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- Title
Parallel synthesis of condensed pyrimidine-thiones and their antitumor activities.
- Authors
Song, Buer; Nie, Lifei; Bozorov, Khurshed; Kuryazov, Rustamkhon; Aisa, Haji Akber; Zhao, Jiangyu
- Abstract
Herein, we studied the formation of thiones via C=O group conversion into the C=S functional group-based tricyclic pyrimidinone systems using Lawesson's reagent and phosphorus pentasulfide as thionation agents. Naturally occurring alkaloids deoxyvasicinone and mackinazolinone were selected as templates for the modification 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 1H-NMR, 13C-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-(trifluoromethyl)phenyl)-1,6,7,8,9,10-hexahydro-4H-pyrrolo[2',3':4,5]pyrimido[1,2-a]azepine-4-thione) was most active derivative (IC50 = 2.09 ± 0.22 µM) against the HT-29 cell line.
- Subjects
ANTINEOPLASTIC agents; COMBINATORIAL chemistry; SMALL molecules; THIONES; SULFURATION
- Publication
Research on Chemical Intermediates, 2023, Vol 49, Issue 4, p1327
- ISSN
0922-6168
- Publication type
Article
- DOI
10.1007/s11164-022-04912-5