3-hydroxy-3-(1H-indol-3-yl)-5-nitrooxindole and derivative

Arif Fadlan; Nila Huda; First Ambar Wati; Nur Pasca Aijijiyah; Azminah Azminah; Mardi Santoso

doi:10.1063/5.0205816

3-hydroxy-3-(1H-indol-3-yl)-5-nitrooxindole and derivative

Arif Fadlan, Nila Huda, First Ambar Wati, Nur Pasca Aijijiyah, Azminah Azminah, Mardi Santoso^*

^*Corresponding author for this work

Research output: Contribution to journal › Conference article › peer-review

Abstract

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).

Original language	English
Article number	020039
Journal	AIP Conference Proceedings
Volume	3071
Issue number	1
DOIs	https://doi.org/10.1063/5.0205816
Publication status	Published - 11 Apr 2024
Event	5th International Seminar on Chemistry, ISoC 2022 - Surabaya, Indonesia Duration: 12 Oct 2022 → 13 Oct 2022

Keywords

anticancer HepG2
disease
molecular docking
oxindoles
synthesis

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10.1063/5.0205816

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title = "3-hydroxy-3-(1H-indol-3-yl)-5-nitrooxindole and derivative",

abstract = "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).",

keywords = "anticancer HepG2, disease, molecular docking, oxindoles, synthesis",

author = "Arif Fadlan and Nila Huda and Wati, {First Ambar} and Aijijiyah, {Nur Pasca} and Azminah Azminah and Mardi Santoso",

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AU - Fadlan, Arif

AU - Huda, Nila

AU - Wati, First Ambar

AU - Aijijiyah, Nur Pasca

AU - Azminah, Azminah

AU - Santoso, Mardi

PY - 2024/4/11

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N2 - 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).

AB - 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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ER -

3-hydroxy-3-(1H-indol-3-yl)-5-nitrooxindole and derivative

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