{"id":{"repo_id":"brazil-uff","oai_identifier":"oai:app.uff.br:1/18070"},"canonical_url":"https://search.dev.ndltd.org/etd/brazil-uff/oai:app.uff.br:1/18070","repository":{"repo_id":"brazil-uff","name":"Brazil UFF","base_url":"https://app.uff.br/oai/request"},"display":{"title":"SÍNTESE DE NOVOS DERIVADOS DE LAPACHONAS E NOR-LAPACHONAS: VEREDAS À ATIVIDADE FARMACOLÓGICA","abstract":"In the present work the reactivity of orto-furan-naphthoquinones, para-furannaphthoquinones and para-piran-naphthoquinones was studied, in order to produce new pharmacological prototype compounds. Eighteen novel naphthoquinones were prepared. The orto-furan-naphthoquinones 3-(2,5-dimethyl-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (64), 3-(4-fluoro-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (65), 3-(3-chloro-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (66), 3-(3-bromo-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (67), 2,2-dimethyl-3-(3-nitro-phenylamino)-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (68) and 3-(3-fluoro-phenylamino)-2,2-dimethyl- 2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (69) were obtained, starting from the key intermediate 3-bromo-nor-β-lapachone (37). A great number of possibilities was opened with the obtaining the naphthoquinones 3-azido-2,2-dimethyl-2,3-dihydro-naphtho[1,2- b]furan-4,5-dione (79), 4-azido-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10- dione (86) and 3-azido-2,2-dimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9-dione (93). The orto-furan-naphthoquinones 3-[4-(1-hydroxy-cyclohexyl)-[1,2,3]triazol-1-yl]-2,2- dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (80), 3-[4-(1-hydroxy-1-methylethyl)-[ 1,2,3]triazol-1-yl]-2,2-dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (81), 2,2-dimethyl-3-(4-phenyl-[1,2,3]triazol-1-yl)-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (82), 3-(4-hydroxymethyl-[1,2,3]triazol-1-yl)-2,2-dimethyl-2,3-dihydro-naphtho[1,2- b]furan-4,5-dione (83), 2,2-dimethyl-3-[4-(tetrahydro-pyran-2-yloxymethyl)-[1,2,3]triazol- 1-yl]-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (84) and 3-(4-cyclohex-1-enyl- [1,2,3]triazol-1-yl)-2,2-dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (85). The compounds para-furan-naphthoquinones and para-piran-naphthoquinones 2,2- dimethyl-3-phenylamino-2,3-dihydro-naphtho[2,3-b]furan-4,9-dione (70) and 2,2- dimethyl-4-phenylamino-3,4-dihydro-2H-benzo[g]chromene-5,10-dione (72) were obtained in good yields by a similar methodology to that one used for the synthesis of ortonaphthoquinones. The epoxide of the 2,2-dimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9- dione (28) was obtained in good yield. The results of the anti-cancer activities of naphthoquinones 64, 65, 66, 67, 68, 70, 72, 76, 79, 80, 81, 82 e 83 over human tumor cell lines indicate the potential of these compounds for the treatment of cancer and their anti-trypanocidal activities for the compounds 64, 65, 66, 67, 68, 70, 72, 76, 79, 80, 81, 82, 83 e 85 also indicate for these compounds important pharmacological potencial.","abstract_html":"In the present work the reactivity of orto-furan-naphthoquinones, para-furannaphthoquinones and para-piran-naphthoquinones was studied, in order to produce new pharmacological prototype compounds. Eighteen novel naphthoquinones were prepared. The orto-furan-naphthoquinones 3-(2,5-dimethyl-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (64), 3-(4-fluoro-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (65), 3-(3-chloro-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (66), 3-(3-bromo-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (67), 2,2-dimethyl-3-(3-nitro-phenylamino)-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (68) and 3-(3-fluoro-phenylamino)-2,2-dimethyl- 2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (69) were obtained, starting from the key intermediate 3-bromo-nor-β-lapachone (37). A great number of possibilities was opened with the obtaining the naphthoquinones 3-azido-2,2-dimethyl-2,3-dihydro-naphtho[1,2- b]furan-4,5-dione (79), 4-azido-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10- dione (86) and 3-azido-2,2-dimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9-dione (93). The orto-furan-naphthoquinones 3-[4-(1-hydroxy-cyclohexyl)-[1,2,3]triazol-1-yl]-2,2- dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (80), 3-[4-(1-hydroxy-1-methylethyl)-[ 1,2,3]triazol-1-yl]-2,2-dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (81), 