Progress in Synthesis and Bioactivity of Spiroisoxazoline Compounds

Abstract

Spiroisoxazoline compounds have so extensive biological activity that they are important drug intermediates, and they are also important organic synthetic intermediates. The relevant reports for forty years are reviewed in this paper. On the basis of reaction mechanisms, the synthetic methods of spiroisoxazoline compounds are classified into the following five types: oxidation, intramolecular condensation, nucleophilic addition, 1,3-dipolar cycloaddition, and other methods. Among them, the most widely used method is 1,3-dipolar cycloadditio. This method is of simple operation, high yield and good stereoselectivity, but one of its synthons-carbon dipolarophiles is not easy to get, and generally goes through many steps of reaction to prepare. In addition, their biological activities are summarized as six categories: the activity of inhibiting the growth of the larvae, the activity of slowing hardening of the arteries, the activity for the treatment of pain, the activity of lowering blood sugar, the anticancer activity and the antibacterial activity.

Palladium-Catalyzed Ring-Forming Alkene Aminoaroylation of Unsaturated Hydrazones and Sulfonamides

“…On the basis of this mechanistic scenario, we are proposing to alter the outcome of the subsequent reaction profile of the initially formed alkyl Pd II complex by incorporation of CO-based carbonylation using unsaturated hydrazones and sulfonamides as substrates . The achievement of this reaction mode would enable ring-forming alkene aminoaroylation of unsaturated hydrazones and sulfonamides, thus providing a useful approach to benzoyl-substituted dihydropyrazoles and isoxazolidines (Scheme c) . To the best of our knowledge, such a transformation is still unknown.…”

Spiro Derivatives in the Discovery of New Pesticides: A Research Review

“…Spiro compounds are organic compounds in which a single atom connects at least two rings. − They possess a combination of characteristics that other organic compounds do not, such as a rigid, stable structure, spiro conjugation, and spiro superconjugation. , Unlike flat aromatic heterocyclic compounds, the inherent high saturation (Fsp3) and significant three-dimensional characteristics of spiro rings make them widely used in the fields of synthetic chemistry, materials chemistry, and supramolecular chemistry. − The water solubility and lipophilicity properties of lead molecules can be optimized to improve their development into useful drugs that are less prone to producing resistance . Spiro motifs are ubiquitous in natural products and drugs (Figure ).…”

Design, Synthesis, and Bioactivity of Spiro Derivatives Containing a Pyridine Moiety

“…1,2 However, the poor efficacy of current antiviral agents and the considerable insecticide resistance make it urgent to develop pesticides with high efficiency, low toxicity, and new mechanisms of action. 3 Unlike ordinary organic compounds, spiro compounds have special characteristics, such as a rigid structure, spiro conjugation, and spiro hyperconjugation, 4,5 offering them great potential for binding with biomolecules. 6 This binding potential can somewhat change the water solubility and lipophilicity of drug molecules, facilitating the development of optimized lead molecules into drugs and reducing resistance.…”