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Ugi–Smiles and Ullmann reactions catalyzed by Schiff base derived from Tröger’s base and BINOL
Research on Chemical Intermediates ( IF 2.8 ) Pub Date : 2020-02-12 , DOI: 10.1007/s11164-020-04091-1
Rui Yuan , Ming-qi Li , Xuan-xuan Ren , Wen Chen , Hang Zhou , Yu Wan , Peng Zhang , Hui Wu

A Schiff base catalyst (1a) combining a Tröger’s base-NH2 and the (R)-BINOL-(CHO)2 was used to promote the Ugi-Smiles reaction. By using isocyanide, malononitrile, aldehydes and low-reactive unfunctionalized 1H-benzo[d]imidazole-2-thiols as substrates, thioimidazolidinone derivatives (6) were obtained with high yields under mild condition. Subsequently, the catalyst was used as the efficient ligand to promote the CuI-catalyzed Ullmann reaction of the products of Ugi-Smiles reaction to give imidazole-containing five-membered fused ring compounds (7). The results indicated that it is an efficient way to develop catalysts to combine TB and BINOL framework. Finally, the antitumor activities of products on human three positive breast cancer cells (MCF-7), human three negative breast cancer cells (MDA-MB-231), human alveolar epithelial cell (A549) and of cytotoxicity on human bronchial epithelial cell (HBE) of all products in vitro were evaluated. Some products showed great inhibition effect on cancer cells (IC50 on MCF-7 and MDA-MB-231 reached nanogram levels) and low toxicity to normal cells, which display their potential in the new drug development.



中文翻译:

由Tröger碱和BINOL衍生的Schiff碱催化的Ugi–Smiles和Ullmann反应

结合了Tröger碱-NH 2和(R)-BINOL-(CHO)2的席夫碱催化剂(1a)用于促进Ugi-Smiles反应。以异氰化物,丙二腈,醛和低反应性未官能化的1 H-苯并[ d ]咪唑-2-硫醇为底物,在温和条件下高收率获得了硫代咪唑啉酮衍生物(6)。随后,该催化剂用作有效的配体,以促进Ugi-Smiles反应产物的CuI催化的Ullmann反应,得到含咪唑的五元稠环化合物(7)。结果表明,这是开发结合TB和BINOL骨架的催化剂的有效方法。最后,产品对人三阳性乳腺癌细胞(MCF-7),人三阴性乳腺癌细胞(MDA-MB-231),人肺泡上皮细胞(A549)的抗肿瘤活性以及对人支气管上皮细胞的细胞毒性(评估了所有体外产品的HBE)。一些产品对癌细胞具有极大的抑制作用(MCF-7和MDA-MB-231的IC 50达到纳克水平),并且对正常细胞的毒性低,这显示了它们在新药开发中的潜力。

更新日期:2020-02-12
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