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Design, Synthesis and Antibacterial Evaluation of 3-Substituted Ocotillol-Type Derivatives

By Kai-Yi Wang, Zhi-Wen Zhou, Heng-Yuan Zhang, Yu-Cheng Cao, Jin-Yi Xu, Cong Ma, Qing-Guo Meng and Yi Bi


Antibiotic resistance has become a serious global problem that threatens public health. In our previous work, we found that ocotillol-type triterpenoid saponin showed good antibacterial activity. Based on preliminary structure-activity relationship, novel serious C-3 substituted ocotillol-type derivatives <b>7</b>–<b>26</b> were designed and synthesized. The in vitro antibacterial activity was tested on five bacterial strains (<i>B. subtilis</i> 168, <i>S. aureus</i> RN4220, <i>E. coli</i> DH5α, <i>A. baum</i> ATCC19606 and MRSA USA300) and compared with the tests on contrast. Among these derivatives, C-3 position free hydroxyl substituted compounds <b>7</b>–<b>14</b>, showed good antibacterial activity against Gram-positive bacteria. Furthermore, compound <b>22</b> exhibited excellent antibacterial activity with minimum inhibitory concentrations (MIC) values of 2 μg/mL against MRSA USA300 and 4 μg/mL against <i>B. subtilis</i>. The structure-activity relationships of all current ocotillol-type derivatives our team synthesised were summarized. In addition, the prediction of absorption, distribution, metabolism, and excretion (ADME) properties and the study of pharmacophores were also conducted. These results can provide a guide to further design and synthesis works

Topics: triterpenoid saponin, ocotillol, antibacterial activity, synthesis, structure-activity relationship, Organic chemistry, QD241-441
Publisher: MDPI AG
Year: 2018
DOI identifier: 10.3390/molecules23123320
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