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Ultrasounds-mediated 10-seconds synthesis of chalcones as potential farnesyltransferase inhibitors.
Bioorganic & Medicinal Chemistry Letters ( IF 2.7 ) Pub Date : 2020-03-29 , DOI: 10.1016/j.bmcl.2020.127149
Germain Homerin 1 , Adrian Sorin Nica 2 , Amaury Farce 3 , Joëlle Dubois 4 , Alina Ghinet 5
Affiliation  

A broad range of chalcones and derivatives were easily and rapidly synthesized, following Claisen-Schmidt condensation of (hetero)aryl ketones and (hetero)aryl aldehydes using a ultrasound probe. A comparison was made with classical magnetic stirring experiments, and an optimization study was realized, showing lithium hydroxide to be the best basic catalyst of the studied condensations. By-products of the reactions (β-hydroxy-ketone, diketones, and cyclohexanols) were also isolated. All compounds were evaluated in vitro for their ability to inhibit human farnesyltransferase, a protein implicated in cancer and rare diseases and on the NCI-60 cancer cell lines panel. Molecules showed inhibitory activity on the target protein and cytostatic effect on different cell lines with particular activity against MCF7, breast cancer cells.

中文翻译:

超声介导的10秒钟合成查耳酮作为潜在的法呢基转移酶抑制剂。

在使用超声探针将(杂)芳基酮和(杂)芳基醛进行克莱森-施密特缩合反应之后,可以轻松快速地合成各种查耳酮和衍生物。与经典的磁力搅拌实验进行了比较,并进行了优化研究,表明氢氧化锂是所研究缩合物的最佳碱性催化剂。还分离了反应的副产物(β-羟基酮,二酮和环己醇)。在体外评估所有化合物抑制人法呢基转移酶的能力,后者是一种与癌症和罕见疾病有关的蛋白质,在NCI-60癌细胞系中也有。分子对靶蛋白具有抑制活性,对不同细胞系具有抑制细胞的作用,对MCF7乳腺癌细胞具有特定的活性。
更新日期:2020-04-20
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