Description
7-Azaindole is the starting material for the synthesis of azaserotonin. Its derivatives are of great value in drug development, for example, as the backbone of protein kinase B (PKB/Akt) inhibitors. 7-Azaindole and its derivatives have a variety of biological activities, for example, 7-azatryptophan is able to inhibit the growth of tobacco and carrot cells. In addition, it also binds to the Erm enzyme (methyltransferase family), thereby conferring antibiotic resistance.
Chemical Properties
Brown-Cyrstalline Solid
Uses
7-Azaindole is imidazolinone derivatives as CGRP receptor antagonists used in the treatment.
A heterocyclic molecule that can be utilized as a pharmaceutical building block.
Starting material in a recent synthesis of azaserotonin.
Application
7-Azaindole is a heterocyclic organic compound, which is an organic synthesis intermediate and a pharmaceutical intermediate. It is the core structure of many drugs, such as antitumor drugs, dopamine D4 receptors, p38 kinase inhibitors, thrombin inhibitors, etc.
Preparation
Synthesis of 7-azaindole: in a single-necked flask, add 2.0 g of 2-amino-3-methylpyridine and 2.5 g of N-Methylformanilide into 40 mL of dichloromethane, and add 3.15 g of PCl with stirring under an ice-water bath. After 4 hours of reaction, the reaction system was slowly poured into 40 mL of ammonia water, and the insoluble matter was removed by suction filtration. The organic layer was separated, washed twice with water, dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 2.91 g of 7-azaindole as a pale yellow solid, with a yield of 70%.
Definition
ChEBI: 1H-pyrrolo[2,3-b]pyridine is a pyrrolopyridine.
Purification Methods
Recrystallise it repeatedly from EtOH, then sublime it in a vacuum [Tokumura et al. J Am Chem Soc 109 1346 1987]. The N-acetate has m 65-66o (from *C6H6), and the picrate has m 232-233o (from Me2CO) [Clemo & Swan J Chem Soc 603 1945, Beilstein 23 III/IV 1105.]
