Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)

ilustraciones, fotografías color

Autores:: Rodríguez Huerto, Paula Andrea

Tipo de recurso:

Fecha de publicación:: 2022

Institución:: Universidad Nacional de Colombia

Repositorio:: Universidad Nacional de Colombia

Idioma:: spa

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repository_id_str
dc.title.spa.fl_str_mv	Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)
dc.title.translated.eng.fl_str_mv	Alternative synthesis of dibenzazepine derivatives using essential oil of yerba santa (Piper auritum)
title	Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)
spellingShingle	Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum) Plants, Medicinal Plant Extracts Plantas medicinales Extractos vegetales Aceite esencial Piper auritum Safrol Aminosafrol dibenz[b,e]azocina Benzazepina Essential oil Piper auritum Safrole Aminosafrole Dibenzo[b,e]azozine Benzazepine
title_short	Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)
title_full	Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)
title_fullStr	Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)
title_full_unstemmed	Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)
title_sort	Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)
dc.creator.fl_str_mv	Rodríguez Huerto, Paula Andrea
dc.contributor.advisor.none.fl_str_mv	Ochoa Puentes, Cristian Ávila Murillo, Mónica Constanza
dc.contributor.author.none.fl_str_mv	Rodríguez Huerto, Paula Andrea
dc.contributor.researchgroup.spa.fl_str_mv	Síntesis Orgánica Sostenible Grupo de Investigación en Química de Productos Naturales Vegetales Bioactivos (Quipronab)
dc.contributor.cvlac.spa.fl_str_mv	RODRÍGUEZ HUERTO, PAULA ANDREA
dc.subject.decs.eng.fl_str_mv	Plants, Medicinal Plant Extracts
topic	Plants, Medicinal Plant Extracts Plantas medicinales Extractos vegetales Aceite esencial Piper auritum Safrol Aminosafrol dibenz[b,e]azocina Benzazepina Essential oil Piper auritum Safrole Aminosafrole Dibenzo[b,e]azozine Benzazepine
dc.subject.decs.spa.fl_str_mv	Plantas medicinales Extractos vegetales
dc.subject.proposal.spa.fl_str_mv	Aceite esencial Piper auritum Safrol Aminosafrol dibenz[b,e]azocina Benzazepina
dc.subject.proposal.eng.fl_str_mv	Essential oil Piper auritum Safrole Aminosafrole Dibenzo[b,e]azozine Benzazepine
description	ilustraciones, fotografías color
publishDate	2022
dc.date.issued.none.fl_str_mv	2022-10-07
dc.date.accessioned.none.fl_str_mv	2023-04-27T16:00:45Z
dc.date.available.none.fl_str_mv	2023-04-27T16:00:45Z
dc.type.spa.fl_str_mv	Trabajo de grado - Maestría
dc.type.driver.spa.fl_str_mv	info:eu-repo/semantics/masterThesis
dc.type.version.spa.fl_str_mv	info:eu-repo/semantics/acceptedVersion
dc.type.content.spa.fl_str_mv	Text
dc.type.redcol.spa.fl_str_mv	http://purl.org/redcol/resource_type/TM
status_str	acceptedVersion
dc.identifier.uri.none.fl_str_mv	https://repositorio.unal.edu.co/handle/unal/83803
dc.identifier.instname.spa.fl_str_mv	Universidad Nacional de Colombia
dc.identifier.reponame.spa.fl_str_mv	Repositorio Institucional Universidad Nacional de Colombia
dc.identifier.repourl.spa.fl_str_mv	https://repositorio.unal.edu.co/
url	https://repositorio.unal.edu.co/handle/unal/83803 https://repositorio.unal.edu.co/
identifier_str_mv	Universidad Nacional de Colombia Repositorio Institucional Universidad Nacional de Colombia
dc.language.iso.spa.fl_str_mv	spa
language	spa
