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Medicinal chemistry and drug research require diverse chemical components to meet strict requirements not only in terms of physical and chemical properties but also in terms of chemical reactivity.
The chemists use the 'build–couple–pair' strategy of organic synthesis, which entails preparing molecular building blocks that contain several chemical groups.
The chemical building block (CBB) is a molecule which can be converted to various secondary chemicals and intermediates, and, in turn, into a broad range of different downstream uses.
Benzopyrans are the core structures of compounds widely existing in scientific fields, including pharmaceutical chemistry, physical chemistry, synthetic organic chemistry and natural product chemistry. At the same time, it is a kind of heterocyclic compound with drug activity. In the past few decades, benzopyran and its derivatives have played an important role in the bioactive compounds. It has anti-virus, anti-bacterial, anti-oxidation, anticoagulant, anti-cancer and other activities. It can be used as anticoagulant, antifungal, antidegradant, estrogen, antituberculosis, herbicide and so on. The key factor is that benzopyran and its derivatives are lipophilic and can easily penetrate the cell membrane. The following figure shows the structural formula of benzopyran with antibacterial activity:
The structure-activity relationship of benzopyranone showed that when the skeleton of benzopyranone was replaced by sulfur or oxygen atoms, the antitumor activity of benzopyranone was improved. It was found that benzopyrans can inhibit the peroxidation of liver homogenate and the oxidation of LDL induced by FeCl2 · ADP or ccl4-nadph in vitro, and can alleviate the injury of vascular endothelial cells induced by oxidized LDL and lysophosphatidylcholine. In addition, some researchers have synthesized benzopyrans and found that they have good antibacterial activity against plant pathogens. The chromone ring system of benzopyran exists in some natural products, such as α - tocopherol, a powerful antioxidant, which can prevent cancer, cataract and coronary artery disease, heart disease. Compounds with antioxidant activity and scavenging effect play an important role in oxidative stress response and prevention of some chronic degenerative diseases. Even benzopyrans can be used as activators of PPAR γ.
Small molecule organogels can be widely used in drug delivery, chemical sensors, tissue engineering, biomimetic systems, photoelectric devices and so on. Benzopirone is a derivative of benzopiran. It can form an inner ring compound by binding with Schiff base compound. The researchers combine it with Schiff base compound to get the organic gel factor G1, which has high sensitivity and selectivity to Fe3+. It is stable in many neutral solutions and can effectively respond to illumination, heating, physical shock and other stimuli.
Benzopyrans have been widely used in the field of fluorescent probes, among which coumarin is the dominant one. Fluorescent probes play an important role in metal ion recognition and biological system detection. Some researchers combined benzopyran derivatives, such as 2-phenyl-2h-benzopyranolaldehyde, with pyrazoline fluorescent probes. The results showed better cell permeability, enhanced selectivity, increased sensitivity and lower cytotoxicity.