Design, synthesis, molecular modeling and anticholinesterase activity of benzylidene-benzofuran-3-ones containing cyclic amine side chain
AIM: A series of 2-benzylidene-benzofuran-3-ones were designed from the structures of Ebselen analogs and aurone derivatives and synthesized in good yields.
MATERIALS & METHODS: The target compounds were prepared by the condensation reaction between appropriate benzofuranones with amino alkoxy aldehydes and evaluated as cholinesterase inhibitors by Ellman's method.
RESULTS: The in vitro anti-acetylcholinesterase (AChE)/butyrylcholinesterase activities of the synthesized compounds revealed that 7e (IC50 = 0.045 μM) is the most active compound against AChE. Furthermore, the docking study confirmed the results obtained through in vitro experiments and predicted the possible binding conformation.
CONCLUSION: The anticholinesterase activities of benzylidene-benzofurane-3-ones as aurone analogs revealed that the compounds bearing piperidinylethoxy residue showed better activities against AChE, introducing these compounds for further drug discovery developments. [Formula: see text].
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2017 |
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| Erschienen: |
2017 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:9 |
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| Enthalten in: |
Future medicinal chemistry - 9(2017), 7 vom: 19. Mai, Seite 659-671 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Mehrabi, Farzad [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 11.07.2017 Date Revised 14.02.2018 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.4155/fmc-2016-0237 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM271708794 |
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| 041 | |a eng | ||
| 100 | 1 | |a Mehrabi, Farzad |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Design, synthesis, molecular modeling and anticholinesterase activity of benzylidene-benzofuran-3-ones containing cyclic amine side chain |
| 264 | 1 | |c 2017 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 11.07.2017 | ||
| 500 | |a Date Revised 14.02.2018 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a AIM: A series of 2-benzylidene-benzofuran-3-ones were designed from the structures of Ebselen analogs and aurone derivatives and synthesized in good yields | ||
| 520 | |a MATERIALS & METHODS: The target compounds were prepared by the condensation reaction between appropriate benzofuranones with amino alkoxy aldehydes and evaluated as cholinesterase inhibitors by Ellman's method | ||
| 520 | |a RESULTS: The in vitro anti-acetylcholinesterase (AChE)/butyrylcholinesterase activities of the synthesized compounds revealed that 7e (IC50 = 0.045 μM) is the most active compound against AChE. Furthermore, the docking study confirmed the results obtained through in vitro experiments and predicted the possible binding conformation | ||
| 520 | |a CONCLUSION: The anticholinesterase activities of benzylidene-benzofurane-3-ones as aurone analogs revealed that the compounds bearing piperidinylethoxy residue showed better activities against AChE, introducing these compounds for further drug discovery developments. [Formula: see text] | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a Alzheimer’s disease | |
| 650 | 4 | |a acetylcholinesterase inhibitors | |
| 650 | 4 | |a benzofuran-3-one | |
| 650 | 7 | |a 2-(4-(2-(piperidin-1-yl)ethoxy)benzylidene)-6-ethoxybenzofuran-3(2H)-one |2 NLM | |
| 650 | 7 | |a Benzofurans |2 NLM | |
| 650 | 7 | |a Benzylidene Compounds |2 NLM | |
| 650 | 7 | |a Cholinesterase Inhibitors |2 NLM | |
| 650 | 7 | |a aurone |2 NLM | |
| 650 | 7 | |a Acetylcholinesterase |2 NLM | |
| 650 | 7 | |a EC 3.1.1.7 |2 NLM | |
| 650 | 7 | |a Butyrylcholinesterase |2 NLM | |
| 650 | 7 | |a EC 3.1.1.8 |2 NLM | |
| 700 | 1 | |a Pourshojaei, Yaghoub |e verfasserin |4 aut | |
| 700 | 1 | |a Moradi, Alireza |e verfasserin |4 aut | |
| 700 | 1 | |a Sharifzadeh, Mohammad |e verfasserin |4 aut | |
| 700 | 1 | |a Khosravani, Leila |e verfasserin |4 aut | |
| 700 | 1 | |a Sabourian, Reyhaneh |e verfasserin |4 aut | |
| 700 | 1 | |a Rahmani-Nezhad, Samira |e verfasserin |4 aut | |
| 700 | 1 | |a Mohammadi-Khanaposhtani, Maryam |e verfasserin |4 aut | |
| 700 | 1 | |a Mahdavi, Mohammad |e verfasserin |4 aut | |
| 700 | 1 | |a Asadipour, Ali |e verfasserin |4 aut | |
| 700 | 1 | |a Rahimi, Hamid Reza |e verfasserin |4 aut | |
| 700 | 1 | |a Moghimi, Setareh |e verfasserin |4 aut | |
| 700 | 1 | |a Foroumadi, Alireza |e verfasserin |4 aut | |
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