2,2-dimethyl-3-(4-phenyl-[1,2,3]triazol-1-yl)-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (82), 3-(4-hydroxymethyl-[1,2,3]triazol-1-yl)-2,2-dimethyl-2,3-dihydro-naphtho[1,2- b]furan-4,5-dione (83), 2,2-dimethyl-3-[4-(tetrahydro-pyran-2-yloxymethyl)-[1,2,3]triazol- 1-yl]-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (84) and 3-(4-cyclohex-1-enyl- [1,2,3]triazol-1-yl)-2,2-dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (85). The compounds para-furan-naphthoquinones and para-piran-naphthoquinones 2,2- dimethyl-3-phenylamino-2,3-dihydro-naphtho[2,3-b]furan-4,9-dione (70) and 2,2- dimethyl-4-phenylamino-3,4-dihydro-2H-benzo[g]chromene-5,10-dione (72) were obtained in good yields by a similar methodology to that one used for the synthesis of ortonaphthoquinones. The epoxide of the 2,2-dimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9- dione (28) was obtained in good yield. The results of the anti-cancer activities of naphthoquinones 64, 65, 66, 67, 68, 70, 72, 76, 79, 80, 81, 82 e 83 over human tumor cell lines indicate the potential of these compounds for the treatment of cancer and their anti-trypanocidal activities for the compounds 64, 65, 66, 67, 68, 70, 72, 76, 79, 80, 81, 82, 83 e 85 also indicate for these compounds important pharmacological potencial.","abstract_has_math":false,"creators":["Silva Júnior, Eufrânio Nunes da"],"institution":"Programa de Pós-graduação em Química Orgânica","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2007,"date_issued":"2007-06-29","date_published":"2007-06-29","updated_at":"2026-07-27T19:00:28Z","subjects":["Lapachol","Quinona","Triazol","Composto heterocíclico","Naftoquinona Derivados","Lapachona.","Quinone","Triazole"],"languages":["por"],"rights":["Acesso Embargado"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://app.uff.br/riuff/handle/1/18070","outbound_label":"Repository record","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Silva Júnior, Eufrânio Nunes da"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2021-03-10T20:43:31Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2008-11-07","2021-03-10T20:43:31Z"]},{"key":"dc:date.issued","label":"Date","values":["2007-06-29"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Química Orgânica"]},{"key":"dc:type","label":"Dc Type","values":["Dissertação"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Lapachol","Quinona","Triazol","Composto heterocíclico","Naftoquinona Derivados","Lapachona.","Quinone","Triazole"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["por"]},{"key":"dc:rights","label":"Dc Rights","values":["Acesso Embargado"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://app.uff.br/riuff/handle/1/18070"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["In the present work the reactivity of orto-furan-naphthoquinones, para-furannaphthoquinones and para-piran-naphthoquinones was studied, in order to produce new pharmacological prototype compounds. Eighteen novel naphthoquinones were prepared. The orto-furan-naphthoquinones 3-(2,5-dimethyl-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (64), 3-(4-fluoro-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (65), 3-(3-chloro-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (66), 3-(3-bromo-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (67), 2,2-dimethyl-3-(3-nitro-phenylamino)-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (68) and 3-(3-fluoro-phenylamino)-2,2-dimethyl- 2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (69) were obtained, starting from the key intermediate 3-bromo-nor-β-lapachone (37). A great number of possibilities was opened with the obtaining the naphthoquinones 3-azido-2,2-dimethyl-2,3-dihydro-naphtho[1,2- b]furan-4,5-dione (79), 4-azido-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10- dione (86) and 3-azido-2,2-dimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9-dione (93). The orto-furan-naphthoquinones 3-[4-(1-hydroxy-cyclohexyl)-[1,2,3]triazol-1-yl]-2,2- dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (80), 3-[4-(1-hydroxy-1-methylethyl)-[ 1,2,3]triazol-1-yl]-2,2-dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (81), 2,2-dimethyl-3-(4-phenyl-[1,2,3]triazol-1-yl)-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (82), 3-(4-hydroxymethyl-[1,2,3]triazol-1-yl)-2,2-dimethyl-2,3-dihydro-naphtho[1,2- b]furan-4,5-dione (83), 2,2-dimethyl-3-[4-(tetrahydro-pyran-2-yloxymethyl)-[1,2,3]triazol- 1-yl]-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (84) and 