Two series of 4-aryl-3-methyl-1,2,3,4-tetrahydroquinoline derivatives were efficiently synthesized according to a two-step synthesis and evaluated as potential antifungal agents. The key step was the formation of the corresponding N-benzyltetrahydroquinolines 5 via a three-component cationic imino D...

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Autores:
Romero Bohórquez, Arnold R.; Laboratorio de Química Orgánica y Biomolecular, Parque Tecnológico Guatiguará, Universidad Industrial de Santander, A.A. 678, Piedecuesta, Colombia.
Kouznetsov, Vladimir V.; Laboratorio de Química Orgánica y Biomolecular, Parque Tecnológico Guatiguará, Universidad Industrial de Santander, A.A. 678, Piedecuesta, Colombia
Zacchino, Susana A.; Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario. Suipacha 531, 2000-Rosario, Argentina
Tipo de recurso:
Article of journal
Fecha de publicación:
2014
Institución:
Pontificia Universidad Javeriana
Repositorio:
Repositorio Universidad Javeriana
Idioma:
eng
OAI Identifier:
oai:repository.javeriana.edu.co:10554/31464
Acceso en línea:
http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8362
http://hdl.handle.net/10554/31464
Palabra clave:
Biología Química
antifungal activity; tetrahydroquinolines; cationic imino Diels-Alder reaction; Lipinski’s rule; propenylbenzenes
Biorganica
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openAccess
License
Atribución-NoComercial-SinDerivadas 4.0 Internacional
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oai_identifier_str oai:repository.javeriana.edu.co:10554/31464
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repository_id_str
dc.title.english.eng.fl_str_mv Synthesis and in vitro Evaluation of Antifungal Properties of Some 4-Aryl-3-Methyl-1,2,3,4-Tetrahydroquinolines Derivatives
dc.creator.fl_str_mv Romero Bohórquez, Arnold R.; Laboratorio de Química Orgánica y Biomolecular, Parque Tecnológico Guatiguará, Universidad Industrial de Santander, A.A. 678, Piedecuesta, Colombia.
Kouznetsov, Vladimir V.; Laboratorio de Química Orgánica y Biomolecular, Parque Tecnológico Guatiguará, Universidad Industrial de Santander, A.A. 678, Piedecuesta, Colombia
Zacchino, Susana A.; Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario. Suipacha 531, 2000-Rosario, Argentina
dc.contributor.author.none.fl_str_mv Romero Bohórquez, Arnold R.; Laboratorio de Química Orgánica y Biomolecular, Parque Tecnológico Guatiguará, Universidad Industrial de Santander, A.A. 678, Piedecuesta, Colombia.
Kouznetsov, Vladimir V.; Laboratorio de Química Orgánica y Biomolecular, Parque Tecnológico Guatiguará, Universidad Industrial de Santander, A.A. 678, Piedecuesta, Colombia
Zacchino, Susana A.; Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario. Suipacha 531, 2000-Rosario, Argentina
dc.contributor.eng.fl_str_mv Universidad Industrial de Santander
dc.subject.eng.fl_str_mv Biología Química
antifungal activity; tetrahydroquinolines; cationic imino Diels-Alder reaction; Lipinski’s rule; propenylbenzenes
Biorganica
topic Biología Química
antifungal activity; tetrahydroquinolines; cationic imino Diels-Alder reaction; Lipinski’s rule; propenylbenzenes
Biorganica
spellingShingle Biología Química
antifungal activity; tetrahydroquinolines; cationic imino Diels-Alder reaction; Lipinski’s rule; propenylbenzenes
Biorganica
description Two series of 4-aryl-3-methyl-1,2,3,4-tetrahydroquinoline derivatives were efficiently synthesized according to a two-step synthesis and evaluated as potential antifungal agents. The key step was the formation of the corresponding N-benzyltetrahydroquinolines 5 via a three-component cationic imino Diels-Alder cycloaddition. The second step was a catalytic debenzylation to obtain the N-unprotected tetrahydroquinolines 6. The products were isolated and purified by column chromatography. Substances were characterized using nuclear magnetic resonance (NMR) mass spectrometry (MS) and infrared spectroscopy (IR). All compounds were tested in vitro against standardized, clinically important fungi, including yeasts, hialohyphomycetes, and dermatophytes. These studies showed that between the tetrahydroquinoline series tested, compounds 6f and 6g showed antifungal activity, specifically against dermatophytes. The compound 6-methoxy-4-(4-hydroxi-3-methoxyphenyl)-3-methyl-1,2,3,4-tetrahydroquinoline 6g exhibited the best in vitro activity (MIC 32-65 μg/mL). The results indicated that the elimination of benzyl group from the N-benzyltetrahydroquinolines derivatives, as well as the introduction of a hydroxyl group in the 4-aryl substituent caused a significant improvement in the antifungal activity. These results were supplemented by the in silico prediction; most of the tetrahydroquinolines evaluated showed high bioavailability, high drugs score and low potential risk.
