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[BMIM][OH]-Mediated One-Pot Synthesis of 2-Amino-5-oxo-4-(1H-pyrazol-5-yl)-5H-chromeno[4,3-b]pyridine-3-carbonitriles as Potential Anticancer Agents
A series of 2-amino-5-oxo-4-(1 H -pyrazol-5-yl)-5 H -chromeno[4,3- b ]pyridine-3-carbonitriles was synthesized with good yields of 87–90% by reacting 4-amino-2 H -chromen-2-one with 1 H -pyrazole-5-carbaldehyde and malononitrile at 70–75°C for 120–150 min using BMIM[OH] as ionic liquid. Cytotoxic ac...
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Published in: | Russian journal of general chemistry 2023, Vol.93 (1), p.227-233 |
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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: | A series of 2-amino-5-oxo-4-(1
H
-pyrazol-5-yl)-5
H
-chromeno[4,3-
b
]pyridine-3-carbonitriles was synthesized with good yields of 87–90% by reacting 4-amino-2
H
-chromen-2-one with 1
H
-pyrazole-5-carbaldehyde and malononitrile at 70–75°C for 120–150 min using BMIM[OH] as ionic liquid. Cytotoxic activity of the synthesized derivatives against PC-3 and HepG2 cells was evaluated. Among synthesized, 2-amino-9-ethyl-4-(1-methyl/ethyl-1
H
-pyrazol-5-yl)-5-oxo-5
H
-chromeno[4,3-
b
]pyridine-3-carbonitriles were identified as most active compounds: IC
50
values of 9.2 and 8.9 µM against PC-3 and HepG2 cells, respectively. In addition, we evaluated the binding affinity of these compounds towards human carbonic anhydrase protein (PDB ID: 5BNL). The binding energy was found to be –7.1 kcal/mol for 2-amino-9-ethyl-4-(1-methyl-1
H
-pyrazol-5-yl)-5-oxo-5
H
-chromeno[4,3-
b
]pyridine-3-carbonitrile, which is higher than positive control co-crystal ligand 2HC (–5.4 kcal/mol). |
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ISSN: | 1070-3632 1608-3350 |
DOI: | 10.1134/S1070363223010279 |