5-Aminoindole

Chemical Properties

Uses

Uses

• Smac mimetics that bind to the BIR2 domain of the anti-apoptotic protein XIAP
• Cytotoxic and antimitotic agents
• Insulin-like growth factor 1 receptor inhibitors
• Antitumoral agents
• Factor Xa inhibitor
• Potential antivascular agents
• Gli1-mediated transcription in the Hedgehog pathway
• Inhibitors of receptor tyrosine kinase with antiangiogenic effects
• PKCθ inhibitors
• HIV protease inhibitors

Definition

Synthesis

6146-52-7

5192-03-0

In Example 1, 5-nitroindole was substituted for m-nitroacetophenone as a raw material, maintaining a molar ratio of 1:1. The reaction was carried out at 80 °C for 24 h under hydrogen pressure of 4.0 MPa. Other conditions were consistent with Example 1, and 5-aminoindole was finally obtained in 98% yield. This was done as follows: 16.44 mg (0.04 mmol) of silver 4,4'-dimethoxy-2,2'-bipyridine, 11.22 mg (0.1 mmol) of potassium tert-butanolate and 1 ml of 1,4-dioxane solution were added to an autoclave. After thorough stirring, 165.15 mg (1 mmol) of m-nitroacetophenone was added and the mixture was stirred and reacted at 80 °C for 8 hours. Upon completion of the reaction, the reaction solution was extracted with deionized water and dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous Na2SO4 and then subjected to filtration, rotary evaporation and chromatographic separation to afford 3-acetanilide as a yellow solid in 96% yield.

References