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Microwave-Assisted Semisynthesis and Leishmanicidal Activity of Some Phenolic Constituents from Lichens

Castañeta, Grover ; Villagomez, Rodrigo ; Salamanca, Efrain ; Canaviri-Paz, Pamela LU ; Bravo, José A. ; Vila, José L. ; Bárcenas-Pérez, Daniela ; Cheel, José ; Sepúlveda, Beatriz and Giménez, Alberto , et al. (2023) In separations 10(10).
Abstract

Leishmaniasis is considered one of the most untreated tropical diseases in the world. In this study, we investigated the in vitro leishmanicidal activity and cytotoxicity of various isolated lichen substances, including atranorin (1), usnic acid (2), gyrophoric acid (3), salazinic acid (4), galbinic acid (5), and parietin (6), and some semi-synthetic imine derivatives of usnic acid (7, 8, 9) and atranorin (10, 11, 12, 13). Imine condensation reactions with hydrazine and several amines were assisted by microwave heating, an efficient and eco-friendly energy source. The most interesting result was obtained for compound 2, which has high leishmanicidal activity but also high cytotoxicity. This cytotoxicity was mitigated in its derivative,... (More)

Leishmaniasis is considered one of the most untreated tropical diseases in the world. In this study, we investigated the in vitro leishmanicidal activity and cytotoxicity of various isolated lichen substances, including atranorin (1), usnic acid (2), gyrophoric acid (3), salazinic acid (4), galbinic acid (5), and parietin (6), and some semi-synthetic imine derivatives of usnic acid (7, 8, 9) and atranorin (10, 11, 12, 13). Imine condensation reactions with hydrazine and several amines were assisted by microwave heating, an efficient and eco-friendly energy source. The most interesting result was obtained for compound 2, which has high leishmanicidal activity but also high cytotoxicity. This cytotoxicity was mitigated in its derivative, 9, with better selectivity and high antileishmanic activity. This result may indicate that the usnic acid derivative (9) obtained using condensation with two cyclohexylamine groups is a promising lead compound for the discovery of new semisynthetic antiparasitic drugs.

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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
atranorin derivatives, cytotoxicity, green chemistry, imine, leishmania, pyrazoline, usnic acid derivatives
in
separations
volume
10
issue
10
article number
524
publisher
MDPI AG
external identifiers
  • scopus:85175477459
ISSN
2297-8739
DOI
10.3390/separations10100524
language
English
LU publication?
yes
id
909d83b2-6d2e-4eda-b30b-7da55f7656a4
date added to LUP
2023-11-24 11:31:33
date last changed
2023-11-24 11:33:18
@article{909d83b2-6d2e-4eda-b30b-7da55f7656a4,
  abstract     = {{<p>Leishmaniasis is considered one of the most untreated tropical diseases in the world. In this study, we investigated the in vitro leishmanicidal activity and cytotoxicity of various isolated lichen substances, including atranorin (1), usnic acid (2), gyrophoric acid (3), salazinic acid (4), galbinic acid (5), and parietin (6), and some semi-synthetic imine derivatives of usnic acid (7, 8, 9) and atranorin (10, 11, 12, 13). Imine condensation reactions with hydrazine and several amines were assisted by microwave heating, an efficient and eco-friendly energy source. The most interesting result was obtained for compound 2, which has high leishmanicidal activity but also high cytotoxicity. This cytotoxicity was mitigated in its derivative, 9, with better selectivity and high antileishmanic activity. This result may indicate that the usnic acid derivative (9) obtained using condensation with two cyclohexylamine groups is a promising lead compound for the discovery of new semisynthetic antiparasitic drugs.</p>}},
  author       = {{Castañeta, Grover and Villagomez, Rodrigo and Salamanca, Efrain and Canaviri-Paz, Pamela and Bravo, José A. and Vila, José L. and Bárcenas-Pérez, Daniela and Cheel, José and Sepúlveda, Beatriz and Giménez, Alberto and Areche, Carlos}},
  issn         = {{2297-8739}},
  keywords     = {{atranorin derivatives; cytotoxicity; green chemistry; imine; leishmania; pyrazoline; usnic acid derivatives}},
  language     = {{eng}},
  number       = {{10}},
  publisher    = {{MDPI AG}},
  series       = {{separations}},
  title        = {{Microwave-Assisted Semisynthesis and Leishmanicidal Activity of Some Phenolic Constituents from Lichens}},
  url          = {{http://dx.doi.org/10.3390/separations10100524}},
  doi          = {{10.3390/separations10100524}},
  volume       = {{10}},
  year         = {{2023}},
}