Indoline is an aromatic heterocyclic organic compound with the chemical formula C8H9N. The compound is based on the indole structure, but the 2-3 bond is saturated. Indoles and their derivatives continue to inspire the development of synthetic organic chemistry even years after their discovery. The specific scaffold is a privileged structure and is ubiquitous in pharmaceuticals and biologically active compounds. Fused indolines as indole derivatives are of particular interest as they are often found in natural products and bioactives such as strychnine and tryptanthrins (alkaloids), mitosanes and mitosenes (antitumor activity) and isatisine (antiviral activity).
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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