Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol
Leishmaniasis represents a series of severe neglected tropical diseases caused by protozoa of the genus Leishmania and is widely distributed around the world. Here, we present the syntheses of Morita-Baylis-Hillman adducts (MBHAs) prepared from eugenol, thymol and carvacrol, and their bioevaluation...
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| Format: | Article |
| Language: | English |
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MDPI AG
2016-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/11/1483 |
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| author | Francisco José Seixas Xavier Klinger Antonio da Franca Rodrigues Ramon Guerra de Oliveira Claudio Gabriel Lima Junior Juliana da Câmara Rocha Tatjana Souza Lima Keesen Marcia Rosa de Oliveira Fábio Pedrosa Lins Silva Mário Luiz Araújo de Almeida Vasconcellos |
| author_facet | Francisco José Seixas Xavier Klinger Antonio da Franca Rodrigues Ramon Guerra de Oliveira Claudio Gabriel Lima Junior Juliana da Câmara Rocha Tatjana Souza Lima Keesen Marcia Rosa de Oliveira Fábio Pedrosa Lins Silva Mário Luiz Araújo de Almeida Vasconcellos |
| author_sort | Francisco José Seixas Xavier |
| collection | DOAJ |
| description | Leishmaniasis represents a series of severe neglected tropical diseases caused by protozoa of the genus Leishmania and is widely distributed around the world. Here, we present the syntheses of Morita-Baylis-Hillman adducts (MBHAs) prepared from eugenol, thymol and carvacrol, and their bioevaluation against promastigotes of Leishmania amazonensis. The new MBHAs are prepared in two steps from essential oils in moderate to good yields and present IC50 values in the range of 22.30–4.71 μM. Moreover, the selectivity index to the most potent compound is very high (SIrb > 84.92), far better than that of Glucantime® (SIrb 1.39) and amphotericin B (SIrb = 22.34). Conformational analysis were carried out at the M062X//6-31+G(d,p) level of theory to corroborate a hypothesis about the nitroaromatic bioreduction mechanism. |
| first_indexed | 2024-12-13T04:14:37Z |
| format | Article |
| id | doaj.art-d42a07c9888f475dbefc599e861c0458 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T04:14:37Z |
| publishDate | 2016-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d42a07c9888f475dbefc599e861c04582022-12-21T23:59:55ZengMDPI AGMolecules1420-30492016-11-012111148310.3390/molecules21111483molecules21111483Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and CarvacrolFrancisco José Seixas Xavier0Klinger Antonio da Franca Rodrigues1Ramon Guerra de Oliveira2Claudio Gabriel Lima Junior3Juliana da Câmara Rocha4Tatjana Souza Lima Keesen5Marcia Rosa de Oliveira6Fábio Pedrosa Lins Silva7Mário Luiz Araújo de Almeida Vasconcellos8Laboratório de Síntese Orgânica Medicinal da Paraíba (LASOM-PB), Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, Paraíba CEP 58059-900, BrazilPrograma de Pós-graduação em Biologia Molecular and Departamento de Biologia Molecular, Centro de Ciências Exatas and da Natureza, Universidade Federal da Paraíba, João Pessoa, Paraíba CEP 58059-900, BrazilLaboratório de Síntese Orgânica Medicinal da Paraíba (LASOM-PB), Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, Paraíba CEP 58059-900, BrazilLaboratório de Síntese Orgânica Medicinal da Paraíba (LASOM-PB), Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, Paraíba CEP 58059-900, BrazilDepartamento de Biotecnologia, Universidade Federal da Paraíba, Campus I, João Pessoa, Paraíba CEP 58059-900, BrazilDepartamento de Biotecnologia, Universidade Federal da Paraíba, Campus I, João Pessoa, Paraíba CEP 58059-900, BrazilPrograma de Pós-graduação em Biologia Molecular and Departamento de Biologia Molecular, Centro de Ciências Exatas and da Natureza, Universidade Federal da Paraíba, João Pessoa, Paraíba CEP 58059-900, BrazilLaboratório de Síntese Orgânica Medicinal da Paraíba (LASOM-PB), Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, Paraíba CEP 58059-900, BrazilLaboratório de Síntese Orgânica Medicinal da Paraíba (LASOM-PB), Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, Paraíba CEP 58059-900, BrazilLeishmaniasis represents a series of severe neglected tropical diseases caused by protozoa of the genus Leishmania and is widely distributed around the world. Here, we present the syntheses of Morita-Baylis-Hillman adducts (MBHAs) prepared from eugenol, thymol and carvacrol, and their bioevaluation against promastigotes of Leishmania amazonensis. The new MBHAs are prepared in two steps from essential oils in moderate to good yields and present IC50 values in the range of 22.30–4.71 μM. Moreover, the selectivity index to the most potent compound is very high (SIrb > 84.92), far better than that of Glucantime® (SIrb 1.39) and amphotericin B (SIrb = 22.34). Conformational analysis were carried out at the M062X//6-31+G(d,p) level of theory to corroborate a hypothesis about the nitroaromatic bioreduction mechanism.http://www.mdpi.com/1420-3049/21/11/1483Morita-Baylis-Hillman adductsLeishmania amazonensiseugenolthymolcarvacrol |
| spellingShingle | Francisco José Seixas Xavier Klinger Antonio da Franca Rodrigues Ramon Guerra de Oliveira Claudio Gabriel Lima Junior Juliana da Câmara Rocha Tatjana Souza Lima Keesen Marcia Rosa de Oliveira Fábio Pedrosa Lins Silva Mário Luiz Araújo de Almeida Vasconcellos Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol Molecules Morita-Baylis-Hillman adducts Leishmania amazonensis eugenol thymol carvacrol |
| title | Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol |
| title_full | Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol |
| title_fullStr | Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol |
| title_full_unstemmed | Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol |
| title_short | Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol |
| title_sort | synthesis and in vitro anti leishmania amazonensis biological screening of morita baylis hillman adducts prepared from eugenol thymol and carvacrol |
| topic | Morita-Baylis-Hillman adducts Leishmania amazonensis eugenol thymol carvacrol |
| url | http://www.mdpi.com/1420-3049/21/11/1483 |
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