2. Academic Validation
  3. Synthesis of thioether andrographolide derivatives and their inhibitory effect against cancer cells

Synthesis of thioether andrographolide derivatives and their inhibitory effect against cancer cells

  • Medchemcomm. 2017 Apr 28;8(6):1268-1274. doi: 10.1039/c7md00169j.
Yi Liu 1,  Ren-Ming Liang 1,  Qing-Ping Ma 1,  Kai Xu 1,  Xin-Yong Liang 1,  Wei Huang 2 3,  Robert Sutton 3,  Jie Ding 1,  Paul M O'Neil 3,  Chun-Ru Cheng 1 3 4
Affiliations

Affiliations

  • 1 School of Chemical Engineering , Institute of Pharmaceutical Engineering Technology and Application , Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education , Sichuan University of Science & Engineering , Xueyuan Street 180, Huixing Road , Zigong , Sichuan 643000 , People's Republic of China . Email: dingjie@suse.edu.com ; Email: pharmaceutics@163.com ; Tel: +86 813 5505601.
  • 2 Department of Integrated Traditional Chinese and Western Medicine , Sichuan Provincial Pancreatitis Center , West China Hospital , Sichuan University , Chengdu , Sichuan , 643204 China.
  • 3 Department of Molecular and Clinical Cancer Medicine , Institute of Translational Medicine , University of Liverpool , Prescot Street , Liverpool L69 8XP , UK.
  • 4 Department of Chemistry , University of Liverpool , Crown Street , Liverpool L69 7ZD , UK.
PMID: 30108837 DOI: 10.1039/c7md00169j
Abstract

A series of novel thioether andrographolide derivatives were synthesized by incorporating various aromatic (or heteroaromatic) substituents into C-12 or 14-OH. A total of 38 andrographolide derivatives were prepared and evaluated for their in vitro inhibitory activity against Cancer cells. All the derivatives exhibited better activity against prostate Cancer cells (PC-3) than the parent compound. Among these, compounds 6a, 8, 9, 17, 19, 31, and 32 demonstrated good activity. These compounds were further evaluated for their Anticancer activities against other Cancer cell lines including MCF-7, MDA-MB-231, and A549. Compounds 31 and 32 showed excellent activity against MCF-7 with an IC50 value of 0.7 and 0.6 μM, respectively. The absolute configuration of 15a was determined via single-crystal X-ray diffraction. The activity of 6a (12S), which was the precursor of 15a, was better than that of the diastereoisomer 6b (12R). Moreover, the preliminary structure-activity relationship has been summarized. The results obtained herein are very important for further optimization of andrographolide.

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