2. Academic Validation
  3. Activated carbon/Brønsted acid-promoted aerobic benzylic oxidation under "on-water" condition: Green and efficient synthesis of 3-benzoylquinoxalinones as potent tubulin inhibitors

Activated carbon/Brønsted acid-promoted aerobic benzylic oxidation under "on-water" condition: Green and efficient synthesis of 3-benzoylquinoxalinones as potent tubulin inhibitors

  • Eur J Med Chem. 2020 Jan 15:186:111894. doi: 10.1016/j.ejmech.2019.111894.
Qi Guan 1,  Lin Cong 2,  Qing Wang 3,  Changyue Yu 2,  Kai Bao 3,  Kai Zhou 4,  Lan Wu 5,  Weige Zhang 6
Affiliations

Affiliations

  • 1 Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang 110016, China; Department of Pharmacology, Northeast Pharmaceutical Group Co.,Ltd., 8 Kunming Lake Street, Economic-Technological Development Area, Shenyang, 110027, China.
  • 2 Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang 110016, China.
  • 3 School of Wuya, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang, 110016, China.
  • 4 Department of Pharmacology, Northeast Pharmaceutical Group Co.,Ltd., 8 Kunming Lake Street, Economic-Technological Development Area, Shenyang, 110027, China.
  • 5 Department of Geratology, The First Affiliated Hospital, China Medical University, 155 Nanjing North Street, Heping District, Shenyang, 110001, China.
  • 6 Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang 110016, China. Electronic address: zhangweige2000@sina.com.
PMID: 31787361 DOI: 10.1016/j.ejmech.2019.111894
Abstract

Green chemistry is becoming the favored approach to preparing drug molecules in pharmaceutical industry. Herein, we developed a clean and efficient method to synthesize 3-benzoylquinoxalines via activated carbon promoted aerobic benzylic oxidation under "on-water" condition. Moreover, biological studies with this class of compounds reveal an antiproliferative profile. Further structure modifications are performed and the investigations exhibited that the most active 12a could inhibit the microtubule polymerization by binding to tubulin and thus induce multipolar mitosis, G2/M phase arrest, and Apoptosis of Cancer cells. In addition, molecular docking studies allow the rationalization of the pharmacodynamic properties observed. Our systematic studies provide not only guidance for applications of O2/AC/H2O system, but also a new scaffold targeting tubulin for antitumor agent discovery.

Keywords

3-Benzoylquinoxalinone; Green chemistry; Molecular modelling; On-water; Tubulin inhibitor.

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