33025-60-4

Basic information

• Product Name: N-Acetyl-3-hydroxyindole
• Synonyms: 1-acetyl-1h-indol-3-o;N-ACETYL-3-HYDROXYINDOLE;N-ACETYL-3-INDOLOL;1-ACETYLINDOL-3-OL;1-ACETYL-3-HYDROXYINDOLE;N-ACETYLINDOL-3-OL;N-Indoxyl Acetate;1-(3-Hydroxyindol-1-yl)ethanone
• CAS NO: 33025-60-4
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Product Categories: Indoles and derivatives;Indole Derivatives;Intermediates
• Mol File: 33025-60-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 140-142°C
• Boiling Point: 332.698 °C at 760 mmHg
• Flash Point: 155.011 °C
• Appearance: Off-white crystals
• Density: 1.243 g/cm³
• Vapor Pressure: 7.42E-05mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Refrigerator
• Solubility: Acetone, Chloroform (Slightly), Ethyl Acetate, Methanol (Slightly)
• PKA: 9.32±0.40(Predicted)
• CAS DataBase Reference: N-Acetyl-3-hydroxyindole(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-3-hydroxyindole(33025-60-4)
• EPA Substance Registry System: N-Acetyl-3-hydroxyindole(33025-60-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 33025-60-4(Hazardous Substances Data)

Usage

Description

N-Acetyl-3-hydroxyindole is an organic compound that serves as a valuable synthetic intermediate in various chemical reactions and processes. It is characterized by its unique molecular structure, which features an indole ring with a hydroxyl group and an acetyl group attached to the nitrogen atom. N-Acetyl-3-hydroxyindole is known for its auxin-like properties, making it a versatile building block in the synthesis of peptidomimetics and other bioactive molecules.

Uses

Used in Pharmaceutical Industry:
N-Acetyl-3-hydroxyindole is used as a synthetic intermediate for the preparation of peptidomimetics, which are peptide-like compounds designed to mimic the structure and function of natural peptides. These peptidomimetics have potential applications in drug discovery and development, as they can exhibit improved stability, bioavailability, and selectivity compared to their natural counterparts.
Used in Agrochemical Industry:
Due to its auxin-like properties, N-Acetyl-3-hydroxyindole can be used in the development of plant growth regulators and other agrochemicals. These compounds can help promote plant growth, improve crop yields, and enhance resistance to various environmental stresses.

InChI:InChI=1/C10H9NO2/c1-7(12)11-6-10(13)8-4-2-3-5-9(8)11/h2-6,13H,1H3

Upstream product

• 16800-67-2 N,O-diacetylindoxyl 
• 480-93-3 indoxyl 
• 108-24-7 acetic anhydride 
• 16851-69-7 2-(N-(carboxymethyl)acetamido)benzoic acid 
• 612-42-0 phenylglycine-o-carboxylic acid 
• 118-92-3 anthranilic acid 

Downstream Products

• 7497-97-4 (1-acetyl-indol-3-yl)-(tetra-O-acetyl-β-D-glucopyranoside) 
• 38073-42-6 (2Z)-2-(phenylmethylidene)-2,3-dihydro-1H-indol-3-one 
• 698397-47-6 C₁₆H₁₃BrN₂O 
• 67766-00-1 N-acetyl-3-p-nitrophenylaminoindole 
• 1148119-21-4 (Z)-2-(3-hydroxy-4-methoxybenzylidene)indolin-3-one 
• 658041-31-7 4-((1-acetyl-1H-indol-3-yl)amino)benzonitrile 

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.

CYCLIC AMIDE DERIVATIVES AS INHIBITORS OF 11 - BETA - HYDROXYSTEROID DEHYDROGENASE AND USES THEREOF

The present invention relates to certain amide derivatives that have the ability to inhibit 11-β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1) and which are therefore useful in the treatment of certain disorders that can be prevented or treated by inhibition of this enzyme. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders. It is expected that the compounds of the invention will find application in the treatment of conditions such as non-insulin dependent type 2 diabetes mellitus (NIDDM), insulin resistance, obesity, impaired fasting glucose, impaired glucose tolerance, lipid disorders such as dyslipidemia, hypertension and as well as other diseases and conditions.

N-ARYLALKYL-3-AMINOALKOXYINDOLES AND THEIR USE AS 5-HT LIGANDS

The present invention describes substituted 3-Aminoalkoxyindoles, as compounds of the general formula (I), its stereoisomers, its radioisotopes, its geometric forms, its N-oxides, its polymorphs, its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates, its useful bioactive metabolites and any suitable combination of the above. The invention also discloses the processes for preparing such compounds of the general formula (I), its stereoisomers, its radioisotopes, its geometric forms, its N-oxides, its polymorphs, its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates, its useful bio-active metabolites and also includes any suitable combination of the above. Further described are various methods of administering these compounds of general formula (I), i.e. pharmaceutically acceptable dosage forms, their composition and their use in either therapy or diagnosis.