55191-22-5

Basic information

• Product Name: 1-Acetyl-1H-indole-3-acetic acid methyl ester
• Synonyms: 1-Acetyl-1H-indole-3-acetic acid methyl ester
• CAS NO: 55191-22-5
• Molecular Formula: C₁₃H₁₃NO₃
• Molecular Weight: 231.25
• Mol File: 55191-22-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Acetyl-1H-indole-3-acetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Acetyl-1H-indole-3-acetic acid methyl ester(55191-22-5)
• EPA Substance Registry System: 1-Acetyl-1H-indole-3-acetic acid methyl ester(55191-22-5)

Safety Data

• Hazardous Substances Data: 55191-22-5(Hazardous Substances Data)

Upstream product

• 87-51-4 indole-3-acetic acid 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 108-24-7 acetic anhydride 
• 129177-60-2 (Z)-1-Acetyl-2-methoxy-3-methoxycarbonylmethylene-2,3-dihydroindole 
• 16800-68-3 1-acetyl-2,3-dihydro-1H-indol-3-one 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Relevant articles and documents

The "gatekeeper" Residue Influences the Mode of Binding of Acetyl Indoles to Bromodomains

Small-molecule hits for the bromodomains of CREBBP and BAZ2B have been identified by scaffold hopping followed by docking of a set of ～200 compounds containing the acetyl indole scaffold. Chemical synthesis of nearly 30 derivatives has resulted in ligands of representatives of three subfamilies of human bromodomains with favorable ligand efficiency. The X-ray crystal structures of three different bromodomains (CREBBP, BAZ2B, and BRPF1b) in complex with acetyl indole derivatives reveal the influence of the gatekeeper residue on the orientation of small-molecule ligands in the acetyl lysine binding site.

A facile preparation of 3-alkylindoles via Wittig reaction of 1-acetylindol-3(2H)-ones with stabilized phosphonium ylides

3-Alkylindoles can be conveniently prepared by the Wittig reaction of 1-acetyl-indol-3(2H)-ones with the stabilized phosphonium ylides.