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...
- 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
- Rights
- openAccess
- License
- Atribución-NoComercial-SinDerivadas 4.0 Internacional
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|
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 2020-04-15T18:10:51Z |
dc.date.available.none.fl_str_mv |
2018-02-24T15:59:59Z 2020-04-15T18:10:51Z |
dc.type.coar.fl_str_mv |
http://purl.org/coar/resource_type/c_2df8fbb1 |
dc.type.hasversion.none.fl_str_mv |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
dc.type.local.spa.fl_str_mv |
Artículo de revista |
dc.type.coar.none.fl_str_mv |
http://purl.org/coar/resource_type/c_6501 |
dc.type.driver.none.fl_str_mv |
info:eu-repo/semantics/article |
format |
http://purl.org/coar/resource_type/c_6501 |
dc.identifier.none.fl_str_mv |
http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8362 10.11144/Javeriana.SC20-2.siea |
dc.identifier.issn.none.fl_str_mv |
2027-1352 0122-7483 |
dc.identifier.uri.none.fl_str_mv |
http://hdl.handle.net/10554/31464 |
url |
http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8362 http://hdl.handle.net/10554/31464 |
identifier_str_mv |
10.11144/Javeriana.SC20-2.siea 2027-1352 0122-7483 |
dc.language.iso.none.fl_str_mv |
eng |
language |
eng |
dc.relation.uri.none.fl_str_mv |
info:eu-repo/grantAgreement/EC/FP7/005714 http://revistas.javeriana.edu.co/index.php/scientarium/article/view/8362/9924 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2620 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2621 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2622 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2623 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2624 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2625 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2626 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2627 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2628 http://revistas.javeriana.edu.co/index.php/scientarium/article/downloadSuppFile/8362/2629 |
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 |
dc.relation.citationissue.por.fl_str_mv |
Universitas Scientiarum; Vol 20, No 2 (2015); 177-189 |
dc.rights.eng.fl_str_mv |
info:eu-repo/semantics/openAccess |
dc.rights.licence.*.fl_str_mv |
Atribución-NoComercial-SinDerivadas 4.0 Internacional |
dc.rights.accessrights.none.fl_str_mv |
info:eu-repo/semantics/openAccess |
dc.rights.coar.spa.fl_str_mv |
http://purl.org/coar/access_right/c_abf2 |
rights_invalid_str_mv |
Atribución-NoComercial-SinDerivadas 4.0 Internacional http://purl.org/coar/access_right/c_abf2 |
eu_rights_str_mv |
openAccess |
dc.format.spa.fl_str_mv |
PDF |
dc.format.mimetype.spa.fl_str_mv |
application/pdf |
dc.coverage.none.fl_str_mv |
null null null |
dc.publisher.eng.fl_str_mv |
Pontificia Universidad Javeriana |
institution |
Pontificia Universidad Javeriana |
repository.name.fl_str_mv |
Repositorio Institucional - Pontificia Universidad Javeriana |
repository.mail.fl_str_mv |
repositorio@javeriana.edu.co |
_version_ |
1811671119738961920 |
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 |