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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Cyclohexane is an organic compound with a chemical formula C6H12. It is a colorless liquid with a pungent odor, insoluble in water, and soluble in most organic solvents such as ethanol, ether, benzene, and acetone. Cyclohexyl fragments are a common structure in both natural and synthetic drugs. It can be used as both core structure and part of achiral side chain.
Oxygen heterocycles are one of the most common heterocycles in drugs and natural products. Oxetene has high polarity and is also a good acceptor for hydrogen bond, which contributes to the metabolism and chemical stability of its host molecules. When substituted for commonly used functional groups such as gem dimethyl or carbonyl, oxetane units can induce profound changes in water solubility, lipophilicity, metabolic stability and conformational preference. Four of the FDA-approved drugs contain oxetenes: Orlistat, Paclitaxel, and two of its derivatives, Docetaxel and Cabazitaxel. Currently, oxetane-containing building blocks are flourishing in medicinal chemistry and drug discovery.