Publication
Synthesis of β-benzo[b]thienyldehydrophenylalanine derivatives by one-pot palladium-catalyzed borylation and suzuki coupling (BSC) and metal-assisted intramolecular cyclization: studies of fluorescence and antimicrobial activity
| dc.contributor.author | Abreu, Ana S. | |
| dc.contributor.author | Ferreira, Paula M.T. | |
| dc.contributor.author | Queiroz, Maria João R.P. | |
| dc.contributor.author | Ferreira, Isabel C.F.R. | |
| dc.contributor.author | Calhelha, Ricardo C. | |
| dc.contributor.author | Estevinho, Leticia M. | |
| dc.date.accessioned | 2008-09-12T14:33:01Z | |
| dc.date.available | 2008-09-12T14:33:01Z | |
| dc.date.issued | 2005 | |
| dc.description.abstract | Palladium-catalyzed borylation and Suzuki coupling (BSC) in a one-pot procedure was successfully applied to the synthesis of several β-substituted dehydrophenylalanines in the benzo[b]thiophene series, with the stereochemistry of the starting materials being maintained. Bromobenzo[b]thiophenes bearing an ortho EDG (OMe or Me) were used as the components to be borylated with pinacolborane, whilst pure stereoisomers of β-bromodehydrophenylalanines were used as the other Suzuki coupling components. Treatment of the obtained methyl ester of (Z)-N-(tert-butoxycarbonyl)-β- (2,3,5-trimethylbenzo[b]thien-6-yl)dehydrophenylalanine with Pd(OAc)2 and Cu(OAc)2 in DMF at 160 °C gave two in dole derivatives (1:3), the major product resulting from isomerization and cyclization and the minor product resulting from direct cyclization (thienoindole). Carrying out the reaction at 100 °C gave the same products in similar amounts. Use of the methyl ester of (Z)-N-(tert-butoxycarbonyl)-β- (2,3,7-trimethylbenzo[b]thien-6-yl)dehydrophenylalanine as starting material gave only one product, resulting from isomerization and cyclization at 100 °C. Two of the cyclized compounds were subjected to fluorescence studies; the thienoindole could be useful as a fluorescent probe. Preliminary studies of antimicrobial activity were performed on the precursors and on the cyclized products. | en |
| dc.identifier.citation | Abreu, Ana S.; Ferreira, Paula M.T.; Queiroz, Maria João R.P.; Ferreira, Isabel C.F.R.; Calhelha, Ricardo C.; Estevinho, Leticia M. (2005). Synthesis of β - benzo[b]thienyldehydrophenylalanine derivatives by one-pot palladium-catalyzed borylation and suzuki coupling (BSC) and metal-assisted intramolecular cyclization: studies of fluorescence and antimicrobial activity. European Journal of Organic Chemistry. ISSN 1434-193X. 2005:14. p. 2951-2957 | en |
| dc.identifier.doi | 10.1002/ejoc.200500040 | |
| dc.identifier.issn | 1434-193X | |
| dc.identifier.uri | http://hdl.handle.net/10198/823 | |
| dc.language.iso | eng | en |
| dc.publisher | Wiley Interscience | en |
| dc.relation | Synthesis of non-proteinogenic amino acids with biological and/or photochromic activities | |
| dc.relation | SÍNTESE DE NOVOS FOTOBIOSSENSORES DERIVADOS DE AMINOÁCIDOS BENZO b TIOFÉNICOS | |
| dc.subject | Dehydrophenylalanines | en |
| dc.subject | Benzothiophenes | en |
| dc.subject | Borylation | en |
| dc.subject | Suzuki coupling | en |
| dc.subject | Cyclization | en |
| dc.subject | Indoles | en |
| dc.subject | Fluorescence | en |
| dc.subject | Antimicrobial activity | en |
| dc.title | Synthesis of β-benzo[b]thienyldehydrophenylalanine derivatives by one-pot palladium-catalyzed borylation and suzuki coupling (BSC) and metal-assisted intramolecular cyclization: studies of fluorescence and antimicrobial activity | en |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.awardTitle | Synthesis of non-proteinogenic amino acids with biological and/or photochromic activities | |
| oaire.awardTitle | SÍNTESE DE NOVOS FOTOBIOSSENSORES DERIVADOS DE AMINOÁCIDOS BENZO b TIOFÉNICOS | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/POCI/POCTI%2FQUI%2F32689%2F2000/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F4709%2F2001/PT | |
| oaire.fundingStream | POCI | |
| person.familyName | Ferreira | |
| person.familyName | Calhelha | |
| person.familyName | Estevinho | |
| person.givenName | Isabel C.F.R. | |
| person.givenName | Ricardo C. | |
| person.givenName | Letícia M. | |
| person.identifier | 144781 | |
| person.identifier.ciencia-id | 9418-CF95-9919 | |
| person.identifier.ciencia-id | F313-E3CE-554E | |
| person.identifier.ciencia-id | BA14-09D6-A406 | |
| person.identifier.orcid | 0000-0003-4910-4882 | |
| person.identifier.orcid | 0000-0002-6801-4578 | |
| person.identifier.orcid | 0000-0002-9249-1948 | |
| person.identifier.rid | E-8500-2013 | |
| person.identifier.rid | J-2172-2014 | |
| person.identifier.scopus-author-id | 36868826600 | |
| person.identifier.scopus-author-id | 6507978333 | |
| person.identifier.scopus-author-id | 6506577664 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| rcaap.rights | openAccess | |
| rcaap.type | article | en |
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