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Cholinesterase inhibitory activity and regioselective synthesis of spiropyrrolidinoindole integrated ferrocene hybrid heterocycles via multicomponent cycloaddition reaction
Journal of King Saud University-Science ( IF 3.8 ) Pub Date : 2023-11-24 , DOI: 10.1016/j.jksus.2023.103027
Abdulrahman I. Almansour , Khloud Ibrahim Al-Shemaimari , Shatha Ibhrahim Alaqeel

A novel spiroheterocyclic hybrid comprising several privileged structures comprising pyrrolidine, quinoxaline, indole and ferrocene moieties were synthesized in good yields in sustainable fashion using [Bmim]Br augmented four component cycloaddition process. A relatively less explored ylide prepared from quinoxalinone and L-tryptophan with diverse ferrocenyl derivatives in ionic liquids afforded spiropyrrolidinoindole tethered ferrocene hybrids. The reaction provides highly regioselective fashion thus created five new bonds and four adjoining stereocenter in single synthetic transformation, thus created with complete diastereomeric control. The cholinesterase inhibitory potency was performed for synthesized compounds against AChE/BChE enzymes. Among them, compound bearing with fluorine substituted heterocycles showed significant activity which is comparable activity with reference standard, galantamine.



中文翻译:

胆碱酯酶抑制活性及通过多组分环加成反应区域选择性合成螺吡咯烷吲哚集成二茂铁杂环

使用[Bmim]Br增强四组分环加成工艺,以可持续的方式以良好的产率合成了一种新型螺杂环杂化物,该杂化物包含几种特殊结构,其中包括吡咯烷、喹喔啉、吲哚和二茂铁部分。由喹喔啉酮和 L-色氨酸与多种二茂铁基衍生物在离子液体中制备的叶立德相对较少,得到了螺吡咯烷吲哚束缚的二茂铁杂化物。该反应提供了高度区域选择性的方式,从而在单一合成转化中产生了五个新键和四个相邻的立体中心,从而产生了完全的非对映体控制。测试了合成化合物对 AChE/BChE 酶的胆碱酯酶抑制效力。其中,带有氟取代杂环的化合物显示出显着的活性,其活性与参考标准加兰他敏相当。

更新日期:2023-11-24
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