Biological Functions
6-Bromoisatin inhibited proliferation of HT29 cells at IC50 223 μM (0.05 mg/mL) and induced apoptosis without increasing caspase 3/7 activity. In vivo 6-bromoisatin (0.05 mg/g) was found to significantly enhance the apoptotic index (p ≤ 0.001) and reduced cell proliferation (p ≤ 0.01) in the distal colon.
Synthesis
Step 2: N-(3-bromophenyl)-2-hydroxyiminoacetamide (55 g, 0.2272 mol) was added to concentrated sulfuric acid (275 mL) and the temperature was maintained at 50 °C. The temperature of the reaction system was then raised to 90 °C for 3 hours. Upon completion of the reaction, the reaction mixture was slowly poured into ice water and a yellow precipitate was precipitated. The precipitate was collected by filtration and dried to give 6-bromodihydroindole-2,3-dione as a yellow solid (50 g, 98% yield). The resulting product can be used directly in the subsequent reaction without further purification.
References
[1] Patent: WO2012/58671, 2012, A1. Location in patent: Page/Page column 91
[2] Patent: WO2011/119704, 2011, A1. Location in patent: Page/Page column 36-37
[3] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 549 - 554
[4] Medicinal Chemistry, 2014, vol. 10, # 5, p. 484 - 496
[5] Patent: US2014/38952, 2014, A1. Location in patent: Page/Page column 0154-0155
