Novel cinnamic acid–tryptamine hybrids as potent butyrylcholinesterase inhibitors: Synthesis, biological evaluation, and docking study

Ghafary Shahrzad; Najafi Zahra; Mohammadi‐Khanaposhtani Maryam; Nadri Hamid; Edraki Najmeh; Ayashi Neda; Larijani Bagher; Amini Mohsen; Mahdavi Mohammad

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Novel cinnamic acid–tryptamine hybrids as potent butyrylcholinesterase inhibitors: Synthesis, biological evaluation, and docking study

机译：新型肉桂酸 - 色氨酸杂交杂交剂作为有效的丁酰胆碱酯酶抑制剂：合成，生物学评估和对接研究

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Abstract A novel series of cinnamic acid–tryptamine hybrids was designed, synthesized, and evaluated as cholinesterase inhibitors. Anticholinesterase assays showed that all of the synthesized compounds displayed a clearly selective inhibition of butyrylcholinesterase (BChE), but only a moderate inhibitory effect toward acetylcholinesterase (AChE) was detected. Among these cinnamic acid–tryptamine hybrids, compound 7d was found to be the most potent inhibitor of BChE with an IC 50 value of 0.55?±?0.04?μM. This compound showed a 14‐fold higher inhibitory potency than the standard drug donepezil (IC 50 ?=?7.79?±?0.81?μM) and inhibited BChE through a mixed‐type inhibition mode. Moreover, a docking study revealed that compound 7d binds to both the catalytic anionic site (CAS) and the peripheral anionic site (PAS) of BChE. Also, compound 7d was evaluated against β‐secretase, which exhibited low activity (inhibition percentage: 38%).

机译：摘要设计，合成，作为胆碱酯酶抑制剂设计了一种新型的肉桂酸 - 色氨酸杂交混合物。抗胆碱酯酶测定表明，所有合成的化合物都显示出明确选择性抑制丁酰胆碱酯酶（BCHE），但仅检测到对乙酰胆碱酯酶（ACHE）的中等抑制作用。在这些肉桂酸 - 色氨酸杂交中，发现化合物7d是BCHE中最有效的抑制剂，IC 50值为0.55≤0.04Ω·μm。该化合物显示出比标准药物多哌妥哌齐（IC 50 =α=α±0.81Ω×7.79±7.79）并通过混合型抑制模式抑制BCHE的14倍。此外，对接研究表明，化合物7D与BCHE的催化阴离子位点（CAS）和外周阴离子位点（PAS）结合。此外，对β-分泌酶评价化合物7D，其表现出低活性（抑制百分比：38％）。

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来源
《Archiv der Pharmazie》 |2018年第10期|共10页
作者
Ghafary Shahrzad; Najafi Zahra; Mohammadi‐Khanaposhtani Maryam; Nadri Hamid; Edraki Najmeh; Ayashi Neda; Larijani Bagher; Amini Mohsen; Mahdavi Mohammad;
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作者单位

Faculty of Pharmacy Department of Medicinal ChemistryTehran University of Medical SciencesTehran;

Department of Medicinal Chemistry School of PharmacyHamadan University of Medical SciencesHamadan;

Cellular and Molecular Biology Research Center Health Research InstituteBabol University of;

Faculty of Pharmacy Department of Medicinal ChemistryShahid Sadoughi University of Medical;

Medicinal and Natural Products Chemistry Research CenterShiraz University of Medical SciencesShiraz;

Endocrinology and Metabolism Research Center Endocrinology and Metabolism Clinical Sciences;

Endocrinology and Metabolism Research Center Endocrinology and Metabolism Clinical Sciences;

Faculty of Pharmacy Department of Medicinal ChemistryTehran University of Medical SciencesTehran;

Endocrinology and Metabolism Research Center Endocrinology and Metabolism Clinical Sciences;

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中图分类药学;
关键词
Alzheimer's disease; butyrylcholinesterase inhibitors; cholinesterase inhibition; cinnamic acid; docking study; tryptamine;

机译：阿尔茨海默病;丁酰基胆管酶抑制剂;胆碱酯酶抑制;肉桂酸;对接研究;TryPtamine;

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1. Novel cinnamic acid–tryptamine hybrids as potent butyrylcholinesterase inhibitors: Synthesis, biological evaluation, and docking study [J] . Ghafary Shahrzad, Najafi Zahra, Mohammadi‐Khanaposhtani Maryam, Archiv der Pharmazie . 2018,第10期

机译：新型肉桂酸 - 色氨酸杂交杂交剂作为有效的丁酰胆碱酯酶抑制剂：合成，生物学评估和对接研究
2. Synthesis, docking study, and biological evaluation of novel umbellipherone/hymecromone derivatives as acetylcholinesterase/butyrylcholinesterase inhibitors [J] . Moradi Alireza, Faraji Laleh, Nadri Hamid, Medicinal chemistry research: an international journal for rapid communications on design and mechanisms of action of biologically active agents . 2018,第7期

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机译：将甘蔗 - 肉桂酸杂交种的设计，合成，体内和体内评价为含有阿尔茨海默病的多靶乙酰 - 和丁二醇酯酶抑制剂

Novel cinnamic acid–tryptamine hybrids as potent butyrylcholinesterase inhibitors: Synthesis, biological evaluation, and docking study

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