Design, Green Synthesis, and Biological Evaluation of New Substituted Tetrahydropyrimidine Derivatives as Acetylcholinesterase Inhibitors
A series of novel tetrahydropyrimidin-4-yl)pyridine derivatives 6(a-h) have been designed and synthesized as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The chemical structures of all newly synthesized compounds were characterized by spectroscopic methods (IR, 1 H NMR...
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| Published in: | Polycyclic aromatic compounds Vol. 42; no. 8; pp. 5231 - 5241 |
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| Main Authors: | , , , , , |
| Format: | Journal Article |
| Language: | English |
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14-09-2022
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| Abstract | A series of novel tetrahydropyrimidin-4-yl)pyridine derivatives 6(a-h) have been designed and synthesized as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The chemical structures of all newly synthesized compounds were characterized by spectroscopic methods (IR,
1
H NMR,
13
C NMR) and elemental analyzes. The in vitro studies showed that all the synthesized derivatives showed significant BChE inhibitory activity more potent than donepezil as the standard (IC
50
values less than 0.1 µM). All the target compounds demonstrated good AChE inhibitory effects comparable with donepezil as the reference drug with IC
50
values ranging from 0.08 to 0.1 µM. The best results were obtained by 4-methyl substituted derivative 6d with IC
50
value of 0.082 µM which was comparable with AChE inhibitory effects of donepezil (IC
50
= 0.079 µM). |
|---|---|
| AbstractList | A series of novel tetrahydropyrimidin-4-yl)pyridine derivatives 6(a-h) have been designed and synthesized as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The chemical structures of all newly synthesized compounds were characterized by spectroscopic methods (IR,
1
H NMR,
13
C NMR) and elemental analyzes. The in vitro studies showed that all the synthesized derivatives showed significant BChE inhibitory activity more potent than donepezil as the standard (IC
50
values less than 0.1 µM). All the target compounds demonstrated good AChE inhibitory effects comparable with donepezil as the reference drug with IC
50
values ranging from 0.08 to 0.1 µM. The best results were obtained by 4-methyl substituted derivative 6d with IC
50
value of 0.082 µM which was comparable with AChE inhibitory effects of donepezil (IC
50
= 0.079 µM). A series of novel tetrahydropyrimidin-4-yl)pyridine derivatives 6(a–h) have been designed and synthesized as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The chemical structures of all newly synthesized compounds were characterized by spectroscopic methods (IR, 1H NMR, 13C NMR) and elemental analyzes. The in vitro studies showed that all the synthesized derivatives showed significant BChE inhibitory activity more potent than donepezil as the standard (IC50 values less than 0.1 µM). All the target compounds demonstrated good AChE inhibitory effects comparable with donepezil as the reference drug with IC50 values ranging from 0.08 to 0.1 µM. The best results were obtained by 4-methyl substituted derivative 6d with IC50 value of 0.082 µM which was comparable with AChE inhibitory effects of donepezil (IC50 = 0.079 µM). |
| Author | Zahedifar, Mahboobeh Mariki, Ali akbar Pouramiri, Behjat Anaeigoudari, Akbar Lotfi, Safa Ayati, Adileh |
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| Cites_doi | 10.1016/j.molstruc.2018.08.063 10.1021/jm950704x 10.1021/ci200227u 10.1002/cpbi.3 10.2298/JSC191231039P 10.1021/jm9803626 10.1016/0006-2952(61)90145-9 10.1351/pac200173030555 10.1002/1521-4184(200103)334:3<79::AID-ARDP79>3.0.CO;2-7 10.1055/s-0030-1258290 10.2174/092986609789071207 10.1016/j.tetlet.2011.12.134 10.1021/jm010417v 10.1021/cc700089a 10.1124/jpet.105.090365 10.1021/jm501195e 10.1002/(SICI)1098-2299(199702)40:2<171::AID-DDR7>3.0.CO;2-I 10.1002/ardp.201800167 10.1016/j.bmc.2007.03.028 10.1016/j.biopha.2018.06.147 10.1002/ardp.201300228 10.1016/j.bmcl.2012.02.056 10.1021/ml400304w 10.1016/0010-4655(95)00042-E 10.2174/138161206775193127 10.3390/molecules24122306 10.3109/14756366.2014.1003212 10.1016/j.ejmech.2011.02.073 10.1126/science.7046051 10.1002/jcc.21334 10.1021/bi300955k 10.1073/pnas.90.19.9031 10.1016/j.bioorg.2020.104457 10.1016/j.ejmech.2013.09.050 10.1016/j.ejmech.2010.10.009 |
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| Snippet | A series of novel tetrahydropyrimidin-4-yl)pyridine derivatives 6(a-h) have been designed and synthesized as inhibitors of acetylcholinesterase (AChE) and... A series of novel tetrahydropyrimidin-4-yl)pyridine derivatives 6(a–h) have been designed and synthesized as inhibitors of acetylcholinesterase (AChE) and... |
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| SubjectTerms | Acetylcholinesterase Alzheimer's disease butyrylcholinesterase inhibitors Chemical synthesis Donepezil Inhibitors NMR Nuclear magnetic resonance Substitutes tetrahydropyrimidin-4-yl)pyridine |
| Title | Design, Green Synthesis, and Biological Evaluation of New Substituted Tetrahydropyrimidine Derivatives as Acetylcholinesterase Inhibitors |
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