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

0579672 - MBÚ 2024 RIV CH eng J - Journal Article
Castaneta, G. - Villagomez, R. - Salamanca, E. - Canaviri-Paz, P. - Bravo, Jose A. - Vila, Jose L. - Bárcenas-Pérez, Daniela - Cheel Horna, José - Sepúlveda, B. - Gimenez, A. - Areche, C.
Microwave-Assisted Semisynthesis and Leishmanicidal Activity of Some Phenolic Constituents from Lichens.
Separations. Roč. 10, č. 10 (2023), č. článku 524. E-ISSN 2297-8739
Institutional support: RVO:61388971
Keywords : usnic acid * chemical-modification * alkaloid extract * (+)-usnic acid * atranorin derivatives * cytotoxicity * green chemistry * imine * leishmania * pyrazoline * usnic acid derivatives
OECD category: Analytical chemistry
Impact factor: 2.6, year: 2022
Method of publishing: Open access
https://www.mdpi.com/2297-8739/10/10/524

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.
Permanent Link: https://hdl.handle.net/11104/0348488