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 journalConference articlepeer-review


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 languageEnglish
Article number020039
JournalAIP Conference Proceedings
Issue number1
Publication statusPublished - 11 Apr 2024
Event5th International Seminar on Chemistry, ISoC 2022 - Surabaya, Indonesia
Duration: 12 Oct 202213 Oct 2022


  • anticancer HepG2
  • disease
  • molecular docking
  • oxindoles
  • synthesis


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