Quinazolines

Quinazolines are a class of heterocyclic aromatic organic compounds. The core structure consists of a benzene ring fused to a pyrimidine ring. This bicyclic system, known as quinazoline, has the chemical formula C8H6N2. The numbering of the quinazoline ring starts from one of the nitrogen atoms and proceeds around the fused system. Quinazolines are isomers of other fused bicyclic heterocycles, such as quinolines and isoquinolines, which differ in the position of the nitrogen atoms within the fused ring system.

The quinazoline scaffold is a privileged structure in medicinal chemistry, meaning it is frequently found in biologically active molecules. Many derivatives of quinazoline exhibit a wide range of pharmacological properties, including anticancer, antimicrobial, anti-inflammatory, analgesic, and antihypertensive activities. These diverse biological effects arise from the ability of the quinazoline core to interact with various biological targets, such as enzymes and receptors.

Numerous synthetic routes have been developed for the preparation of quinazoline derivatives. These methods often involve cyclization reactions starting from substituted anilines or anthranilic acids. The functionalization of the quinazoline ring allows for the fine-tuning of its physical and biological properties, leading to the discovery and development of new therapeutic agents. For example, gefitinib and erlotinib are well-known quinazoline-based drugs used in the treatment of certain types of lung cancer.