Publicação
Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine
| Resumo: | The acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition activities of a series of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro[2,3-b]quinolines (10-12)/4-amino-5,6,7,8-tetrahydro-2,3-diphenylthieno[2,3-b]quinoline (14) and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo[2,3-b]pyridine (13)/4amino-5,6,7,8,9-pentahydro-2,3-phenylcyclohepta[e]thieno[2,3-b]pyridine (15) are described. These compounds are tacrine (THA) analogues which have been prepared either from readily available 2-amino-3-cyano-4,5-diarylfurans (16-18) or from 2-amino-3-cyano-4,5-diphenylthiophene (19), via Friedlander condensation with cyclohexanone or cycloheptanone. These compounds are competitive inhibitors for acetylcholinesterase, the more potent being compound (13) which is threefold less active than tacrine. The butyrylcholinesterase inhibition activity is significant only in compounds 10 and 13, which are ten-fold less active than tacrine. It is found that the products 11 and 12 strongly inhibit acetylcholinesterase, and show excellent selectivity regarding butyrylcholinesterase. |
|---|---|
| Autores principais: | Marco, JL |
| Outros Autores: | de los Rios, C; Carreiras, MC; Banos, JE; Badia, A; Vivas, NM |
| Assunto: | Chemistry, Medicinal Chemistry, Multidisciplinary Pharmacology & Pharmacy |
| Ano: | 2002 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso a metadados |
| Instituição associada: | Universidade de Lisboa |
| Idioma: | inglês |
| Origem: | Repositório da Universidade de Lisboa |
| _version_ | 1865920840646787072 |
|---|---|
| author | Marco, JL |
| author2 | de los Rios, C Carreiras, MC Banos, JE Badia, A Vivas, NM |
| author2_role | author author author author author |
| author_facet | Marco, JL Marco, JL de los Rios, C Carreiras, MC Banos, JE Badia, A Vivas, NM de los Rios, C Carreiras, MC Banos, JE Badia, A Vivas, NM |
| author_role | author |
| contributor_name_str_mv | Repositório Científico de Acesso Aberto da ULisboa |
| country_str | PT |
| creators_json_str | [{\"Person.name\":\"Marco, JL\"},{\"Person.name\":\"de los Rios, C\"},{\"Person.name\":\"Carreiras, MC\"},{\"Person.name\":\"Banos, JE\"},{\"Person.name\":\"Badia, A\"},{\"Person.name\":\"Vivas, NM\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Repositório Científico de Acesso Aberto da ULisboa |
| datacite.creators.creator.creatorName.fl_str_mv | Marco, JL de los Rios, C Carreiras, MC Banos, JE Badia, A Vivas, NM |
| datacite.date.Accepted.fl_str_mv | 2002-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2015-12-30T10:18:03Z |
| datacite.date.embargoed.fl_str_mv | 2015-12-30T10:18:03Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_14cb |
| datacite.subjects.subject.fl_str_mv | Chemistry, Medicinal Chemistry, Multidisciplinary Pharmacology & Pharmacy |
| datacite.titles.title.fl_str_mv | Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine |
| dc.contributor.none.fl_str_mv | Repositório Científico de Acesso Aberto da ULisboa |
| dc.creator.none.fl_str_mv | Marco, JL de los Rios, C Carreiras, MC Banos, JE Badia, A Vivas, NM |
| dc.date.Accepted.fl_str_mv | 2002-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2015-12-30T10:18:03Z |
| dc.date.embargoed.fl_str_mv | 2015-12-30T10:18:03Z |
| dc.identifier.none.fl_str_mv | http://hdl.handle.net/10451/21380 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | WILEY-V C H VERLAG GMBH |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_14cb |
| dc.subject.none.fl_str_mv | Chemistry, Medicinal Chemistry, Multidisciplinary Pharmacology & Pharmacy |
| dc.title.fl_str_mv | Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | The acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition activities of a series of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro[2,3-b]quinolines (10-12)/4-amino-5,6,7,8-tetrahydro-2,3-diphenylthieno[2,3-b]quinoline (14) and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo[2,3-b]pyridine (13)/4amino-5,6,7,8,9-pentahydro-2,3-phenylcyclohepta[e]thieno[2,3-b]pyridine (15) are described. These compounds are tacrine (THA) analogues which have been prepared either from readily available 2-amino-3-cyano-4,5-diarylfurans (16-18) or from 2-amino-3-cyano-4,5-diphenylthiophene (19), via Friedlander condensation with cyclohexanone or cycloheptanone. These compounds are competitive inhibitors for acetylcholinesterase, the more potent being compound (13) which is threefold less active than tacrine. The butyrylcholinesterase inhibition activity is significant only in compounds 10 and 13, which are ten-fold less active than tacrine. It is found that the products 11 and 12 strongly inhibit acetylcholinesterase, and show excellent selectivity regarding butyrylcholinesterase. |
