity relationship (SAR), compounds 14 and 19, containing a trimethoxy group, were the most active (IC50 values of 5.6 and 4.4 µM, respectively), with low cytotoxicity on mammalian cells (SI = 14.1 and 10.6). These compounds induced nitric oxide production by the host macrophage cells, which could be suggested as the mechanism involved in the intracellular killing of parasites. These results would be useful for the planning of new derivatives with higher antileishmanial activities. View Full-Text
Keywords: neglected diseases; biological activity; cytotoxicity; synthetic compounds; neolignan derivatives neglected diseases; biological activity; cytotoxicity; synthetic compounds; neolignan derivatives
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Costa, E.C.; Cassamale, T.B.; Carvalho, D.B.; Bosquiroli, L.S.S.; Ojeda, M.; Ximenes, T.V.; Matos, M.F.C.; Kadri, M.C.T.; Baroni, A.C.M.; Arruda, C.C.P. Antileishmanial Activity and Structure-Activity Relationship of Triazolic Compounds Derived from the Neolignans Grandisin, Veraguensin, and Machilin G. Molecules 2016, 21, 802.

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