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Crystal structure, DFT calculations and evaluation of 2-(2-(3,4-dimethoxyphenyl)ethyl)isoindoline-1,3-dione as AChE inhibitor

Overview of attention for article published in BMC Chemistry, June 2018
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Title
Crystal structure, DFT calculations and evaluation of 2-(2-(3,4-dimethoxyphenyl)ethyl)isoindoline-1,3-dione as AChE inhibitor
Published in
BMC Chemistry, June 2018
DOI 10.1186/s13065-018-0442-1
Pubmed ID
Authors

Erik Andrade-Jorge, José Bribiesca-Carlos, Francisco J. Martínez-Martínez, Marvin A. Soriano-Ursúa, Itzia I. Padilla-Martínez, José G. Trujillo-Ferrara

Abstract

Dioxoisoindolines have been included as a pharmacophore group in diverse drug-like molecules with a wide range of biological activity. Various reports have shown that phthalimide derivatives are potent inhibitors of AChE, a key enzyme involved in the deterioration of the cholinergic system during the development of Alzheimer's disease. In the present study, 2-(2-(3,4-dimethoxyphenyl)ethyl)isoindoline-1,3-dione was synthesized, crystallized and evaluated as an AChE inhibitor. The geometric structure of the crystal and the theoretical compound (from molecular modeling) were analyzed and compared, finding a close correlation. The formation of the C6-H6···O19 interaction could be responsible for the non-negligible out of phenyl plane deviation of the C19 methoxy group, the O3 from the carbonyl group lead to C16-H16···O3i intermolecular interactions to furnish C(9) and C(14) infinite chains within the (- 4 0 9) and (- 3 1 1) families of planes. Finally, the biological experiments reveal that the isoindoline-1,3-dione exerts a good competitive inhibition on AChE (Ki = 0.33-0.93 mM; 95% confidence interval) and has very low acute toxicity (LD50 > 1600 mg/kg) compared to the AChE inhibitors currently approved for clinical use.

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The data shown below were compiled from readership statistics for 17 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Unknown 17 100%

Demographic breakdown

Readers by professional status Count As %
Other 3 18%
Student > Master 3 18%
Lecturer > Senior Lecturer 2 12%
Student > Bachelor 2 12%
Student > Ph. D. Student 1 6%
Other 3 18%
Unknown 3 18%
Readers by discipline Count As %
Pharmacology, Toxicology and Pharmaceutical Science 3 18%
Chemistry 3 18%
Medicine and Dentistry 2 12%
Psychology 1 6%
Unspecified 1 6%
Other 1 6%
Unknown 6 35%