publishDate 2014
dc.date.created.none.fl_str_mv 2014-10-10
dc.date.accessioned.none.fl_str_mv 2018-02-24T15:59:59Z
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dc.relation.citationissue.eng.fl_str_mv Universitas Scientiarum; Vol 20, No 2 (2015); 177-189
dc.relation.citationissue.spa.fl_str_mv Universitas Scientiarum; Vol 20, No 2 (2015); 177-189
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dc.publisher.eng.fl_str_mv Pontificia Universidad Javeriana
institution Pontificia Universidad Javeriana
repository.name.fl_str_mv Repositorio Institucional - Pontificia Universidad Javeriana
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spelling Atribución-NoComercial-SinDerivadas 4.0 Internacionalinfo:eu-repo/semantics/openAccessinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Universidad Industrial de SantanderRomero Bohórquez, Arnold R.; Laboratorio de Química Orgánica y Biomolecular, Parque Tecnológico Guatiguará, Universidad Industrial de Santander, A.A. 678, Piedecuesta, Colombia.Kouznetsov, Vladimir V.; Laboratorio de Química Orgánica y Biomolecular, Parque Tecnológico Guatiguará, Universidad Industrial de Santander, A.A. 678, Piedecuesta, ColombiaZacchino, Susana A.; Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario. Suipacha 531, 2000-Rosario, Argentina2018-02-24T15:59:59Z2020-04-15T18:10:51Z2018-02-24T15:59:59Z2020-04-15T18:10:51Z2014-10-10http://revistas.javeriana.edu.co/index.php/scientarium/article/view/836210.11144/Javeriana.SC20-2.siea2027-13520122-7483http://hdl.handle.net/10554/31464PDFapplication/pdfengPontificia Universidad Javerianainfo:eu-repo/grantAgreement/EC/FP7/005714http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8362/9924http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2620http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2621http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2622http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2623http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2624http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2625http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2626http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2627http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2628http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2629Universitas Scientiarum; Vol 20, No 2 (2015); 177-189Universitas Scientiarum; Vol 20, No 2 (2015); 177-189Universitas Scientiarum; Vol 20, No 2 (2015); 177-189Biología Químicaantifungal activity; tetrahydroquinolines; cationic imino Diels-Alder reaction; Lipinski’s rule; propenylbenzenesBiorganicanullnullnullhttp://purl.org/coar/version/c_970fb48d4fbd8a85Artículo de revistahttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1info:eu-repo/semantics/articleSynthesis and in vitro Evaluation of Antifungal Properties of Some 4-Aryl-3-Methyl-1,2,3,4-Tetrahydroquinolines DerivativesTwo series of 4-aryl-3-methyl-1,2,3,4-tetrahydroquinoline derivatives were efficiently synthesized according to a two-step synthesis and evaluated as potential antifungal agents. The key step was the formation of the corresponding N-benzyltetrahydroquinolines 5 via a three-component cationic imino Diels-Alder cycloaddition. The second step was a catalytic debenzylation to obtain the N-unprotected tetrahydroquinolines 6. The products were isolated and purified by column chromatography. Substances were characterized using nuclear magnetic resonance (NMR) mass spectrometry (MS) and infrared spectroscopy (IR). All compounds were tested in vitro against standardized, clinically important fungi, including yeasts, hialohyphomycetes, and dermatophytes. These studies showed that between the tetrahydroquinoline series tested, compounds 6f and 6g showed antifungal activity, specifically against dermatophytes. The compound 6-methoxy-4-(4-hydroxi-3-methoxyphenyl)-3-methyl-1,2,3,4-tetrahydroquinoline 6g exhibited the best in vitro activity (MIC 32-65 μg/mL). The results indicated that the elimination of benzyl group from the N-benzyltetrahydroquinolines derivatives, as well as the introduction of a hydroxyl group in the 4-aryl substituent caused a significant improvement in the antifungal activity. These results were supplemented by the in silico prediction; most of the tetrahydroquinolines evaluated showed high bioavailability, high drugs score and low potential risk.10554/31464oai:repository.javeriana.edu.co:10554/314642023-03-28 16:15:47.234Repositorio Institucional - Pontificia Universidad Javerianarepositorio@javeriana.edu.co