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Novel polyhydroquinoline Schiff’s base derivatives: synthesis, characterization, in vitro α-glucosidase inhibitory, and molecular docking studies
Novel Schiff’s base hydrazone derivatives (1–24) based on polyhydroquinoline (PHQ) were synthesized in good to excellent yields via three step reactions. Compound 1 (starting material) was synthesized through one pot multi-component unsymmetrical Hantzsch reaction by refluxing a mixture of ethyl-2-(...
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Published in: | Research on chemical intermediates 2023-07, Vol.49 (7), p.3005-3028 |
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Main Authors: | , , , , , , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | Novel Schiff’s base hydrazone derivatives
(1–24)
based on polyhydroquinoline (PHQ) were synthesized in good to excellent yields via three step reactions. Compound
1
(starting material) was synthesized through one pot multi-component unsymmetrical Hantzsch reaction by refluxing a mixture of ethyl-2-(2-formylphenoxy)acetate, dimedone, ammonium acetate, and ethyl acetoacetate in ethanol solvent for 6–8 h. The obtained PHQ was then refluxed with hydrazine hydrate in the presence of absolute ethanol for 4–5 h. to get compound
2
. Finally, the hydrazide was treated with various substituted aromatic/aliphatic aldehydes to afford the desired hydrazone Schiff’s bases
(3–24)
. All the produced analogues were structurally deduced with the help of LC-HRESI-MS,
1
H- and
13
C-NMR spectroscopy. The obtained compounds were evaluated for their α-glucosidase activity, where twelve compounds (
10, 14, 7, 9, 8, 17, 12, 19, 13, 15, 21,
and
11)
were found the most active at IC
50
ranging between 5.26 and 25.17 µM, compared to acarbose, a standard α-glucosidase inhibitor with IC
50
of 873.34 ± 1.67 µM. The best hit compounds were docked within the acarbose binding pocket of α-glucosidase and vetted for their binding affinities. |
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ISSN: | 0922-6168 1568-5675 |
DOI: | 10.1007/s11164-023-05038-y |