| dirty | 0 |
| eu_rights_str_mv | metadataOnlyAccess |
| format | article |
| id | ul_d63bcbd2f4f08a816efb90d3b2c48caf |
| identifier.url.fl_str_mv | http://hdl.handle.net/10451/21380 |
| instacron_str | ul |
| institution | Universidade de Lisboa |
| instname_str | Universidade de Lisboa |
| language | eng |
| network_acronym_str | ul |
| network_name_str | Repositório da Universidade de Lisboa |
| oai_identifier_str | oai:repositorio.ulisboa.pt:10451/21380 |
| organization_str_mv | urn:organizationAcronym:ul |
| person_str_mv | Marco, JL de los Rios, C Carreiras, MC Banos, JE Badia, A Vivas, NM |
| publishDate | 2002 |
| publisher.none.fl_str_mv | WILEY-V C H VERLAG GMBH |
| reponame_str | Repositório da Universidade de Lisboa |
| repository_id_str | urn:repositoryAcronym:ul |
| service_str_mv | urn:repositoryAcronym:ul |
| spelling | engWILEY-V C H VERLAG GMBHThe acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition activities of a series of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro[2,3-b]quinolines (10-12)/4-amino-5,6,7,8-tetrahydro-2,3-diphenylthieno[2,3-b]quinoline (14) and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo[2,3-b]pyridine (13)/4amino-5,6,7,8,9-pentahydro-2,3-phenylcyclohepta[e]thieno[2,3-b]pyridine (15) are described. These compounds are tacrine (THA) analogues which have been prepared either from readily available 2-amino-3-cyano-4,5-diarylfurans (16-18) or from 2-amino-3-cyano-4,5-diphenylthiophene (19), via Friedlander condensation with cyclohexanone or cycloheptanone. These compounds are competitive inhibitors for acetylcholinesterase, the more potent being compound (13) which is threefold less active than tacrine. The butyrylcholinesterase inhibition activity is significant only in compounds 10 and 13, which are ten-fold less active than tacrine. It is found that the products 11 and 12 strongly inhibit acetylcholinesterase, and show excellent selectivity regarding butyrylcholinesterase.Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridineMarco, JLde los Rios, CCarreiras, MCBanos, JEBadia, AVivas, NMHostingInstitutionOrganizationalRepositório Científico de Acesso Aberto da ULisboae-mailmailto:repositorio@reitoria.ulisboa.ptrepositorio@reitoria.ulisboa.ptISSNIsPartOf0365-62332015-12-30T10:18:03Z20022002-01-01T00:00:00ZHandlehttp://hdl.handle.net/10451/21380http://purl.org/coar/access_right/c_14cbmetadata only accessChemistry, MedicinalChemistry, MultidisciplinaryPharmacology & Pharmacyliteraturehttp://purl.org/coar/resource_type/c_6501journal articleARCHIV DER PHARMAZIEVol. 335347353 |
| spellingShingle | Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine Marco, JL Chemistry, Medicinal Chemistry, Multidisciplinary Pharmacology & Pharmacy Marco, JL Chemistry, Medicinal Chemistry, Multidisciplinary Pharmacology & Pharmacy |
| status | SINGLETON |
| subject.fl_str_mv | Chemistry, Medicinal Chemistry, Multidisciplinary Pharmacology & Pharmacy |
| title | Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine |
| title_full | Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine |
| title_fullStr | Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine |
| title_full_unstemmed | Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine |
| title_short | Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine |
| title_sort | Synthesis and acetylcholinesterase/butyrylcholin-esterase inhibition activity of 4-amino-2,3-diaryl-5,6,7,8-tetrahydrofuro(and thieno)[2,3-b]quinolines, and 4-amino-5,6,7,8,9-pentahydro-2,3-diphenylcyclohepta[e]furo(and thieno)-[2,3-b]pyridine |
| topic | Chemistry, Medicinal Chemistry, Multidisciplinary Pharmacology & Pharmacy |
| topic_facet | Chemistry, Medicinal Chemistry, Multidisciplinary Pharmacology & Pharmacy |
| url | http://hdl.handle.net/10451/21380 |
| visible | 1 |