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Design, synthesis and identification of novel molecular hybrids based on naphthoquinone aromatic hydrazides as potential trypanocide and leishmanicidal agents

Authors :
ROSANE D. CEZAR
ADRIANO O. DA SILVA
ROSÂNGELA S. LOPES
CELSO V. NAKAMURA
JEAN HENRIQUE S. RODRIGUES
ESTELA MARIANA G. LOURENÇO
SUMBAL SABA
ADILSON BEATRIZ
JAMAL RAFIQUE
DÊNIS P. DE LIMA
Source :
Anais da Academia Brasileira de Ciências, Vol 96, Iss 2 (2024)
Publication Year :
2024
Publisher :
Academia Brasileira de Ciências, 2024.

Abstract

Abstract In pursuit of potential agents to treat Chagas disease and leishmaniasis, we report the design, synthesis, and identification novel naphthoquinone hydrazide-based molecular hybrids. The compounds were subjected to in vitro trypanocide and leishmanicidal activities. N’-(1,4-Dioxo-1,4-dihydronaphthalen-2-yl)-3,5-dimethoxybenzohydrazide (13) showed the best performance against Trypanosoma cruzi (IC50 1.83 µM) and Leishmania amazonensis (IC50 9.65 µM). 4-Bromo-N’-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzohydrazide (16) exhibited leishmanicidal activity (IC50 12.16 µM). Regarding trypanocide activity, compound 13 was low cytotoxic to LLC-MK2 cells (SI = 95.28). Furthermore, through molecular modeling studies, the cysteine proteases cruzain, rhodesain and CPB2.8 were identified as the potential biological targets.

Details

Language :
English
ISSN :
16782690 and 00013765
Volume :
96
Issue :
2
Database :
Directory of Open Access Journals
Journal :
Anais da Academia Brasileira de Ciências
Publication Type :
Academic Journal
Accession number :
edsdoj.0adb625c4550495bb17bb55f60332f9f
Document Type :
article
Full Text :
https://doi.org/10.1590/0001-3765202420230375