Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]

M. Adel Youssef; Siva S. Panda; Riham A. El-Shiekh; ElSayed M. Shalaby; Dalia R. Aboshouk; Walid Fayad; Nehmedo G. Fawzy; Adel S. Girgis

doi:10.1039/D0RA03064C

Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]†

M. Adel Youssef,^a Siva S. Panda,

^b Riham A. El-Shiekh,^c ElSayed M. Shalaby,^d Dalia R. Aboshouk,

^e Walid Fayad,^f Nehmedo G. Fawzy^e and Adel S. Girgis

*^e

Author affiliations

* Corresponding authors

^a Department of Chemistry, Faculty of Science, Helwan University, Helwan, Egypt

^b Department of Chemistry and Physics, Augusta University, Augusta, GA 30912, USA

^c Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo 11562, Egypt

^d X-Ray Crystallography Lab., Physics Division, National Research Centre, Dokki, Giza 12622, Egypt

^e Department of Pesticide Chemistry, National Research Centre, Dokki, Giza 12622, Egypt
E-mail: girgisas10@yahoo.com

^f Drug Bioassay-Cell Culture Laboratory, Pharmacognosy Department, National Research Centre, Dokki, Giza, Egypt

Abstract

A set of dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines] 8a–l was regioselectively synthesized utilizing multi-component azomethine cycloaddition reaction of 3-(arylmethylidene)pyrrolidine-2,5-diones 5a–e, isatins 6a–c and sarcosine 7. Single crystal X-ray studies of 8c add conclusive support for the structure. Compounds 8e and 8g reveal cholinesterase inhibitory properties with promising efficacy against both AChE and BChE and were found to be more selective towards AChE than BChE as indicted by the selectivity index like Donepezil (a clinically used cholinesterase inhibitory drug). Molecular modeling studies assist in understanding the bio-observations and identifying the responsible parameters behind biological properties.

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DOI: https://doi.org/10.1039/D0RA03064C
Article type: Paper
Submitted: 05 Apr 2020
Accepted: 29 May 2020
First published: 08 Jun 2020
This article is Open Access

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RSC Adv., 2020,10, 21830-21838

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Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]

M. A. Youssef, S. S. Panda, R. A. El-Shiekh, E. M. Shalaby, D. R. Aboshouk, W. Fayad, N. G. Fawzy and A. S. Girgis, RSC Adv., 2020, 10, 21830 DOI: 10.1039/D0RA03064C

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Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]†

Abstract

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Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]

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