Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China.
Chinese Academy of Sciences Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences, Shanghai, China.
Org Biomol Chem. 2021 Apr 28;19(16):3589-3594. doi: 10.1039/d1ob00296a.
Inspired by aspirin and chalcone, herein, we describe a modular biomimetic strategy to achieve a new class of CF3-bearing benzannulated macrolactams. The key to the success of macrolactams was the utilization of a highly chemoselective Rh(iii)-catalyzed native carboxylic acid-directed C-H alkylation. Moreover, the unique CF3-containing benzannulated macrocycles showed decent immunosuppressive effects on B cells in vitro, including proliferation, activation, and antibody production upon specific stimulation implicating TLR and BCR signaling.
受阿司匹林和查耳酮的启发，本文描述了一种模块化仿生策略，以实现一类新的含三氟甲基的苯并稠合大环内酯。大环内酯成功的关键是利用高度选择性的 Rh(iii)催化的天然羧酸导向的 C-H 烷基化反应。此外，独特的含三氟甲基的苯并稠合大环化合物在体外对 B 细胞表现出相当的免疫抑制作用，包括在特定刺激下 TLR 和 BCR 信号转导引起的增殖、激活和抗体产生。
