116524-14-2

Upstream product

• 244205-40-1 (2-bromophenyl)boronic acid 
• 13534-90-2 dibromo-3,4 pyridine 
• 1312012-36-4 3-bromo-4-(2-bromophenyl)pyridine 
• 100-46-9 benzylamine 
• 244-63-3 betacarboline 
• 100-44-7 benzyl chloride 

Downstream Products

• 244-63-3 betacarboline 

Relevant academic research and scientific papers

Copper-Catalyzed Synthesis of β- And δ-Carbolines by Double N-Arylation of Primary Amines

Two efficient and practical approaches are reported for the synthesis of β- and δ-carbolines from 3,4-dibromopyridine. The synthesis is based on site-selective Cu-catalyzed double C-N coupling reactions and subsequent annulations by twofold Pd-catalyzed C-N coupling with amines.

Efficient access to β- and γ-carbolines from a common starting material by sequential site-selective Pd-catalyzed C–C, C–N coupling reactions

Two efficient and practical approaches are reported for the synthesis of β- and γ-carboline derivatives from 3,4-dibromopyridine as a common starting material. The β-carbolines were prepared by site-selective Pd-catalyzed C–C coupling with o-bromophenylboronic acid and subsequent cyclization by double C–N coupling with amines. γ-Carbolines were prepared from the same starting material by C–N coupling with anilines and subsequent annulation by domino C–C/C–N coupling with o-bromophenylboronic acid.

Synthesis and structure-activity relationships of N2-alkylated quaternary β-carbolines as novel antitumor agents

A series of novel N2-alkylated quaternary β-carbolines was synthesized by modification of position-1, 2, 7 and 9 of β-carboline nucleus with various alkyl and arylated alkyl substituents, and their cytotoxic activities in vitro and antitumor potencies in mice were evaluated. Compound 3m was found to be the most potent antitumor agent. SARs analysis revealed that (1) the substituents in position-2 and 9 of β-carboline nucleus played a vital role in modulation of antitumor activity; (2) the benzyl and 3-phenylpropyl substituents in position-2 and 9 of β-carboline ring were the optimal substituents giving rise to significant antitumor agent. These compounds might be a novel promising class of antitumor agents with clinical development potential.

HARMINE DERIVATIVES, INTERMEDIATES USED IN THEIR PREPARATION, PREPARATION PROCESSES AND USE THEREOF

This invention relates to compounds of general formula (I), wherein R1, R2, R3, R4 and R5 are as defined specification; intermediates used in their preparation, preparation processes and use thereof. The present invention produce harmine derivatives with enhanced antihumour activity and lower nervous system toxicity by structurally modification parent structure of β-carboline of harmines at position 1, 2, 3, 7 and 9, The compounds of the present invention can be pre easily with high yield. They can be used in manufacture of a variety of antitumour medicines and medicines used in treatm tumour diseases in combination of light or radiation therapy.

Synthetic studies on indoles and related compounds. XXVI. The debenzylation of protected indole nitrogen with aluminum chloride. (2)

A new debenzylation method using aluminum chloride in benzene or anisole, which had been developed by us for N-benzyl-2-acyl- and -2-ethoxycarbonylindoles, was applied to benzyl derivatives of other types of indoles and related compounds. Among them, N-benzyl derivatives of fully aromatized indoles, carbazoles and β-carbolines, and some benzamides were debenzylated successfully, whereas those of oxindoles and heterocyclic amides were not. As to the effect of a p-substituent on the benzyl group, it was found that an electron-donating substituent accelerates deprotection, whereas an electron-attracting substituent delays or prevents deprotection.