Pyridine is a six-membered heterocyclic compound containing one nitrogen heteroatom. Pyridine and piperidine are the most frequently occurring heterocyclic building blocks in drug molecules. According to incomplete statistics, there are currently more than 180 drugs containing pyridine or piperidine structure that have been marketed, nearly 1/5 of the drugs approved for marketing in recent years contain these two structures.
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Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell.
Incorporation of heterocycles into drug molecules can enhance physical properties and biological activity. Oxadiazoles are a class of five-membered heterocycles containing one oxygen and two nitrogen atoms with special biological activity and thermodynamic properties. 1,2,4- and 1,3,4-oxadiazoles are widely used in the development of bioactive molecules, but 1,2,5-oxadiazoles (furazans) are used relatively sparingly. Compared with 1,2,4- and 1,3,4-isomers, 1,2,5-oxadiazole has unique physicochemical properties and electronic effects. The furazan ring has a strong inductive effect, comparable to that of trifluoromethyl or tetrazolyl. The unique properties of furoxan can confer specific pharmacological activities to drug-like molecules.
With four imidazopyridine-containing drugs and one pyrazolopyridine-containing drug on the market, bicyclic pyridines containing ring-junction nitrogen are privileged structures in medicinal chemistry. With two nitrogen atoms with potential to serve as hydrogen bond acceptors, imidazopyridines and pyrazolopyridines may boost binding to target proteins and elevate potency. In addition, these structures have found utility in FBDD, covalent inhibitors, reducing metabolic liabilities, and creating novel chemical space and intellectual properties. With many of the advanced intermediates now commercially available, they will find more and more applications in drug discovery.
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