4560-07-0

Basic information

• Product Name: N-[2-(2-PHENYL-1H-INDOL-3-YL)ETHYL]ACETAMIDE
• Synonyms: N-[2-(2-PHENYL-1H-INDOL-3-YL)ETHYL]ACETAMIDE
• CAS NO: 4560-07-0
• Molecular Formula: C18H18N2O
• Molecular Weight: 278.35
• Mol File: 4560-07-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-[2-(2-PHENYL-1H-INDOL-3-YL)ETHYL]ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(2-PHENYL-1H-INDOL-3-YL)ETHYL]ACETAMIDE(4560-07-0)
• EPA Substance Registry System: N-[2-(2-PHENYL-1H-INDOL-3-YL)ETHYL]ACETAMIDE(4560-07-0)

Safety Data

• Hazardous Substances Data: 4560-07-0(Hazardous Substances Data)

Upstream product

• 1217-80-7 2-(2-phenyl-1H-indol-3-yl)ethylamine 
• 75-36-5 acetyl chloride 
• 24517-60-0 N-(4-oxo-4-phenylbutyl)acetamide 
• 100-63-0 phenylhydrazine 
• 108-86-1 bromobenzene 
• 1016-47-3 N-Acetyltryptamine 
• 948-65-2 2-phenyl-indole 
• 62005-48-5 N-acetylaminoacetaldehyde dimethyl acetal 
• 142-26-7 2-acetylaminoethanol 
• 591-50-4 iodobenzene 
• 700-91-4 2-phenyl-1-pyrroline 

Relevant articles and documents

Iridium-catalyzed direct synthesis of tryptamine derivatives from indoles: Exploiting N-protected β-amino alcohols as alkylating agents

The selective C3-alkylation of indoles with N-protected ethanolamines involving the "borrowing hydrogen" strategy is described. This method provides convenient and sustainable access to several tryptamine derivatives.

Synthesis of C-2 arylated tryptophan amino acids and related compounds through palladium-catalyzed C-H Activation

Tryptophan (Trp) and tryptophan derivatives are C2-arylated. A C-H activation process allows the preparation of both protected and unprotected arylated-Trp amino acids, directly from the amino acid precursor and aryl iodides. The obtained compounds are suitable for standard solid-phase peptide synthesis.

Synthesis of tryptamine derivatives via a direct, one-pot reductive alkylation of indoles

An efficient, one-pot reductive alkylation of indoles with N-protected aminoethyl acetals in the presence of TES/TFA is reported. It represents the first general method for the direct synthesis of tryptamine derivatives from indoles and nitrogen-functionalized acetals. This convergent and versatile approach employs safe and inexpensive reagents, proceeds under mild conditions, and tolerates several functional groups. The new procedure was efficiently applied to a gram-scale synthesis of both luzindole, a reference MT2-selective melatonin receptor antagonist, and melatonin.

Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles

(Chemical Equation Presented) This paper describes a phosphine-free palladium-catalyzed method for direct C-arylation of free (N-H)-indoles and pyrroles with iodo- and bromoarene donors. Employing commercially available materials, this new and operationally simple procedure provides a rapid entry to a wide range of C-arylated (N-H)-indoles including derivatives of tryptamine. In the course of this study, a profound halide effect was uncovered, affecting both the efficiency and regioselectivity of indole arylation.

Convenient synthesis of melatonin analogues: 2- and 3-substituted -N-acetylindolylalkylamines

A new method for the synthesis of 2- and 3-substituted indolylalkylamides, derivatives of melatonin, from arylhydrazines and amidoketones by the Fischer reaction was elaborated. The amidoketones can be easily prepared from cyclic imines by reaction with acylpyridinium chloride. This method is a one-step synchronous creation of the selected alkylamide fragment and the indole core. Variation of the arylhydrazines create the desired substituents in the carbocycle of indolylalkylamides and suitable choice of amidoketone can direct the amidoalkyl chain to the 2- or 3-position of the indole. Graphical Abstract

Analog binding to melatonin receptors in chick brain: Effects of GTP and prazosin

2-[125I]Iodomelatonin binding studies were carried out in chick brain membranes to compare the high-affinity melatonin receptor pharmacology of various 2-phenylmelatonin-based compounds, the naphthalenic agonist S-20098, and melatonin. Competit

Mapping the Melatonin Receptor. 3. Design and Synthesis of Melatonin Agonists and Antagonists Derived from 2-Phenyltryptamines

Three series of 2-phenyltryptamides were prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor in chicken brain and in Xenopus laevis melanophore cells.The 5-methoxy-2-phenyltryptamides (6a-j) have high bi