Efficient synthesis and cell migration inhibitory effect of substituted benzamidothiazolylpyrazole-capped AWD*I-NH2

Mian Yang, Jun Chen, Wancai Peng, Qiqi Li, Hui Shao, Guanping Tang, Tong Cun Zhang, Yoshikazhu Takada, Long Ye, Xing Hua Liao

Research output: Contribution to journalArticlepeer-review


Substituted (2-benzamidothiazol-5-yl)pyrazole-capped AWD*I-NH2 were synthesized and their antimigration activity was studied. The improved efficiency and scalability of the analog synthesis was achieved via a late-stage diversification of the benzoyl group and a convergent route in which the bisazole capping agents and off-resin peptide AWD*I-NH2 were prepared in parallel and coupled together in solution at the last step. Bioassay results indicate that all the peptidomimetics can significantly inhibit the migration of breast cancer cells MDA-MB-231 but possess no apparent cytotoxicity. In general, the antimigration potency of the peptidomimetics is correlated to the electron-withdrawing capacity of the substituents on the terminal phenyl ring. The inhibitory effect shows dose-dependent and holds also against lung and cervical cancer cells. The level of f-actin was reduced dramatically in cells treated with the inhibitor, suggesting that the migration inhibitory effect is related to the disruption of cell locomotive protrusions.

Original languageEnglish (US)
Article number126914
JournalBioorganic and Medicinal Chemistry Letters
Issue number4
StatePublished - Feb 15 2020


  • Cell migration
  • f-Actin
  • Inhibition
  • Peptidomimetics
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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