Synthesis and biological evaluation of substituted benzohydrazide Schiff base adduct as potential cholinesterase inhibitors

IF 2.218 Q2 Chemistry Chemical Data Collections Pub Date : 2024-06-10 DOI:10.1016/j.cdc.2024.101151

Ahmad Zulfiqar , Irshad Ullah Khan , Muhammad Nabi , Hayat Ullah , Naveed Iqbal , Benish Zeb , Amjad Hussain , Daud Khan , Abdur Rab , Sayyed Muhammad Junaid , Muhammad Taha , Syed Adnan Ali Shah , Fazal Rahim

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Abstract

A total of Twenty two (22) derivatives of benzohydrazide bearing Schiff base have been synthesized, characterized through ¹HNMR, ¹³C NMR and screened against cholinesterase inhibitory potentials. All the adducts (1–22) showed varying degree of cholinesterase inhibitory potential IC₅₀ ranging between 13.23 ± 0.02 to 59.09 ± 1.22 µM against acetylcholinesterase, with IC₅₀ values ranging from 23.55 ± 0.32 to 61.55 ± 0.58 µM against butyrylcholinesterase. Among the series analogs 1, 3, 8, 12, 14, 15, 17, 18 and 22 with IC₅₀ values 20.05 ± 0.13, 17.32 ± 0.15, 14.32 ± 0.97, 23.33 ± 0.56, 18.02 ± 0.09, 19.05 ± 0.13, 15.11 ± 0.23, 13.23 ± 0.02, and 22.57 ± 0.09 µM respectively showed excellent inhibitory potential against acetylcholinesterase and with IC₅₀ values 31.46 ± 0.98, 26.06 ± 0.08, 25.33 ± 1.49, 30.12 ± 0.78, 28.11 ± 0.5, 29.33 ± 0.19, 25.37 ± 0.47, 23.55 ± 0.32 and 33.12 ± 0.78 against butylcholinesterase as compared to the standard Galanthamine. All other analogs showed moderate inhibitory potential. A structure-activity relationship has been established for all compounds. Through molecular docking studies, the interactions between compounds with the enzyme active sites were confirmed.

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作为潜在胆碱酯酶抑制剂的取代苯甲酰肼席夫碱加合物的合成与生物学评价

通过 1HNMR、13C NMR 和胆碱酯酶抑制潜能筛选，共合成了 22 种含希夫碱的苯甲酰肼衍生物。所有加合物（1-22）都显示出不同程度的胆碱酯酶抑制潜能，对乙酰胆碱酯酶的 IC50 值在 13.23 ± 0.02 至 59.09 ± 1.22 µM 之间，对丁酰胆碱酯酶的 IC50 值在 23.55 ± 0.32 至 61.55 ± 0.58 µM 之间。系列类似物 1、3、8、12、14、15、17、18 和 22 的 IC50 值分别为 20.05 ± 0.13、17.32 ± 0.15、14.32 ± 0.97、23.33 ± 0.56、18.02 ± 0.09、19.05 ± 0.13、15.11 ± 0.23、13.23 ± 0.02 和 22.57 ± 0.09 µM。与标准品加兰他敏相比，其他类似物对乙酰胆碱酯酶的 IC50 值分别为 31.46 ± 0.98、26.06 ± 0.08、25.33 ± 1.49、30.12 ± 0.78、28.11 ± 0.5、29.33 ± 0.19、25.37 ± 0.47、23.55 ± 0.32 和 33.12 ± 0.78。所有其他类似物都显示出中等抑制潜力。所有化合物都建立了结构-活性关系。通过分子对接研究，确认了化合物与酶活性位点之间的相互作用。

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来源期刊

Chemical Data Collections Chemistry-Chemistry (all)

CiteScore

6.10

自引率

0.00%

发文量

169

审稿时长

24 days

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