dc.relation.references.spa.fl_str_mv	Vizcaíno Páez, S., Safrol y Apiol: metabolismo, preparación de derivados y actividad antifúngica contra el hongo fitopatógeno Botryodiplodia theobromae. Escuela de Química 2014. Secretariat, G., Piper auritum kunth. Taxonomy, G. B., Ed. GBIF.org, 2021. (ICN), I. d. C. N. Colecciones Científicas en Línea. http://www.biovirtual.unal.edu.co/es/. Martínez, J. R.; Stashenko, E. E.; Leyva, M. A.; Rios, A. G., Determinación de la composición química y actividad antioxidante in vitro del aceite esencial de Piper auritum kunth (piperaceae) difundida en la costa colombiana. Scientia et technica 2007, 1 (33), 439-442. Pineda, R. M.; Vizcaíno, S. P.; García, C. M.; Gil, J. H.; Durango, D. L., Chemical composition and antifungal activity of Piper auritum kunth and Piper holtonii C. DC. against phytopathogenic fungi. Chilean Journal of Agricultural Research 2012, 72 (4), 507. Leal, S. M.; Pino, N.; Stashenko, E. E.; Martínez, J. R.; Escobar, P., Antiprotozoal activity of essential oils derived from Piper spp. grown in Colombia. Journal of Essential Oil Research 2013, 25 (6), 512-519. Jairo René Martínez, E. E. S., Miguel Antonio Leyva, Alejandro Garcia Rios, Determinación de la composición química y actividad antioxidante in vitro del aceite esencial de Piper auritum kunth (piperaceae) difundida en la costa colombiana. Scientia et technica 2007, 1 (33), 439-442. nations, F. a. a. o. o. t. u., Flavours and fragrances of plant origin Roma, 1995; p. 22. https://www.fao.org/publications/card/es/c/ca4004e4-8bdf-5c46-9c08-8601c91231c1/. Jeurissen, S. M.; Bogaards, J. J.; Awad, H. M.; Boersma, M. G.; Brand, W.; Fiamegos, Y. C.; van Beek, T. A.; Alink, G. M.; Sudhölter, E. J.; Cnubben, N. H., Human cytochrome P450 enzyme specificity for bioactivation of safrole to the proximate carcinogen 1‘-hydroxysafrole. Chemical research in toxicology 2004, 17(9), 1245-1250. Kouznetsov, V. V., Essential Oils as Chemical Reagents in Heterocyclic Synthesis. Natural Product Communications 2019, 14 (1). Li, Y.; Fabiano-Tixier, A.-S.; Chemat, F., Essential oils as reagents in green chemistry. Springer International Publishing: 2014; Vol. 1. Bakkali, F.; Averbeck, S.; Averbeck, D.; Idaomar, M., Biological effects of essential oils–a review. Food chemical toxicology 2008, 46 (2), 446-475. Raut, J. S.; Karuppayil, S. M., A status review on the medicinal properties of essential oils. Industrial crops products 2014, 62, 250-264 Pavela, R., Essential oils for the development of eco-friendly mosquito larvicides: a review. Industrial crops products 2015, 76, 174-187. Dewick, P. M., Medicinal natural products: a biosynthetic approach. John Wiley & Sons: 2002. Yazdani, F.; Mafi, M.; Farhadi, F.; Tabar-Heidar, K.; Aghapoor, K.; Mohsenzadeh, F.; Darabi, H. R., Supercritical CO2 extraction of essential oil from clove bud: Effect of operation conditions on the selective isolation of eugenol and eugenyl acetate. Zeitschrift für Naturforschung B 2005, 60 (11), 1197-1201 Kouznetsov, V. V., Conexión de Biología y Química vía Síntesis Orgánica dirigida a la Diversidad molecular. Revista de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales 2014, 129-141. Kaufman, T. S., The multiple faces of eugenol. A versatile starting material and building block for organic and bio-organic synthesis and a convenient precursor toward bio-based fine chemicals. Journal of the Brazilian chemical Society 2015, 26 (6), 1055-1085. Lima, L. M., Safrole and the versatility of a natural biophore. Rev. Virtual Quim 2015, 7, 495-538 Kumar, S.; Bawa, S.; Gupta, H., Biological activities of quinoline derivatives. Mini reviews in medicinal chemistry 2009, 9 (14), 1648-1654. Khanam, H., Bioactive Benzofuran derivatives: A review. European journal of medicinal chemistry 2015, 97, 483-504 Kouznetsov, V. V.; Bohorquez, A. R. R.; Stashenko, E. E., Three-component imino Diels–Alder reaction with essential oil and seeds of anise: generation of new tetrahydroquinolines. Tetrahedron Letters 2007, 48 (50), 8855-8860. Peñaranda Gómez, A. l.; Rodríguez Bejarano, O.; Kouznetsov, V. V.; Ochoa-Puentes, C., One-Pot Diastereoselective Synthesis of Tetrahydroquinolines from Star Anise Oil in a Choline Chloride/Zinc Chloride Eutectic Mixture. ACS Sustainable Chemistry Engineering 2019, 7 (22), 18630-18639. J Hitce, M. C., C Bourdon, A Vivés,; X Marat, M. D.