Facial Regioselective Synthesis of Novel Bioactive Spiropyrrolidine/Pyrrolizine-Oxindole Derivatives via a Three Components Reaction as Potential Antimicrobial Agents

This article presents the synthesis of new derivatives of spirooxindole-spiropiperidinone- pyrrolidines 6a–j and spirooxindole-spiropiperidinone-pyrrolizines 8a–j, through a 1,3-dipolar cycloaddition reaction of azomethineylides generated from isatin, sarcosine, and l-proline, through a decarboxylat...

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Main Authors: Huwaida M. E. Hassaneen, Elshimaa M. Eid, Hamid A. Eid, Thoraya A. Farghaly, Yahia Nasser Mabkhot
Format: Article
Language:English
Published: MDPI AG 2017-02-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/22/3/357
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author Huwaida M. E. Hassaneen
Elshimaa M. Eid
Hamid A. Eid
Thoraya A. Farghaly
Yahia Nasser Mabkhot
author_facet Huwaida M. E. Hassaneen
Elshimaa M. Eid
Hamid A. Eid
Thoraya A. Farghaly
Yahia Nasser Mabkhot
author_sort Huwaida M. E. Hassaneen
collection DOAJ
description This article presents the synthesis of new derivatives of spirooxindole-spiropiperidinone- pyrrolidines 6a–j and spirooxindole-spiropiperidinone-pyrrolizines 8a–j, through a 1,3-dipolar cycloaddition reaction of azomethineylides generated from isatin, sarcosine, and l-proline, through a decarboxylative route with dipolarophile 4a–j. All of the newly synthesized compounds were evaluated for their antimicrobial activities and their minimum inhibitory concentration (MIC) against most of the test organisms. The tested compounds displayed excellent activity against all of the tested microorganisms.
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spelling doaj.art-4e68302d465e438d8b9a1c75d3f94d9d2022-12-21T23:23:54ZengMDPI AGMolecules1420-30492017-02-0122335710.3390/molecules22030357molecules22030357Facial Regioselective Synthesis of Novel Bioactive Spiropyrrolidine/Pyrrolizine-Oxindole Derivatives via a Three Components Reaction as Potential Antimicrobial AgentsHuwaida M. E. Hassaneen0Elshimaa M. Eid1Hamid A. Eid2Thoraya A. Farghaly3Yahia Nasser Mabkhot4Chemistry Department, Faculty of Science, Cairo University, Giza 12613, EgyptChemistry Department, Faculty of Science, Cairo University, Giza 12613, EgyptChemistry Department, Faculty of Science, Cairo University, Giza 12613, EgyptChemistry Department, Faculty of Science, Cairo University, Giza 12613, EgyptDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh-11451, Saudi ArabiaThis article presents the synthesis of new derivatives of spirooxindole-spiropiperidinone- pyrrolidines 6a–j and spirooxindole-spiropiperidinone-pyrrolizines 8a–j, through a 1,3-dipolar cycloaddition reaction of azomethineylides generated from isatin, sarcosine, and l-proline, through a decarboxylative route with dipolarophile 4a–j. All of the newly synthesized compounds were evaluated for their antimicrobial activities and their minimum inhibitory concentration (MIC) against most of the test organisms. The tested compounds displayed excellent activity against all of the tested microorganisms.http://www.mdpi.com/1420-3049/22/3/357isatinsarcosinel-prolineazomethineylide1,3-dipolar cycloadditionantimicrobial activity
spellingShingle Huwaida M. E. Hassaneen
Elshimaa M. Eid
Hamid A. Eid
Thoraya A. Farghaly
Yahia Nasser Mabkhot
Facial Regioselective Synthesis of Novel Bioactive Spiropyrrolidine/Pyrrolizine-Oxindole Derivatives via a Three Components Reaction as Potential Antimicrobial Agents
Molecules
isatin
sarcosine
l-proline
azomethineylide
1,3-dipolar cycloaddition
antimicrobial activity
title Facial Regioselective Synthesis of Novel Bioactive Spiropyrrolidine/Pyrrolizine-Oxindole Derivatives via a Three Components Reaction as Potential Antimicrobial Agents
title_full Facial Regioselective Synthesis of Novel Bioactive Spiropyrrolidine/Pyrrolizine-Oxindole Derivatives via a Three Components Reaction as Potential Antimicrobial Agents
title_fullStr Facial Regioselective Synthesis of Novel Bioactive Spiropyrrolidine/Pyrrolizine-Oxindole Derivatives via a Three Components Reaction as Potential Antimicrobial Agents
title_full_unstemmed Facial Regioselective Synthesis of Novel Bioactive Spiropyrrolidine/Pyrrolizine-Oxindole Derivatives via a Three Components Reaction as Potential Antimicrobial Agents
title_short Facial Regioselective Synthesis of Novel Bioactive Spiropyrrolidine/Pyrrolizine-Oxindole Derivatives via a Three Components Reaction as Potential Antimicrobial Agents
title_sort facial regioselective synthesis of novel bioactive spiropyrrolidine pyrrolizine oxindole derivatives via a three components reaction as potential antimicrobial agents
topic isatin
sarcosine
l-proline
azomethineylide
1,3-dipolar cycloaddition
antimicrobial activity
url http://www.mdpi.com/1420-3049/22/3/357
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