Quinazolines

Introduction

Quinazoline, also known as 1,3-benzodiazine, is an important drug intermediate that exists in the structural framework of some natural alkaloids. It was first reported by MT Bogert et al. in 1900. Subsequently, the synthesis of quinazoline compounds and various drug applications have been published. Most quinazolines have anti-cancer, anti-tuberculosis, anti-depression and other drug activities. Some quinazoline compounds, such as Prazosin, Lcotinib and Lapatinib, have been successfully synthesized and applied as the core framework of organic drug molecules.

There are two nitrogen atoms in the structure of quinazoline compounds, and there are various synthesis methods according to the different raw materials that provide the nitrogen source. The method of synthesis of quinazoline compounds is similar to that of quinoline compounds, but the main difference is that the parent ring is constructed by cyclic reaction with different raw materials. The main raw materials for the synthesis of quinazoline compounds are phenylaminobenzoic acid derivatives, benzylamine compounds and aniline compounds. The synthesis of quinazoline compounds from aniline compounds is the most studied method at present. In the process of synthesizing quinazoline compounds, there are mainly two paths: the first is to convert aniline into imine, and then to cyclize quinazoline. The second is aniline acylation to amide, and cyclization to quinazoline.

Applications

Pharmaceutical Chemistry:

Up to now, there are dozens of drugs on the market based on the basic skeleton of quinazoline or containing quinazoline groups. Quinazoline matrix compounds exhibit a wide range of biological activities. For example, they can be used as ligands and binding agents for the receptors in the nervous system, which can be used in anti-tuberculosis and anti-tumor therapy. After continuous structure modification, a large number of quinazoline compounds were synthesized as the basic skeleton of the protein kinase inhibitors, because quinazoline skeleton in many associated with tumorigenesis of protein kinase inhibitors development can be used as a generic template to modify.

Agriculture:

In addition to the application in medicine, quinazoline derivatives also play a very important role in pesticides, and can be used as fungicides, herbicides and so on. There are now efficient acaricides like fenazaquin as agricultural fungicides have been put on the market.

Lubricant Additives:

As lubricant additives, quinazolines can greatly improve the anti-wear and anti-friction properties of liquid. Studies have shown that, because of high electronegativity, small atomic radius and compact molecular structure, when quinazoline compounds adsorbed on the metal surface as lubricating oil additives, it is easy to form hydrogen bonds between molecules and enhance oil film strength, and can effectively restrain additives of sulfur, phosphorus and other active element in the excessive corrosion.

Fluorescent Material:

Quinazoline derivatives can emit visible light after absorbing visible and ultraviolet light. They have good acid and alkaline resistant. This kind of organic fluorescent compound, under ultraviolet light irradiation, has a strong fluorescence, which can be used as fluorescent ink.

References

  1. A, Gerjan De Bruin, et al. "Discovery of quinoline-based irreversible BTK inhibitors." Bioorganic & Medicinal Chemistry Letters (2020).
  2. Fadhil et al. "Synthesis, characterization, and anticancer activity of new quinazoline derivatives against MCF-7 cells. " The scientific world journal (2014).
Inquiry Basket