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

IF 2.5 4区工程技术 Q3 CHEMISTRY, ANALYTICAL Separations Pub Date : 2023-09-26 DOI:10.3390/separations10100524

Grover Castañeta, Rodrigo Villagomez, Efrain Salamanca, Pamela Canaviri-Paz, José A. Bravo, José L. Vila, Daniela Bárcenas-Pérez, José Cheel, Beatriz Sepúlveda, Alberto Giménez, Carlos Areche

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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, 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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地衣中部分酚类成分的微波辅助半合成及杀利什曼尼菌活性研究

利什曼病被认为是世界上最不受治疗的热带病之一。在本研究中，我们研究了各种分离地衣物质的体外杀鼠活性和细胞毒性，包括阿特拉霉素(1)、usnic酸(2)、gyrophoric酸(3)、salazinic酸(4)、galbinic酸(5)和parietin(6)，以及一些半合成的usnic酸(7,8,9)和atranorin(10,11,12,13)的亚胺衍生物。利用微波加热这一高效环保的能源，研究了亚胺与肼和几种胺的缩合反应。最有趣的结果是化合物2，它具有很高的利什曼尼杀灭活性，但也有很高的细胞毒性。这种细胞毒性在其衍生物中得到缓解，9具有更好的选择性和高抗利什曼活性。这一结果可能表明，与两个环己胺基团缩合得到的usic酸衍生物(9)是一个很有希望发现新的半合成抗寄生虫药物的先导化合物。

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来源期刊

Separations Chemistry-Analytical Chemistry

CiteScore

3.00

自引率

15.40%

发文量

342

审稿时长

12 weeks

期刊介绍： Separations (formerly Chromatography, ISSN 2227-9075, CODEN: CHROBV) provides an advanced forum for separation and purification science and technology in all areas of chemical, biological and physical science. It publishes reviews, regular research papers and communications. Our aim is to encourage scientists to publish their experimental and theoretical results in as much detail as possible. There is no restriction on the length of the papers. The full experimental details must be provided so that the results can be reproduced. There are, in addition, unique features of this journal: Manuscripts regarding research proposals and research ideas will be particularly welcomed. Electronic files and software regarding the full details of the calculation and experimental procedure, if unable to be published in a normal way, can be deposited as supplementary material. Manuscripts concerning summaries and surveys on research cooperation and projects (that are funded by national governments) to give information for a broad field of users. The scope of the journal includes but is not limited to: Theory and methodology (theory of separation methods, sample preparation, instrumental and column developments, new separation methodologies, etc.) Equipment and techniques, novel hyphenated analytical solutions (significantly extended by their combination with spectroscopic methods and in particular, mass spectrometry) Novel analysis approaches and applications to solve analytical challenges which utilize chromatographic separations as a key step in the overall solution Computational modelling of separations for the purpose of fundamental understanding and/or chromatographic optimization