Abstract:
A series of hydroxyalkyl and acyloxyalkyl derivatives of 2- and 3-hydroxypyridine was synthesized and their biological activity was evaluated as growth inhibitors of protozoan Leishmania mexicana. Thirty novel compounds were obtained through a chemoenzymatic methodology in two reaction steps. The influence of various reaction parameters in the enzymatic step, such as enzyme source, acylating agent/substrate ratio, enzyme/substrate ratio, solvent and temperature, was studied. Some of the evaluated compounds showed a remarkable activity as Leishmania mexicana growth inhibitors, obtaining the best results with the acetylated derivatives. The advantages showed by the enzymatic methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to prepare these derivatives of substituted pyridines with application as potential antiparasitic agents. © 2012 Elsevier Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Chemoenzymatic synthesis and biological evaluation of 2- and 3-hydroxypyridine derivatives against Leishmania mexicana |
Autor: | García Liñares, G.; Parraud, G.; Labriola, C.; Baldessari, A. |
Filiación: | Departamento de Química Orgánica y UMYMFOR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, piso 3, C1428EGA Buenos Aires, Argentina Instituto de Investigaciones Bioquímicas, Av. Patricias Argentinas, 435C1405BWE Buenos Aires, Argentina
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Palabras clave: | Hydroxypyridine derivatives; Leishmaniasis; Lipase-catalyzed; Synthesis; 10 (pyridin 2 yloxy) decan 1 ol; 10 (pyridin 3 yloxy) decan 1 ol; 10 (pyridin 3 yloxy) decyl acetate; 11 (pyridin 2 yloxy) undecan 1 ol; 11 (pyridin 3 yloxy) undecan 1 ol; 11 (pyridin 3 yloxy) undecyl acetate; 12 (pyridin 2 yloxy) dodecan 1 ol; 12 (pyridin 3 yloxy) dodecan 1 ol; 12 (pyridin 3 yloxy) dodecyl acetate; 2 hydroxypyridine derivative; 3 hydroxypyridine derivative; 6 (pyridin 2 yloxy) hexan 1 ol; 6 (pyridin 2 yloxy) hexyl acetate; 6 (pyridin 3 yloxy) hexan 1 ol; 6 (pyridin 3 yloxy) hexyl acetate; 7 (pyridin 2 yloxy) heptan 1 ol; 7 (pyridin 2 yloxy) heptyl acetate; 7 (pyridin 3 yloxy) heptan 1 ol; 7 (pyridin 3 yloxy) heptyl acetate; 8 (pyridin 2 yloxy) octan 1 ol; 8 (pyridin 2 yloxy) octyl acetate; 8 (pyridin 3 yloxy) octan 1 ol; 8 (pyridin 3 yloxy) octyl acetate; 9 (pyridin 2 yloxy) nonan 1 ol; 9 (pyridin 2 yloxy) nonyl acetate; 9 (pyridin 3 yloxy) nonan 1 ol; 9 (pyridin 3 yloxy) nonyl acetate; antiparasitic agent; pyridine derivative; unclassified drug; unindexed drug; article; biocatalysis; controlled study; drug screening; drug structure; drug synthesis; enzyme chemistry; enzyme substrate; Leishmania mexicana; nonhuman; temperature; Antiprotozoal Agents; Biocatalysis; Dose-Response Relationship, Drug; Drug Evaluation, Preclinical; Leishmania mexicana; Lipase; Molecular Structure; Parasitic Sensitivity Tests; Pyridines; Structure-Activity Relationship; Leishmania mexicana; Protozoa |
Año: | 2012
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Volumen: | 20
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Número: | 15
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Página de inicio: | 4614
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Página de fin: | 4624
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DOI: |
http://dx.doi.org/10.1016/j.bmc.2012.06.028 |
Título revista: | Bioorganic and Medicinal Chemistry
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Título revista abreviado: | Bioorg. Med. Chem.
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ISSN: | 09680896
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CODEN: | BMECE
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CAS: | Antiprotozoal Agents; Lipase, 3.1.1.3; Pyridines; hydroxypyridines
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v20_n15_p4614_GarciaLinares |
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Citas:
---------- APA ----------
García Liñares, G., Parraud, G., Labriola, C. & Baldessari, A.
(2012)
. Chemoenzymatic synthesis and biological evaluation of 2- and 3-hydroxypyridine derivatives against Leishmania mexicana. Bioorganic and Medicinal Chemistry, 20(15), 4614-4624.
http://dx.doi.org/10.1016/j.bmc.2012.06.028---------- CHICAGO ----------
García Liñares, G., Parraud, G., Labriola, C., Baldessari, A.
"Chemoenzymatic synthesis and biological evaluation of 2- and 3-hydroxypyridine derivatives against Leishmania mexicana"
. Bioorganic and Medicinal Chemistry 20, no. 15
(2012) : 4614-4624.
http://dx.doi.org/10.1016/j.bmc.2012.06.028---------- MLA ----------
García Liñares, G., Parraud, G., Labriola, C., Baldessari, A.
"Chemoenzymatic synthesis and biological evaluation of 2- and 3-hydroxypyridine derivatives against Leishmania mexicana"
. Bioorganic and Medicinal Chemistry, vol. 20, no. 15, 2012, pp. 4614-4624.
http://dx.doi.org/10.1016/j.bmc.2012.06.028---------- VANCOUVER ----------
García Liñares, G., Parraud, G., Labriola, C., Baldessari, A. Chemoenzymatic synthesis and biological evaluation of 2- and 3-hydroxypyridine derivatives against Leishmania mexicana. Bioorg. Med. Chem. 2012;20(15):4614-4624.
http://dx.doi.org/10.1016/j.bmc.2012.06.028