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Design and stereoselective synthesis of novel β-lactone and β-lactams as potent anticancer agents on breast cancer cells
Tetrahedron ( IF 2.1 ) Pub Date : 2018-01-11 , DOI: 10.1016/j.tet.2017.12.044
Mahnoosh Rashidi , Mohammad Reza Islami , Saeed Esmaeili-Mahani

To produce a novel class of anticancer compounds, an efficient method for synthesizing novel β-lactone and β-lactam frameworks was developed based on the reaction of a new ketene with C=O and C=N bonds. Functionalized 2-azetidinones were efficiently synthesized by employing 2,4-dichlorophenoxylketene, which was generated in situ. The reaction of the ketene with aldehydes was not successful and in all cases except for 4-nitrobenzaldehyde, a rearranged dimer of the ketene was obtained as a lactone. Anticancer cellular activity of all new β-lactams and lactones on breast cancer cells was studied. All new synthesized compounds exhibited potential anticancer activity which may guarantee their future application in moderate chemotherapy.



中文翻译:

新型β-内酯和β-内酰胺类化合物作为乳腺癌细胞有效抗癌剂的设计和立体选择性合成

为了生产一类新型的抗癌化合物,基于新的烯酮与C = O和C = N键的反应,开发了一种有效的合成新型β-内酯和β-内酰胺骨架的方法。通过使用原位生成的2,4-二氯苯氧基乙烯酮,可以有效地合成功能化的2-氮杂环丁酮。乙烯酮与醛的反应不成功,并且在所有情况下,除了4-硝基苯甲醛以外,都获得了乙烯酮的重排二聚体作为内酯。研究了所有新的β-内酰胺和内酯对乳腺癌细胞的抗癌活性。所有新合成的化合物均显示出潜在的抗癌活性,这可能保证其将来在中度化疗中的应用。

更新日期:2018-01-11
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