3-(4-cyclohex-1-enyl- [1,2,3]triazol-1-yl)-2,2-dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (85). The compounds para-furan-naphthoquinones and para-piran-naphthoquinones 2,2- dimethyl-3-phenylamino-2,3-dihydro-naphtho[2,3-b]furan-4,9-dione (70) and 2,2- dimethyl-4-phenylamino-3,4-dihydro-2H-benzo[g]chromene-5,10-dione (72) were obtained in good yields by a similar methodology to that one used for the synthesis of ortonaphthoquinones. The epoxide of the 2,2-dimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9- dione (28) was obtained in good yield. The results of the anti-cancer activities of naphthoquinones 64, 65, 66, 67, 68, 70, 72, 76, 79, 80, 81, 82 e 83 over human tumor cell lines indicate the potential of these compounds for the treatment of cancer and their anti-trypanocidal activities for the compounds 64, 65, 66, 67, 68, 70, 72, 76, 79, 80, 81, 82, 83 e 85 also indicate for these compounds important pharmacological potencial."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["SÍNTESE DE NOVOS DERIVADOS DE LAPACHONAS E NOR-LAPACHONAS: VEREDAS À ATIVIDADE FARMACOLÓGICA"]}]}],"canonical_facts":{"dc:creator":["Silva Júnior, Eufrânio Nunes da"],"dc:date.accessioned":["2021-03-10T20:43:31Z"],"dc:date.available":["2008-11-07","2021-03-10T20:43:31Z"],"dc:date.issued":["2007-06-29"],"dc:description.abstract":["In the present work the reactivity of orto-furan-naphthoquinones, para-furannaphthoquinones and para-piran-naphthoquinones was studied, in order to produce new pharmacological prototype compounds. Eighteen novel naphthoquinones were prepared. The orto-furan-naphthoquinones 3-(2,5-dimethyl-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (64), 3-(4-fluoro-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (65), 3-(3-chloro-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (66), 3-(3-bromo-phenylamino)-2,2-dimethyl-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (67), 2,2-dimethyl-3-(3-nitro-phenylamino)-2,3- dihydro-naphtho[1,2-b]furan-4,5-dione (68) and 3-(3-fluoro-phenylamino)-2,2-dimethyl- 2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (69) were obtained, starting from the key intermediate 3-bromo-nor-β-lapachone (37). A great number of possibilities was opened with the obtaining the naphthoquinones 3-azido-2,2-dimethyl-2,3-dihydro-naphtho[1,2- b]furan-4,5-dione (79), 4-azido-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10- dione (86) and 3-azido-2,2-dimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9-dione (93). The orto-furan-naphthoquinones 3-[4-(1-hydroxy-cyclohexyl)-[1,2,3]triazol-1-yl]-2,2- dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (80), 3-[4-(1-hydroxy-1-methylethyl)-[ 1,2,3]triazol-1-yl]-2,2-dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (81), 2,2-dimethyl-3-(4-phenyl-[1,2,3]triazol-1-yl)-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (82), 3-(4-hydroxymethyl-[1,2,3]triazol-1-yl)-2,2-dimethyl-2,3-dihydro-naphtho[1,2- b]furan-4,5-dione (83), 2,2-dimethyl-3-[4-(tetrahydro-pyran-2-yloxymethyl)-[1,2,3]triazol- 1-yl]-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (84) and 3-(4-cyclohex-1-enyl- [1,2,3]triazol-1-yl)-2,2-dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione (85). The compounds para-furan-naphthoquinones and para-piran-naphthoquinones 2,2- dimethyl-3-phenylamino-2,3-dihydro-naphtho[2,3-b]furan-4,9-dione (70) and 2,2- dimethyl-4-phenylamino-3,4-dihydro-2H-benzo[g]chromene-5,10-dione (72) were obtained in good yields by a similar methodology to that one used for the synthesis of ortonaphthoquinones. The epoxide of the 2,2-dimethyl-2,3-dihydro-naphtho[2,3-b]furan-4,9- dione (28) was obtained in good yield. The results of the anti-cancer activities of naphthoquinones 64, 65, 66, 67, 68, 70, 72, 76, 79, 80, 81, 82 e 83 over human tumor cell lines indicate the potential of these compounds for the treatment of cancer and their anti-trypanocidal activities for the compounds 64, 65, 66, 67, 68, 70, 72, 76, 79, 80, 81, 82, 83 e 85 also indicate for these compounds important pharmacological potencial."],"dc:format":["application/pdf"],"dc:identifier.uri":["https://app.uff.br/riuff/handle/1/18070"],"dc:language":["por"],"dc:publisher.department":["Química Orgânica"],"dc:rights":["Acesso Embargado"],"dc:subject":["Lapachol","Quinona","Triazol","Composto heterocíclico","Naftoquinona Derivados","Lapachona.","Quinone","Triazole"],"dc:title":["SÍNTESE DE NOVOS DERIVADOS DE LAPACHONAS E NOR-LAPACHONAS: VEREDAS À ATIVIDADE FARMACOLÓGICA"],"dc:type":["Dissertação"]},"updated_at":"2026-07-27T19:00:28Z"}