Publication
Application of PEG400 in the one-pot synthesis of 7-[4-alkyl- or (hetero)aryl-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridines via SNAr and Cu(I)-Catalyzed Azide-Alkyne Cycloaddition and preliminary evaluation of their anti-tumour activity
| dc.contributor.author | Rodrigues, Juliana M. | |
| dc.contributor.author | Calhelha, Ricardo C. | |
| dc.contributor.author | Ferreira, Isabel C.F.R. | |
| dc.contributor.author | Queiroz, Maria João R.P. | |
| dc.date.accessioned | 2018-02-19T10:00:00Z | |
| dc.date.accessioned | 2021-02-27T17:37:52Z | |
| dc.date.available | 2018-01-19T10:00:00Z | |
| dc.date.available | 2021-02-27T17:37:52Z | |
| dc.date.issued | 2020 | |
| dc.description.abstract | Several novel 7-[4-alkyl- or (hetero)aryl-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridines were prepared in good to high yields, using the environmentally friendly solvent PEG400 in a one-pot procedure from 7-chlorothieno[3,2-b]pyridine to form the corresponding azide via SNAr with NaN3, followed by Cu(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) using different types of alkynes. This one-pot reaction in PEG400 starting from a halogenated heteroaromatic system is reported for the first time and demonstrated a wide scope of application for alkynes. Preliminary anti-tumour activity on human tumour cell lines using the prepared 1,4-di(hetero)aryl-1,2,3-triazoles was evaluated, together with their toxicity in non-tumour cells. Among the tested compounds the most promising one was a 2-ethynylpyridine derivative. | en_EN |
| dc.description.version | info:eu-repo/semantics/publishedVersion | en_EN |
| dc.identifier.citation | Rodrigues, Juliana M.; Calhelha, Ricardo C.; Ferreira, Isabel C.F.R.; Queiroz, Maria João R.P. (2020). Application of PEG400 in the one-pot synthesis of 7-[4-alkyl- or (hetero)aryl-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridines via SNAr and Cu(I)-Catalyzed Azide-Alkyne Cycloaddition and preliminary evaluation of their anti-tumour activity. Tetrahedron Letters. ISSN 0040-4039. 61:22, p. 1-4 | en_EN |
| dc.identifier.doi | 10.1016/j.tetlet.2020.151900 | en_EN |
| dc.identifier.issn | 0040-4039 | |
| dc.identifier.uri | http://hdl.handle.net/10198/23415 | |
| dc.language.iso | eng | |
| dc.peerreviewed | yes | en_EN |
| dc.subject | 1, 4-Disubstituted-1,2, 3-triazoles | en_EN |
| dc.subject | CuAAC | en_EN |
| dc.subject | PEG 400 | en_EN |
| dc.subject | Thieno[3, 2-b] pyridines | en_EN |
| dc.title | Application of PEG400 in the one-pot synthesis of 7-[4-alkyl- or (hetero)aryl-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridines via SNAr and Cu(I)-Catalyzed Azide-Alkyne Cycloaddition and preliminary evaluation of their anti-tumour activity | en_EN |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| person.familyName | Calhelha | |
| person.familyName | Ferreira | |
| person.givenName | Ricardo C. | |
| person.givenName | Isabel C.F.R. | |
| person.identifier | 144781 | |
| person.identifier.ciencia-id | F313-E3CE-554E | |
| person.identifier.ciencia-id | 9418-CF95-9919 | |
| person.identifier.orcid | 0000-0002-6801-4578 | |
| person.identifier.orcid | 0000-0003-4910-4882 | |
| person.identifier.rid | J-2172-2014 | |
| person.identifier.rid | E-8500-2013 | |
| person.identifier.scopus-author-id | 6507978333 | |
| person.identifier.scopus-author-id | 36868826600 | |
| rcaap.rights | openAccess | en_EN |
| rcaap.type | article | en_EN |
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| relation.isAuthorOfPublication.latestForDiscovery | 2d5d1a41-7561-4a01-871c-b4c97da35053 |