27866-52-0

Upstream product

• 13754-86-4 1,5,6,7-tetrahydro-indol-4-one 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 

Downstream Products

• 27866-53-1 5-bromo-4-oxo-N-benzoyl-4,5,6,7-tetrahydroindole 
• 95969-15-6 (4-Hydroxy-indol-1-yl)-phenyl-methanone 

Relevant academic research and scientific papers

4-hydroxyindole preparation method suitable for industrial production

The invention relates to the technical field of organic synthesis, in particular to a preparation method of a medical intermediate 4-hydroxyindole. The method includes: taking 1, 5, 6, 7-tetrahydro-4H-indole-4-one as the raw material, carrying out nucleophilic substitution reaction under the action of alkali to obtain an amino protection product (I), reacting the compound (I) with a halogenation reagent to obtain alpha-halogenated ketone (II), subjecting the compound (II) to elimination reaction under the action of alkali to remove HX so as to obtain a 4-hydroxyindole derivative (III), and finally conducting hydrolysis deprotection on the compound (III) to obtain 4-hydroxyindole (IV). The invention provides a simple industrial production route for 4-hydroxyindole, and the method has the advantages of simple reaction operation, avoidance of high temperature, high pressure and catalytic reaction, and low cost.

Development of 4,5-dihydro-benzodiazepinone derivatives as a new chemical series of BRD4 inhibitors

Bromodomains (BRDs) are protein interaction modules that selectively recognize ?-N-lysine residues, serving as key epigenetic readers and play a key role in epigenetic regulation of gene transcription. Bromodomain-containing protein 4 (BRD4), a protein containing two BRDs termed BD1 and BD2, has emerged as an attractive candidate for the development of inhibitors targeting gene transcription in several types of cancers. In this study, we made structural modifications of previously reported BRD4 inhibitors, to develop new chemical scaffold 3,4-dihydroquinoxalin-2(1H)-one. Four series of compounds (compounds 7e10) were synthesized, and the BRD4-inhibitory activity and anti-proliferative effect of these compounds were evaluated. We found compound 10d has remarkable anti-proliferative activities toward leukemia cells and could induce apoptosis by mitochondrial pathways. Notably, the analysis of molecular docking suggested that hydrophobic interaction was essential for compound 10d to bind to BD1. In conclusion, these results demonstrate the potential of compound 10d to be utilized as a BRD4 inhibitor with apoptosis inducing effect in future leukemia therapy.

Synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoester

Pd(OAc)2-catalyzed decomposition of ethyl 2-diazo-4-(4-indolyl)-3- oxobutanoate leads to a tricyclic tetrahydrobenzindole compound formed by a formal C-H insertion reaction. This tricyclic indole rearranges to a novel and thermodynamically more stable nap