Synthesis and evaluation of novel chromanone and quinolinone analogues of uniflorol as anti-leishmanial agents
Within this work, we describe the design and synthesis of a range of novel chromanones and quinolinones, based on natural products reported to possess anti-leishmanial action. The core heterocycles were obtained either via classical or ionic liquid mediated Kabbe condensation in the case of chromano...
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| Format: | Article |
| Language: | English |
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Elsevier
2020-03-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S240584402030459X |
| _version_ | 1818204896304824320 |
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| author | Helena Castro Tânia Cruz Patrícia de Aguiar Amaral Paula da Silva Cardoso Ahmed Alsaffar Patrick Farrell Ana M. Tomás James W. Barlow |
| author_facet | Helena Castro Tânia Cruz Patrícia de Aguiar Amaral Paula da Silva Cardoso Ahmed Alsaffar Patrick Farrell Ana M. Tomás James W. Barlow |
| author_sort | Helena Castro |
| collection | DOAJ |
| description | Within this work, we describe the design and synthesis of a range of novel chromanones and quinolinones, based on natural products reported to possess anti-leishmanial action. The core heterocycles were obtained either via classical or ionic liquid mediated Kabbe condensation in the case of chromanones, or aqueous Sonogashira based alkynylation followed by acid-catalysed cyclisation in the case of quinolinones. Upon testing in promastigotes, axenic amastigotes and Leishmania-infected macrophages, compound 13c was identified as displaying interesting activity, inhibiting axenic amastigotes and intracellular amastigotes with IC50s of 25.3 and 24.6μM respectively. |
| first_indexed | 2024-12-12T03:48:31Z |
| format | Article |
| id | doaj.art-f7582228890e4ef49dd7c7ad7a84ae0f |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-12-12T03:48:31Z |
| publishDate | 2020-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-f7582228890e4ef49dd7c7ad7a84ae0f2022-12-22T00:39:28ZengElsevierHeliyon2405-84402020-03-0163e03614Synthesis and evaluation of novel chromanone and quinolinone analogues of uniflorol as anti-leishmanial agentsHelena Castro0Tânia Cruz1Patrícia de Aguiar Amaral2Paula da Silva Cardoso3Ahmed Alsaffar4Patrick Farrell5Ana M. Tomás6James W. Barlow7i3S - Instituto de Investigação e Inovação em Saúde, Universidade do Porto, Rua Alfredo Allen 208, 4200-135 Porto, Portugal; IBMC – Instituto de Biologia Molecular e Celular, Universidade do Porto, Rua Alfredo Allen, 208, 4200-135 Porto, Portugali3S - Instituto de Investigação e Inovação em Saúde, Universidade do Porto, Rua Alfredo Allen 208, 4200-135 Porto, Portugal; IBMC – Instituto de Biologia Molecular e Celular, Universidade do Porto, Rua Alfredo Allen, 208, 4200-135 Porto, PortugalLaboratory of Medicinal Plants (LaPlaM/ PPGCA), Universidade do Extremo Sul Catarinense (UNESC), Avenida Universitária 1105, Bairro Universitário, 88806-000 Criciúma, SC, BrazilLaboratory of Medicinal Plants (LaPlaM/ PPGCA), Universidade do Extremo Sul Catarinense (UNESC), Avenida Universitária 1105, Bairro Universitário, 88806-000 Criciúma, SC, Brazil; Department of Chemistry, RCSI, 123 St. Stephen's Green, Dublin 2, IrelandDepartment of Chemistry, RCSI, 123 St. Stephen's Green, Dublin 2, IrelandDepartment of Chemistry, RCSI, 123 St. Stephen's Green, Dublin 2, Irelandi3S - Instituto de Investigação e Inovação em Saúde, Universidade do Porto, Rua Alfredo Allen 208, 4200-135 Porto, Portugal; IBMC – Instituto de Biologia Molecular e Celular, Universidade do Porto, Rua Alfredo Allen, 208, 4200-135 Porto, Portugal; ICBAS - Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, PortugalDepartment of Chemistry, RCSI, 123 St. Stephen's Green, Dublin 2, Ireland; Corresponding author.Within this work, we describe the design and synthesis of a range of novel chromanones and quinolinones, based on natural products reported to possess anti-leishmanial action. The core heterocycles were obtained either via classical or ionic liquid mediated Kabbe condensation in the case of chromanones, or aqueous Sonogashira based alkynylation followed by acid-catalysed cyclisation in the case of quinolinones. Upon testing in promastigotes, axenic amastigotes and Leishmania-infected macrophages, compound 13c was identified as displaying interesting activity, inhibiting axenic amastigotes and intracellular amastigotes with IC50s of 25.3 and 24.6μM respectively.http://www.sciencedirect.com/science/article/pii/S240584402030459XNatural product chemistryOrganic chemistryPharmaceutical chemistryChromanoneQuinolinoneLeishmania |
| spellingShingle | Helena Castro Tânia Cruz Patrícia de Aguiar Amaral Paula da Silva Cardoso Ahmed Alsaffar Patrick Farrell Ana M. Tomás James W. Barlow Synthesis and evaluation of novel chromanone and quinolinone analogues of uniflorol as anti-leishmanial agents Heliyon Natural product chemistry Organic chemistry Pharmaceutical chemistry Chromanone Quinolinone Leishmania |
| title | Synthesis and evaluation of novel chromanone and quinolinone analogues of uniflorol as anti-leishmanial agents |
| title_full | Synthesis and evaluation of novel chromanone and quinolinone analogues of uniflorol as anti-leishmanial agents |
| title_fullStr | Synthesis and evaluation of novel chromanone and quinolinone analogues of uniflorol as anti-leishmanial agents |
| title_full_unstemmed | Synthesis and evaluation of novel chromanone and quinolinone analogues of uniflorol as anti-leishmanial agents |
| title_short | Synthesis and evaluation of novel chromanone and quinolinone analogues of uniflorol as anti-leishmanial agents |
| title_sort | synthesis and evaluation of novel chromanone and quinolinone analogues of uniflorol as anti leishmanial agents |
| topic | Natural product chemistry Organic chemistry Pharmaceutical chemistry Chromanone Quinolinone Leishmania |
| url | http://www.sciencedirect.com/science/article/pii/S240584402030459X |
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