Scientific Reports (Dec 2022)

Diarylation of thiazolopyrimidines by laccase and their in vitro evaluation as antitumor agents

  • Mansour Shahedi,
  • Rojina Shahani,
  • Zohreh Habibi,
  • Maryam Yousefi,
  • Jesper Brask,
  • Arash Minaei-Tehrani,
  • Fatemeh Yazdi Samadi,
  • Mehdi Mohammadi

DOI
https://doi.org/10.1038/s41598-022-26820-9
Journal volume & issue
Vol. 12, no. 1
pp. 1 – 12

Abstract

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Abstract A mild and efficient method was developed for the synthesis of new derivatives of thiazolo[3,2-a] pyrimidin-3(2H)-ones from available starting materials based on the oxidation of catechols to ortho-quinone by Myceliophthora thermophila laccase (Novozym 51,003) and 1,4-addition of active methylene carbon to these in situ generated intermediates in moderate to good yields (35–93%). The structure of the products was confirmed through 1H NMR, 13C NMR, HMBC, HSQC, DEPT-135, and mass spectroscopy techniques. These novel compounds were evaluated as active antitumor agents against human colorectal adenocarcinoma and liver adenocarcinoma cell lines. All compounds displayed potent inhibition activities against the HT-29 cell line with IC50 values of 9.8–35.9 µM, superior to the positive control doxorubicin, and most showed potent anticancer activities against the HepG2 cell line.