Nitrosation of 5H-thiazolo[3,2-a]pyrimidin-3(2H)-ones

Lashmanova, E. A.; Shiryaev, A. K.

doi:10.1007/s10593-015-1710-9

Cited by 10 publications

(2 citation statements)

References 9 publications

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“…According to the literature procedure 28 a mixture of corresponding DHPMs (1 mmol) and ethyl chloroacetate (1 ml, 90 mmol) was heated for 30 min at 110–115° C. The solution was cooled, and the precipitate was filtered off and washed with EtOAc. The prepared hydrochloride was dissolved in EtOH (10 mL) and ammonia was added to adjust pH 7.5–8.0.…”

Section: Exprimentalmentioning

confidence: 99%

“…Thiazolopyrimidines and their derivatives possess various pharmacological properties such as anticancer 22 , antibacterial 23 , anti-inflammatory 24 . Thiazolo [3,2-a] pyrimidin-3(2H)-ones, due to the active methylene carbon at C-2, have been used as starting materials for synthesizing various organic compounds such as thioindigo-like compounds 25 , 2-benzylidene 26 , 2-arylhydrazono 27 and 2-oxyimino 28 derivatives. Up to now, application of laccases in preparation of new thiazolo [3,2-a] pyrimidin-3(2H)-one’s derivatives which include a gem-dicatechol has not been reported.…”

Section: Introductionmentioning

confidence: 99%

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

Shahedi

Shahani

Habibi

et al. 2022

Sci Rep

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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.

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Section: Exprimentalmentioning

confidence: 99%