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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 12: 3532 - 3541

DOI: https://doi.org/10.6023/cjoc201905029

Synthesis, Characteristics and Bioactivities of Novel Isosteviol Derivatives

  • Guo Yongtai ,
  • Hou Xiyan ,
  • Zheng Changji ,
  • Zhao Chunhui ,
  • Jin Yuting ,
  • Gao Xueqin ,
  • Wang Qian ,
  • Sun Lei ,
  • Zhao Longxuan ,
  • Piao Hua
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  • a School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029;
    b College of Life Science, Dalian Nationalities University, Dalian, Liaoning 116600;
    c College of Pharmacy, Yanbian University, Yanji, Jilin 133002;
    d Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Liaoning Normal University, Dalian, Liaoning 116029;
    e Department of Physiology, College of Basic Medical Sciences, Dalian Medical University, Dalian, Liaoning 116044

Received date: 2019-05-13

  Revised date: 2019-06-26

  Online published: 2019-08-01

Supported by

Project supported by the National Natural Science Foundation of China (No. 21101067).

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Abstract

Fifteen novel isosteviol derivatives were designed and synthesized by introducing morpholine and piperazine moieties into C-16 and C-19 position through connecting fragments, and the D-ring structure was modified. The inhibitory effects on Colo-16 and A549 were observed, the results showed that the inhibitory activities of 4 compounds on Colo-16 were significantly better than the positive control of 5-fluorouracil. The inhibitory effects on E. coli 1924, S. aureus 4220, S. mutans 3289, MRSA 3167 and QRSA 3505 were also observed, the results showed that the minimum inhibitory concentration (MIC) of 6 compounds on S. mutans 3289 was 8 μg/mL, which was comparable to the positive control chloramphenicol. The MIC of 16β-O-(5-oxo-5-(4-methyl-1-piperazinyl)-valeryl)]-19-beyeran acid ethyl ester (IS-12b) on MRSA 3167 was 8 μg/mL, which was comparable to the positive control chloramphenicol.

Key words： isosteviol; cytotoxic activity; antibacterial activity

Cite this article

Guo Yongtai , Hou Xiyan , Zheng Changji , Zhao Chunhui , Jin Yuting , Gao Xueqin , Wang Qian , Sun Lei , Zhao Longxuan , Piao Hua . Synthesis, Characteristics and Bioactivities of Novel Isosteviol Derivatives[J]. Chinese Journal of Organic Chemistry, 2019 , 39(12) : 3532 -3541 . DOI: 10.6023/cjoc201905029

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