Exploring Schiff bases derived from 4-(diethylamino)salicylaldehyde and their copper(II) complexes as antidiabetes and antioxidant agents: Structural elucidation, DFT computational and in vitro studies

IF 2.7 3区化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR

Inorganica Chimica Acta Pub Date : 2024-11-13 DOI:10.1016/j.ica.2024.122447

Segun D. Oladipo , Robert C. Luckay , Kolawole A. Olofinsan , Abosede A. Badeji , Sithabile Mokoena

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Abstract

A series of three Schiff base ligands and their metal complexes with copper(II) have been prepared. The ligands are (E)-5-(diethylamino)-2-(((2,6-dimethylphenyl)imino)methyl)phenol (C1), (E)-5-(diethylamino)-2-(((2,6-diisopropylphenyl)imino)methyl)phenol (C2) and (E)-5-(diethylamino)-2-((mesitylimino)methyl)phenol (C3). They were reacted with copper(II) nitrate trihydrate (Cu(NO₃)₂·3H₂O) to give [Cu(C1)₂] (1), [Cu(C2)₂] (2), and [Cu(C3)₂] (3). All the synthesized compounds were elucidated by exploring mass, FT-IR, UV–Vis, and NMR (¹H &¹³C) spectroscopic techniques while elemental analysis was carried out to affirm their purity. The paramagnetic nature of 1, 2 and 3 was established using EPR spectra. The molecular structure of C1 and C2 were further confirmed using single crystal X-ray crystallography. The bond lengths of C7N1, C7C8 and C8C9 obtained from structural analysis for C1 and C2 depicted their enol-tautomeric characteristic form. Quantum chemical calculations revealed that all the compounds have small energy band gaps (ΔE) with complex 2 having the lowest ΔE of 0.21 eV. The antidiabetes potential of the compounds were evaluated using α-amylase and α-glucosidase assays. Compound C1 with an IC₅₀ value of 0.11 mM, displayed almost equal α-amylase inhibition capacity as the one for acarbose (reference drug) with IC₅₀ value of 0.07 mM. Compounds C3 and 2 displayed good α-glucosidase inhibition activities with IC₅₀ value of 0.05 mM and 0.19 mM respectively. The synthesized compounds displayed moderate to excellent antioxidant potential. Complex 1 and the ligands (C1–C3) have lower IC₅₀ value than quercetin (reference drug) for nitric oxide assay. Estimated physicochemical parameters revealed that C1 and C3 fell within the threshold of Lipinski’s rule of five (Ro5) while C2 as well as complex 1–3 deviates minimally.

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探索源自 4-(二乙氨基)水杨醛的希夫碱及其铜（II）配合物作为抗糖尿病和抗氧化剂：结构阐释、DFT 计算和体外研究

我们制备了一系列三种希夫碱配体及其与铜（II）的金属配合物。这些配体分别是(E)-5-(二乙基氨基)-2-(((2,6-二甲基苯基)亚氨基)甲基)苯酚（C1）、(E)-5-(二乙基氨基)-2-(((2,6-二异丙基苯基)亚氨基)甲基)苯酚（C2）和(E)-5-(二乙基氨基)-2-((甲磺酰亚胺)甲基)苯酚（C3）。它们与三水硝酸铜（Cu(NO3)2-3H2O）反应生成[Cu(C1)2]（1）、[Cu(C2)2]（2）和[Cu(C3)2]（3）。所有合成化合物都通过质量、傅立叶变换红外光谱、紫外可见光谱和核磁共振（1H &13C ）光谱技术进行了阐释，同时还进行了元素分析以确定其纯度。利用 EPR 光谱确定了 1、2 和 3 的顺磁性。利用单晶 X 射线晶体学进一步确认了 C1 和 C2 的分子结构。从 C1 和 C2 的结构分析中得到的 C7N1、C7C8 和 C8C9 的键长描述了它们的烯醇-同分异构体特征形式。量子化学计算显示，所有化合物的能带隙（ΔE）都很小，其中复合物 2 的ΔE 最低，为 0.21 eV。利用α-淀粉酶和α-葡萄糖苷酶测定法评估了化合物的抗糖尿病潜力。化合物 C1 的 IC50 值为 0.11 mM，与 IC50 值为 0.07 mM 的阿卡波糖（参考药物）的α-淀粉酶抑制能力几乎相同。化合物 C3 和 2 显示出良好的 α-葡萄糖苷酶抑制活性，IC50 值分别为 0.05 mM 和 0.19 mM。合成的化合物显示出中等到卓越的抗氧化潜力。复合物 1 和配体（C1-C3）在一氧化氮检测中的 IC50 值低于槲皮素（参考药物）。估算的理化参数显示，C1 和 C3 在利宾斯基 5 规则（Ro5）的阈值范围内，而 C2 以及复合物 1-3 的偏差很小。

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来源期刊

Inorganica Chimica Acta 化学-无机化学与核化学

CiteScore

6.00

自引率

3.60%

发文量

440

审稿时长

35 days

期刊介绍： Inorganica Chimica Acta is an established international forum for all aspects of advanced Inorganic Chemistry. Original papers of high scientific level and interest are published in the form of Articles and Reviews. Topics covered include: • chemistry of the main group elements and the d- and f-block metals, including the synthesis, characterization and reactivity of coordination, organometallic, biomimetic, supramolecular coordination compounds, including associated computational studies; • synthesis, physico-chemical properties, applications of molecule-based nano-scaled clusters and nanomaterials designed using the principles of coordination chemistry, as well as coordination polymers (CPs), metal-organic frameworks (MOFs), metal-organic polyhedra (MPOs); • reaction mechanisms and physico-chemical investigations computational studies of metalloenzymes and their models; • applications of inorganic compounds, metallodrugs and molecule-based materials. Papers composed primarily of structural reports will typically not be considered for publication.