Synthesis, in vitro antigiardial activity, SAR analysis and docking study of substituted chalcones
Abstract A series of 15 chalcones-bearing substituents at positions 2, 4, and 5 of rings A and B were synthesized using microwave-assisted Claissen–Smichdt condensation and evaluated for their activity against Giardia lamblia and Green monkey kidney cells. Five compounds exhibited activity against G. lamblia at $ IC_{50} $’s <5 μM. The chalcone 3m exhibited the highest antigiardial activity ($ IC_{50} $ = 1.03 μM), even more than the positive control (metronidazole, $ IC_{50} $ = 1.4 μM), and selectivity (SI = 38.9). A preliminary SAR study suggested that electrophylicity has not relationship with antigiardiasic activity, and the docking study reveals that synthesized chalcones bind at zone 3 of colchicine site, therefore presumably the action mechanism of the synthesized chalcones does not follow the Michael acceptor mechanism..
| Medienart: |
Artikel |
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| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:29 |
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| Enthalten in: |
Medicinal chemistry research - 29(2019), 3 vom: 27. Dez., Seite 431-441 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Cáceres-Castillo, David [VerfasserIn] |
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| Links: |
Volltext [lizenzpflichtig] |
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| Themen: |
Antigiardial activity |
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| Anmerkungen: |
© Springer Science+Business Media, LLC, part of Springer Nature 2020 |
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| doi: |
10.1007/s00044-019-02492-5 |
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| funding: |
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| PPN (Katalog-ID): |
OLC2049382367 |
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| 520 | |a Abstract A series of 15 chalcones-bearing substituents at positions 2, 4, and 5 of rings A and B were synthesized using microwave-assisted Claissen–Smichdt condensation and evaluated for their activity against Giardia lamblia and Green monkey kidney cells. Five compounds exhibited activity against G. lamblia at $ IC_{50} $’s <5 μM. The chalcone 3m exhibited the highest antigiardial activity ($ IC_{50} $ = 1.03 μM), even more than the positive control (metronidazole, $ IC_{50} $ = 1.4 μM), and selectivity (SI = 38.9). A preliminary SAR study suggested that electrophylicity has not relationship with antigiardiasic activity, and the docking study reveals that synthesized chalcones bind at zone 3 of colchicine site, therefore presumably the action mechanism of the synthesized chalcones does not follow the Michael acceptor mechanism. | ||
| 650 | 4 | |a Synthesis | |
| 650 | 4 | |a Substituted chalcones | |
| 650 | 4 | |a Antigiardial activity | |
| 650 | 4 | |a SAR analysis | |
| 650 | 4 | |a Docking study | |
| 700 | 1 | |a Carballo, Rubén M. |4 aut | |
| 700 | 1 | |a Quijano-Quiñones, Ramiro |4 aut | |
| 700 | 1 | |a Mirón-López, Gumersindo |4 aut | |
| 700 | 1 | |a Graniel-Sabido, Manlio |4 aut | |
| 700 | 1 | |a Moo-Puc, Rosa E. |4 aut | |
| 700 | 1 | |a Mena-Rejón, Gonzalo J. |0 (orcid)0000-0003-4248-2274 |4 aut | |
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