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Reductive domino reaction to access chromeno[2,3-c]isoquinoline-5-amines with antiproliferative activities against human tumor cells.
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2020-08-28 , DOI: 10.1016/j.bioorg.2020.104169
Xiaoyi Yue 1 , Alexey A Festa 1 , Olga A Storozhenko 1 , Alexey V Varlamov 1 , Karthikeyan Subramani 1 , Angelina Boccarelli 2 , Rosa Purgatorio 3 , Cosimo D Altomare 3 , Leonid G Voskressensky 1
Affiliation  

An interaction of homophthalonitrile with salicylaldehydes proceeds as a novel domino reaction and results in the formation of nineteen 12H-chromeno[2,3-c]isoquinoline-5-amine derivatives. Four new bonds and two cycles are forged in a single synthetic operation, employing cheap and eco-friendly ammonium formate, acting both as a catalyst and a reducing agent. The in vitro cytotoxicity tests revealed antiproliferative activities against five human tumor cell lines, including the cisplatin-resistant ovarian carcinoma one (A2780cp8), with inhibitory potency data (IC50) in the low micromolar range in most cases. Molecular docking calculations and fluorescence quenching studies revealed possible binding properties with DNA of the active compounds.



中文翻译:

还原多米诺反应,获得具有抗人类肿瘤细胞增殖活性的chromeno [2,3-c] isoquinoline-5-amines。

高纯邻苯二甲腈与水杨醛的相互作用作为一种新型的多米诺骨牌反应而进行,并导致形成19个12 H -chromeno [2,3 - c ] isoquinoline-5-amine衍生物。一次合成操作即可锻造四个新的键和两个循环,使用廉价且环保的甲酸铵,既充当催化剂又充当还原剂。体外细胞毒性测试显示了对五种人类肿瘤细胞系的抗增殖活性,包括一种对顺铂耐药的卵巢癌(A2780cp8),在大多数情况下,其抑制力数据(IC 50)在低微摩尔范围内。分子对接计算和荧光猝灭研究表明,活性化合物可能与DNA结合。

更新日期:2020-09-10
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