-C., Flash-metathesis for the coupling of sustainable (poly) hydroxyl β-methylstyrenes from essential oils. Green Chemistry 2015, 17 (7), 3756-3761. Kouznetsov, V. V.; Merchan Arenas, D.; Romero Bohorquez, A., PEG-400 as green reaction medium for Lewis acid-promoted cycloaddition reactions with isoeugenol and anethole. 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The Journal of Organic Chemistry 1972, 37 (2), 208-215 Sasakura, K.; Sugasawa, T., Synthesis of 11‐phenyl‐5,6‐dihydro‐11H‐ dibenz(b,e)azepine derivatives. Chemischer Informationsdienst 1981, 12 (21), no no. Tsvelikhovsky, D.; Buchwald, S. L., Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloro-N-(2-vinyl) aniline: preparation of carbazoles, indoles, dibenzazepines, and acridines. Journal of the American Chemical Society 2010, 132 (40), 14048-14051 Della Ca', N.; Maestri, G.; Malacria, M.; Derat, E.; Catellani, M., Palladium‐ Catalyzed Reaction of Aryl Iodides with ortho‐Bromoanilines and Norbornene/Norbornadiene: Unexpected Formation of Dibenzoazepine Derivatives. Angewandte Chemie International Edition 2011, 50 (51), 12257-12261 Hilt, G.; Galbiati, F.; Harms, K., A modular approach for the synthesis of dibenzoazepine derivatives. Synthesis 2006, 2006 (21), 3575-3584 Palma, A.; Barajas, J. J.; Kouznetsov, V. V.; Stashenko, E.; Bahsas, A., New and Efficient Synthesis of 6,11-Dihydro-11-ethyl-5H-dibenz[b,e]azepine Derivatives Starting from N-Benzylanilines via Amino-Claisen and Friedel Crafts Methodologies. Synlett 2004. León Méndez, G.; Osorio Fortich, M. d. R.; Martínez Useche, S. R., Comparación de dos métodos de extracción del aceite esencial de Citrus sinensis L. Revista Cubana de Farmacia 2015, 49 (4), 0-0 Muñiz, O. D. M.; Hernández, M. V.; Cruz, I. M., Chemical composition and antioxidant activity of the essential oil of Piper auritum kunth related to the type of soil at Veracruz, Mexico. Academic Journal of Science 2016 Chacón, C.; Granados, J. M.; Lau, N. R.; Rivera, S. L.; Valdiviezo, V. M. R.; Miceli, F. A. G., Actividad antifúngica de extractos de hierba santa (Piper auritum) y jarilla (baccharis glutinosa) contra fusarium spp. Agrociencia 2020, 54 (4), 531-538 Cruz, G.; Morales, S.; López, M., Extracción asistida con microondas de aceite esencial de acuyo (Piper auritum) y evaluación de su efecto antifúngico contra Penicillium expansum. Investigación Y Desarrollo En Ciencia Y Tecnología De Alimentos 2016, 1 (1), 173-178. Espinoza Catalán, L.; Madrid Villegas, A.; Taborga Liber, L.; Villena García, J. C. F., Mauricio; Carrasco Altamirano, H., Synthesis of nine safrole derivatives and their antiproliferative activity towards human cancer cells. Journal of the Chilean Chemical Society 2010, 55, 219-222. Behzad Zeynizadeh; Zahmatkesh, K., First and Efficient Method for Reduction of Aliphatic and Aromatic Nitro Compounds with Zinc Borohydride as Pyridine Zinc Tetrahydroborato Complex: A New Stable Ligand‐Metal Borohydride. 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dc.rights.uri.spa.fl_str_mv	http://creativecommons.org/licenses/by-nc-nd/4.0/
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dc.publisher.spa.fl_str_mv	Universidad Nacional de Colombia
dc.publisher.program.spa.fl_str_mv	Bogotá - Ciencias - Maestría en Ciencias - Química
dc.publisher.faculty.spa.fl_str_mv	Facultad de Ciencias
dc.publisher.place.spa.fl_str_mv	Bogotá,Colombia
dc.publisher.branch.spa.fl_str_mv	Universidad Nacional de Colombia - Sede Bogotá
institution	Universidad Nacional de Colombia
