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3-hydroxy-3-(1H-indol-3-yl)-5-nitrooxindole and derivative
The 3-hydroxy-3-(1H-indol-3-yl)-5-nitrooxindole (3) has been obtained in 88% yield from a reaction of 5-nitroisatin (1) and indole (2) using potassium carbonate as the catalyst. The catalytic reduction of 3 with hydrazine monohydrate and Pd/C catalyst produced 5-amino-3-hydroxy-3-(1H-indol-3-yl)oxin...
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Main Authors: | , , , , , |
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Format: | Conference Proceeding |
Language: | English |
Subjects: | |
Online Access: | Get full text |
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Summary: | The 3-hydroxy-3-(1H-indol-3-yl)-5-nitrooxindole (3) has been obtained in 88% yield from a reaction of 5-nitroisatin (1) and indole (2) using potassium carbonate as the catalyst. The catalytic reduction of 3 with hydrazine monohydrate and Pd/C catalyst produced 5-amino-3-hydroxy-3-(1H-indol-3-yl)oxindole (4) in 79% yield. The structure of 3 and 4 was justified by FT-IR, 1H/13C NMR, and mass spectroscopies. The cytotoxicity assay of 3 and 4 on HepG2 cells indicated that compound 3 (IC50 0.39 mM) is more active than 4 (IC50 3.56 mM). The molecular docking studies of 3 dan 4 in the binding site of VEGFR2 kinase (PDB ID: 5EW3) showed that the binding energy of compound 3 (-9.1 kcal/mol) was better than that of compound 4 (-8.45 kcal/mol). According to their binding pose, both can be classified as type II kinase inhibitors against VEGFR2 kinase (PDB ID: 5EW3). |
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ISSN: | 0094-243X 1551-7616 |
DOI: | 10.1063/5.0205816 |