TY - JOUR
T1 - Microwave-Assisted Semisynthesis and Leishmanicidal Activity of Some Phenolic Constituents from Lichens
AU - Castañeta, Grover
AU - Villagomez, Rodrigo
AU - Salamanca, Efrain
AU - Canaviri-Paz, Pamela
AU - Bravo, José A.
AU - Vila, José L.
AU - Bárcenas-Pérez, Daniela
AU - Cheel, José
AU - Sepúlveda, Beatriz
AU - Giménez, Alberto
AU - Areche, Carlos
N1 - Publisher Copyright:
© 2023 by the authors.
PY - 2023/10
Y1 - 2023/10
N2 - 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.
AB - 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.
KW - atranorin derivatives
KW - cytotoxicity
KW - green chemistry
KW - imine
KW - leishmania
KW - pyrazoline
KW - usnic acid derivatives
UR - http://www.scopus.com/inward/record.url?scp=85175477459&partnerID=8YFLogxK
U2 - 10.3390/separations10100524
DO - 10.3390/separations10100524
M3 - Artículo
AN - SCOPUS:85175477459
SN - 2297-8739
VL - 10
JO - Separations
JF - Separations
IS - 10
M1 - 524
ER -
