A spiro compound is a polycyclic compound in which two monocyclic rings share one carbon atom; the shared carbon atom is called a spiro atom. Spiro compounds have rigid structures, stable structures, and have special properties that general organic compounds do not possess, such as anomeric effect, spiro conjugation and spiro hyperconjugation. Compared with the monocyclic structure or the planar aromatic structure, the spiro structure has a larger three-dimensional structure; the heterocyclic spiro structure is also regarded as the biological isostere of some groups, which can change the drug to a certain extent. The water solubility, lipophilicity, dominant conformation and ADMET properties of the molecule make the optimized lead molecule easier to drug. Therefore, spiro compounds occupy a very important position in drug development.
Spiro And Bicyclic Compound
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Pyrrolidine, also known as tetrahydropyrrole, is a saturated five-membered heterocyclic ring, which is miscible with water. Pyrrolidine exists in many alkaloids and drug molecules, such as kappa opioids, antagonists of dopamine D4 receptors, and HIV reverse transcriptase inhibitors.
Cyclopropane is the smallest cyclic compound with unique structural features and physicochemical properties, which is widely used in the design of small molecule drugs. In drug design, it is often used to increase activity, fix conformation and improve PK and water solubility. The introduction of cyclopropyl groups into drugs can change various properties of molecules, such as improving metabolic stability; increasing biological activity; enhancing drug efficacy; limiting polypeptide conformation and slowing down its hydrolysis; reducing plasma clearance; improving drug dissociation and many more. Cyclopropane rings are widely found in marketed drugs, including cardiovascular drugs, central nervous system (CNS) drugs, anticancer drugs, autoimmune and anti-inflammatory drugs.
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