A facile one-pot three component synthesis of 3, 4-dihydropyrimidin-2(1H)-ones or thiones promoted by a polymer-supported BF3 under solvent-free conditions

Herein we studied the formation of thiones via C=O group conversion into the C=S functional groupbased tricyclic pyrimidinone systems using Lawesson's reagent and phosphorus pentasul de as thionation agents. Naturally-occurring alkaloids deoxyvasicinone and mackinazolinone were selected as templates for the modi cation of furo [2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone scaffold.Research work was performed under the combinatorial and parallel synthesis of pyrimidine-based small molecules, along with a one-pot reaction strategy. All synthesized 54 novel pyrimidine-thiones were elucidated by 1 H-NMR, 13 C-NMR, and HRMS analysis. In addition, both series of thiones were evaluated for their antitumor activity against three types of the human cancer cell: cervical HeLa, breast MCF-7, and colon HT-29 lines. Compound with azepine fragment 13aa (1-methyl-2-(4- 6,7,8,9,10-hexahydro-4H-pyrrolo[2',3':4,5]pyrimido[1,2-a]azepine-4-thione) was most active derivative (IC 50 =2.09±0.22 µM) against the HT-29 cell line.

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Parallel synthesis of condensed pyrimidine-thiones and their antitumor activities

Song

Nie

Bozorov

et al. 2022

Res Chem Intermed

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A facile one-pot three component synthesis of 3, 4-dihydropyrimidin-2(1H)-ones or thiones promoted by a polymer-supported BF3 under solvent-free conditions

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Parallel synthesis of condensed pyrimidine-thiones and their antitumor activities

Parallel synthesis of condensed pyrimidine-thiones and their antitumor activities

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