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. |
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| 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 |
| 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. |
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