1954-45-6

Usage

Uses

Used in Pharmaceutical Industry:
4-METHYL-DL-TRYPTOPHAN is used as a key intermediate in the preparation of Indolocarbazoles and related compounds, which are known as AP-70 kinase inhibitors. These inhibitors play a crucial role in the development of new drugs targeting specific kinases involved in various diseases, including cancer and other disorders.
In the synthesis of Indolocarbazoles, 4-METHYL-DL-TRYPTOPHAN provides a stable and versatile starting material, enabling the creation of novel and effective therapeutic agents. Its chemical properties allow for the formation of a wide range of derivatives, making it a valuable component in the advancement of pharmaceutical research and drug development.

InChI:InChI=1/C12H14N2O2/c1-7-3-2-4-10-11(7)8(6-14-10)5-9(13)12(15)16/h2-4,6,9,14H,5,13H2,1H3,(H,15,16)

Upstream product

• 16096-32-5 4-methyl-1H-indole 
• 302-84-1 serin 
• 164119-81-7 N,N-dimethyl-1-(4-methyl-1H-indol-3-yl)methanamine 
• 164119-68-0 acetylamino-(4-methyl-indol-3-ylmethyl)-malonic acid diethyl ester 
• 6639-59-4 N-(2,3-dimethylphenyl)formamide 

Downstream Products

• 33468-33-6 (R)-2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid 

Relevant academic research and scientific papers

Synthesis method of indole monosubstituted 2-hydroxy-3-(1H-indole-3-yl) propionic acid compound

The invention relates to a synthesis method of an indole monosubstituted 2-hydroxy-3-(1H-indole-3-yl) propionic acid compound, which comprises the following steps of (1) reacting a compound shown as aformula I, DL-serine and acetic anhydride in the presence of a solvent under the protection of inert gas, removing the solvent, and carrying out heat treatment under alkaline conditions to obtain a compound shown as a formula II, (2) under the protection of inert gas, enabling the compound shown in a formula II to react in the presence of nitrite, H2SO4 and water to prepare a compound shown in aformula III, the structural formula of the compound in the formula I being shown in the specification, the structural formula of the compound in the formula II being shown in the specification, the structural formula of the compound in the formula III being shown in the specifications, and in the formulas I, II and III, R being one of alkyl, alkoxy and halogen. Monosubstituted indole and serine are used as raw materials, the indole monosubstituted 2-hydroxy-3-(1H-indole-3-yl) propionic acid compound is prepared through a chemical synthesis method, the raw materials are easy to obtain and cheap, operation is easy, few steps are needed, and the product yield is high.

Synthesis of enantiomerically pure 4-alkylsubstituted tryptophan derivatives by a combination of organometallic reactions with enantioselective enzymatic transformations

The synthesis of enantiomerically pure 4-substituted tryptophans 12 is described. Key steps are i) the introduction of an alkyl substituent into the 4-position of the indole via regioselective lithiation of N-TIPS protected gramine and ii) the enantioselective saponification of the phenyl acetamides of 4-substituted tryptophans by the enzyme penicillin G acylase.