University Chemistry ›› 2024, Vol. 39 ›› Issue (6): 342-349.doi: 10.3866/PKU.DXHX202311070

Special Issue:

• Chemistry Laboratory • Previous Articles     Next Articles

One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation

Bingliang Li1, Yuying Han1, Dianyang Li1, Dandan Liu1,2, Wenbin Shang1,2   

  1. 1 School of Pharmaceutical Sciences and Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming 650500, China;
    2 College of Modern Biomedical Industry, Kunming Medical University, Kunming 650500, China
  • Received:2023-11-21 Revised:2024-01-05 Published:2024-06-07
  • Contact: Dandan Liu, Wenbin Shang E-mail:liudandan@kmmu.edu.cn;shangwenbin@kmmu.edu.cn

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Abstract: The current synthesis of benorilate typically involves the Schotten-Baumann esterification, which generates harmful gases HCl and SO2 from the reagent SOCl2, posing environmental concerns. Moreover, the process entails multiple steps. In this study, we have optimized a one-step method using EDCI/4-DMAP esterification for the synthesis of benorilate. The product’s structure and purity were characterized through melting point determination, NMR, and HPLC-MS analysis, followed by in vivo dynamic evaluation in rats based on plasma and bile samples. This evaluation confirmed the principles of drug design. The improved method not only enhances efficiency but also significantly improves experimental safety.

Key words: Benorilate, One-step synthesis, EDCI, In vivo analysis, Combination principles