Pétry Nicolas, Luttringer Florian, Bantreil Xavier, Lamaty Frédéric
IBMM, Université de Montpellier, CNRS, ENSCM, Montpellier, France.
Institut Universitaire de France (IUF), France.
Faraday Discuss. 2023 Jan 5;241(0):114-127. doi: 10.1039/d2fd00096b.
Sydnones are heterocyclic compounds which display important biological activities, including their abilities to react in 1,3-dipolar additions for applications in the development of new prodrugs. Capitalizing on our preliminary work on the mechanosynthesis of sydnones, an extension of this work to two related families of molecules, diarylsydnones and iminosydnones is reported. A ball-milling approach towards the synthesis of diaryl sydnones was developed, a necessary step for the synthesis of potential sydnone-based ligands of metal complexes. A mechanochemistry-based synthesis of iminosydnones was optimized, including the preparation of active pharmaceutical ingredients (API) related to feprosidnine, linsidomine, mesocarb and molsidomine. This work demonstrated that the ball-milling procedures were efficient and time saving through avoiding purification steps, and reduced the use of organic solvents.
斯德酮是一类杂环化合物，具有重要的生物活性，包括在1,3 -偶极加成反应中的反应能力，可用于新型前药的开发。基于我们在斯德酮机械合成方面的初步工作，本文报道了将该工作扩展至两个相关分子家族，即二芳基斯德酮和亚氨基斯德酮。开发了一种通过球磨法合成二芳基斯德酮的方法，这是合成潜在的基于斯德酮的金属配合物配体的必要步骤。优化了基于机械化学的亚氨基斯德酮合成方法，包括制备与非诺西定、林西多明、美索卡和吗多明相关的活性药物成分（API）。这项工作表明，球磨法通过避免纯化步骤，高效且省时，并减少了有机溶剂的使用。
