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

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 ca...

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Published inScientific reports Vol. 12; no. 1; p. 22326
Main Authors Shahedi, Mansour, Shahani, Rojina, Habibi, Zohreh, Yousefi, Maryam, Brask, Jesper, Minaei-Tehrani, Arash, Samadi, Fatemeh Yazdi, Mohammadi, Mehdi
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 25.12.2022
Nature Publishing Group
Nature Portfolio
Subjects
639/638/224
639/638/403
Adenocarcinoma
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antitumor agents
Cancer
Carbon
Cell Proliferation - drug effects
Doxorubicin
Drug Screening Assays, Antitumor
Enzymes
Hep G2 Cells
Hepatocytes
HT29 Cells
Humanities and Social Sciences
Humans
Intermediates
Laccase - chemistry
Mass spectroscopy
Molecular Structure
multidisciplinary
NMR
Nuclear magnetic resonance
Oxidation
Pyrimidines - chemistry
Pyrimidines - pharmacology
Science
Science (multidisciplinary)
Structure-Activity Relationship
Thiazoles - chemistry
Thiazoles - pharmacology
Tumor cell lines
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Summary: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 1 H NMR, 13 C 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 IC 50 values of 9.8–35.9 µM, superior to the positive control doxorubicin, and most showed potent anticancer activities against the HepG2 cell line.
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ISSN:2045-2322
2045-2322
DOI:10.1038/s41598-022-26820-9