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

Chemistry and Physics

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

A set of dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]8a-lwas regioselectively synthesized utilizing multi-component azomethine cycloaddition reaction of 3-(arylmethylidene)pyrrolidine-2,5-diones5a-e, isatins6a-cand sarcosine7. Single crystal X-ray studies of8cadd conclusive support for the structure. Compounds8eand8greveal 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.

Original language	English (US)
Pages (from-to)	21830-21838
Number of pages	9
Journal	RSC Advances
Volume	10
Issue number	37
DOIs	https://doi.org/10.1039/d0ra03064c
State	Published - Jun 8 2020

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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@article{4c860935f60641c58194c22b6c721c84,

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

abstract = "A set of dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]8a-lwas regioselectively synthesized utilizing multi-component azomethine cycloaddition reaction of 3-(arylmethylidene)pyrrolidine-2,5-diones5a-e, isatins6a-cand sarcosine7. Single crystal X-ray studies of8cadd conclusive support for the structure. Compounds8eand8greveal 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.",

author = "Youssef, {M. Adel} and Panda, {Siva S.} and El-Shiekh, {Riham A.} and Shalaby, {El Sayed M.} and Aboshouk, {Dalia R.} and Walid Fayad and Fawzy, {Nehmedo G.} and Girgis, {Adel S.}",

note = "Funding Information: This work was supported financially by National Research Centre, Egypt, project ID: 12060101. Funding Information: This work was supported nancially by National Research Centre, Egypt, project ID: 12060101. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2020.",

year = "2020",

month = jun,

day = "8",

doi = "10.1039/d0ra03064c",

language = "English (US)",

volume = "10",

pages = "21830--21838",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "37",

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T1 - Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]

AU - Youssef, M. Adel

AU - Panda, Siva S.

AU - El-Shiekh, Riham A.

AU - Shalaby, El Sayed M.

AU - Aboshouk, Dalia R.

AU - Fayad, Walid

AU - Fawzy, Nehmedo G.

AU - Girgis, Adel S.

N1 - Funding Information: This work was supported financially by National Research Centre, Egypt, project ID: 12060101. Funding Information: This work was supported nancially by National Research Centre, Egypt, project ID: 12060101. Publisher Copyright: © The Royal Society of Chemistry 2020.

PY - 2020/6/8

Y1 - 2020/6/8

N2 - A set of dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]8a-lwas regioselectively synthesized utilizing multi-component azomethine cycloaddition reaction of 3-(arylmethylidene)pyrrolidine-2,5-diones5a-e, isatins6a-cand sarcosine7. Single crystal X-ray studies of8cadd conclusive support for the structure. Compounds8eand8greveal 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.

AB - A set of dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]8a-lwas regioselectively synthesized utilizing multi-component azomethine cycloaddition reaction of 3-(arylmethylidene)pyrrolidine-2,5-diones5a-e, isatins6a-cand sarcosine7. Single crystal X-ray studies of8cadd conclusive support for the structure. Compounds8eand8greveal 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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Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]

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