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spelling	Atribución-NoComercial-SinDerivadas 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Ochoa Puentes, Cristian42e14d381f1b918cc0c85c77a0ec35c2Ávila Murillo, Mónica Constanzac7e9747034b686246f89d8af2147f989Rodríguez Huerto, Paula Andrea967f5eea23bfd8dc04653a4f82024dc7Síntesis Orgánica SostenibleGrupo de Investigación en Química de Productos Naturales Vegetales Bioactivos (Quipronab)RODRÍGUEZ HUERTO, PAULA ANDREA2023-04-27T16:00:45Z2023-04-27T16:00:45Z2022-10-07https://repositorio.unal.edu.co/handle/unal/83803Universidad Nacional de ColombiaRepositorio Institucional Universidad Nacional de Colombiahttps://repositorio.unal.edu.co/ilustraciones, fotografías colorEl trabajo de investigación descrito en este documento presenta los resultados obtenidos en la búsqueda de precursores sintéticos a partir de fuentes renovables y su posterior transformación química. Para cumplir con los objetivos de esta investigación se plantearon dos etapas donde la primera parte se enfocó hacia la obtención de aceite esencial de hierba santa (Piper auritum) y la segunda etapa consistió en explorar su potencial sintético dirigido hacia la obtención de derivados azepínicos. El aceite esencial de hierba santa, el cual posee un alto contenido de safrol (fenilpropanoide perteneciente a la lista de sustancias ilícitas de estupefacientes y psicoactivas en Colombia, de acuerdo con la resolución número 823 del 2003), se obtuvo por medio de hidrodestilación convencional y asistida por microondas empleando la parte aérea (hojas, tallos e inflorescencias). El aceite con el mayor contenido del fenilpropanoide (4,26 g safrol/100 g de material vegetal) y mejor calidad se obtuvo mediante idrodestilación convencional a partir de las inflorescencias colectadas en Doradal, Antioquia, con un rendimiento de extracción de 5,18 %p/p. Todos los aceites extraídos se analizaron por cromatografía de gases acoplada a espectrometría de masas (GC-MS) encontrando como componentes comunes y mayoritarios el safrol (72,68 – 89,56 %), terpinoleno y -terpineno. Una vez obtenido el aceite esencial, y con el fin de explorar su potencial sintético, se realizó una nitración (61 %) y reducción (64 %) con el fin de obtener la orto-alil anilina derivada del safrol (aminosafrol). Este precursor permitió obtener una serie de N-bencil derivados de aminosafrol con rendimientos entre 66 y 93 % mediante una reacción one-pot de condensación-reducción empleando benzaldehído y sus análogos con sustituyentes 2-metil, 4-metil, 2-metoxi, 3-metoxi, 4-metoxi, 4-dimetilamino, 4-isopropil, 2-bromo y 4-bromo. Estas aminas secundarias se emplearon por una parte para estudiar la ciclación intramolecular tipo Friedel-Crafts lo que permitió obtener un derivado de dibenzazocina con un rendimiento de 40%; por otra parte, la oxidación de una amina secundaria para generar una nitrona y su posterior ciclación intramolecular 1,3-dipolar, la cual generó diez derivados benzazepínicos con rendimientos entre 19 y 48 % para las dos etapas. En conclusión, ambas propuestas (azocinas y benzazepinas) se realizaron mediante 5 y 6 transformaciones sintéticas respectivamente, teniendo como rendimientos globales de reacción 10,4% y un rango entre 5 - 14%. (Texto tomado de la fuente)The research work described in this document presents the results obtained in the search for synthetic precursors from renewable sources and their subsequent chemical transformation. To meet the objectives of this research, two stages were proposed where the first focused on obtaining essential oil from Hierba Santa (Piper auritum) and the second stage consisted of exploring its synthetic potential directed towards obtaining azepine derivatives. The essential oil of Hierba Santa, which has a high content of safrole (phenylpropanoid belonging to the list of illicit narcotic and psychoactive