Design and Synthesis of Spirobiisoxazoline Derivatives

Madhuswapnaja, K. Jones; Yennam, Satyanarayana; Chavali, Murthy

doi:10.1002/9781119640929.ch6

Cited by 2 publications

(2 citation statements)

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“…[1] Studies on their (partially) saturated derivatives, such as isoxazolidines and isoxazolines, have shown promise in developing new building blocks for medicinal chemistry and exploring their biological activities. [2][3][4] The 5,5substituted 2-isoxazolines, in particular, have gained attention in drug discovery programs due to their diverse pharmacological activities. Thus, Fluralaner (Bravecto™) was approved by the FDA and the EMA in 2014 and is widely used for flea treatment in pets.…”

Section: Introductionmentioning

confidence: 99%

“…Isoxazoles are an important class of compounds in medicinal chemistry and have been found in more than 90 compounds, according to DrugBank [1] . Studies on their (partially) saturated derivatives, such as isoxazolidines and isoxazolines, have shown promise in developing new building blocks for medicinal chemistry and exploring their biological activities [2–4] . The 5,5‐substituted 2‐isoxazolines, in particular, have gained attention in drug discovery programs due to their diverse pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Spirocyclic and Fused Isoxazoline Building Blocks

et al. 2023

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A highly efficient multigram synthesis of spirocyclic and fused isoxazoline building blocks is described. Isoxazoline‐3‐carboxylates were synthesized via a regioselective 1,3‐dipolar cycloaddition reaction of 2‐chloro‐2‐(hydroxyimino)acetate and carbo‐ or heterocyclic alkenes bearing endo‐ or exocyclic C=C double bonds, resulting in fused or spirocyclic isoxazolines, respectively. The preparation of up to 300 g of these compounds was achieved in a single run. The ester group of isoxazolines was then subjected to common synthetic transformations for the synthesis of corresponding building blocks, including alcohols, chlorides, azides, amines, aldehydes, carboxylic acids, amino acids and their derivatives, difluoromethyl‐substituted compounds, and bicyclic γ‐lactones. Additionally, a direct cycloaddition‐based approach to the synthesis of aminoalkyl‐ and chloromethyl‐substituted isoxazolines was proposed to improve their preparation. The described isoxazoline building blocks are expected to be valuable tools for drug discovery.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%