Green procedures for synthesizing potential hNMDA receptor allosteric modulators through reduction and one-pot reductive acetylation of nitro(hetero)arenes using a superparamagnetic Fe(3)O(4)@APTMS@Cp(2)ZrCl (x (x = 0, 1, 2)) nanocatalyst

利用超顺磁性 Fe(3)O(4)@APTMS@Cp(2)ZrCl (x (x = 0, 1, 2)) 纳米催化剂,通过硝基(杂)芳烃的还原和一锅法还原乙酰化,绿色合成潜在的 hNMDA 受体变构调节剂

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Abstract

The conversion of nitro(hetero)arenes to corresponding (hetero)aryl amines and other practical organic compounds plays a crucial role in various sciences, especially environmental remediation and public health. In the current research work, diverse green and efficient strategies for the convenient reduction (hydrogenation) and one-pot two-step reductive acetylation of nitro(hetero)arenes using a core-shell-type mesoporous zirconocene-containing magnetically recoverable nanocomposite (viz. Fe(3)O(4)@APTMS@Cp(2)ZrCl (x (x = 0, 1, 2))) as a powerful nanocatalytic system have been developed. In the presented organic transformations, the superparamagnetic Fe(3)O(4)@APTMS@Cp(2)ZrCl (x (x = 0, 1, 2)) nanocomposite exhibited satisfactory turnover numbers (TONs) and turnover frequencies (TOFs), along with acceptable reusability. On the other hand, we investigated the potential biological effect of the synthesized (hetero)aryl amines and N-(hetero)aryl acetamides against the transmembrane domain (TMD) of the human N-methyl-d-aspartate (hNMDA) receptor based on molecular docking studies. Furthermore, the drug-likeness properties of our hit compound (viz. N-(3-(1-hydroxyethyl)phenyl)acetamide) have been scrutinized by in silico ADMET analyses.

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