substances in Colombia, following resolution number 823 of 2003), was obtained employing conventional hydrodistillation and microwave-assisted use of the aerial part (leaves, stems, and inflorescences). The oil with the highest content of phenylpropanoid (4.26 g safrole/100 g of plant material) and the best quality was obtained by conventional hydrodistillation from the inflorescences collected in Doradal, Antioquia, with an extraction yield of 5.18 % w/w. All the extracted oils were analyzed by gas chromatography coupled to mass spectrometry (GC-MS), finding safrole (72.68 – 89.56 %), terpinolene, and y-terpinene as common and major components. Once the essential oil was obtained, and to explore its synthetic potential, nitration (61 %) and reduction (64 %) were performed to obtain the ortho-allyl aniline derived from safrole (aminosafrol). This precursor made it possible to obtain a series of N-benzyl aminosafrole derivatives with yields between 66 and 93 % through a one-pot condensation-reduction reaction using benzaldehyde and its analogs with 2-methyl, 4-methyl, 2-methoxy, 3- methoxy, 4-methoxy, 4-dimethylamino, 4-isopropyl, 2-bromo and 4-bromo substituents. These secondary amines were used, on the one hand, to study the intramolecular FriedelCrafts type cyclization, which allowed obtaining one dibenzazocine derivative with yield of 40%. On the other hand, the oxidation of a secondary amine to generate a nitrone and its subsequent intramolecular 1,3-dipolar cyclization, which generated ten benzazepine derivatives with yields between 19 and 48 % for the two steps. In conclusion, both proposals (azocines and benzazepines) were carried out through 5 and 6 synthetic transformations, respectively, with overall reaction yields of 10.4% and a range between 5 - 14%.MaestríaMaestra en QuímicaQuímica Verde y Síntesis Orgánicaxxiv, 123 páginasapplication/pdfspaUniversidad Nacional de ColombiaBogotá - Ciencias - Maestría en Ciencias - QuímicaFacultad de CienciasBogotá,ColombiaUniversidad Nacional de Colombia - Sede BogotáSíntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)Alternative synthesis of dibenzazepine derivatives using essential oil of yerba santa (Piper auritum)Trabajo de grado - Maestríainfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/acceptedVersionTexthttp://purl.org/redcol/resource_type/TMVizcaíno Páez, S., Safrol y Apiol: metabolismo, preparación de derivados y actividad antifúngica contra el hongo fitopatógeno Botryodiplodia theobromae. 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The Journal of Organic Chemistry 1990, 55 (6), 1736-1744Plants, MedicinalPlant ExtractsPlantas medicinalesExtractos vegetalesAceite esencialPiper auritumSafrolAminosafroldibenz[b,e]azocinaBenzazepinaEssential oilPiper auritumSafroleAminosafroleDibenzo[b,e]azozineBenzazepineEstudiantesInvestigadoresMaestrosPúblico generalORIGINAL1032493703.2023.pdf1032493703.2023.pdfTesis de Maestría en Ciencias - Químicaapplication/pdf6461160https://repositorio.unal.edu.co/bitstream/unal/83803/2/1032493703.2023.pdf7ec2b65132a57d932c7860a1a9ffa253MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-85879https://repositorio.unal.edu.co/bitstream/unal/83803/1/license.txteb34b1cf90b7e1103fc9dfd26be24b4aMD51THUMBNAIL1032493703.2023.pdf.jpg1032493703.2023.pdf.jpgGenerated Thumbnailimage/jpeg5202https://repositorio.unal.edu.co/bitstream/unal/83803/3/1032493703.2023.pdf.jpg1bdf667b01de8160600a1bf00ecc6979MD53unal/83803oai:repositorio.unal.edu.co:unal/838032024-08-01 23:09:47.809Repositorio Institucional 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Colombiarepositorio_nal@unal.edu.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Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)

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