Antimicrobial evaluation of spirooxindolopyrrolidine engrafted indoles against multidrug resistant ESKAPE clinical pathogens

The synthesis of a new class of effective antibiotics and antimicrobial agents with less toxicity is highly desirable due to bacterial resistance to antibiotics has increased dramatically. In this context, molecules that embedding a spiro moiety are attractive from a medicinal chemistry point of vie...

Full description

Bibliographic Details
Main Authors: Natarajan Arumugam, Khloud Ibrahim Al-Shemaimari, Mohammad Altaf, Karuppiah Ponmurugan, Dhanaraj Premnath, Sinouvassane Djearamane, Ling Shing Wong, Saminathan Kayarohanam
Format: Article
Language:English
Published: Elsevier 2024-01-01
Series:Journal of King Saud University: Science
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S1018364723004585
_version_ 1827753323284922368
author Natarajan Arumugam
Khloud Ibrahim Al-Shemaimari
Mohammad Altaf
Karuppiah Ponmurugan
Dhanaraj Premnath
Sinouvassane Djearamane
Ling Shing Wong
Saminathan Kayarohanam
author_facet Natarajan Arumugam
Khloud Ibrahim Al-Shemaimari
Mohammad Altaf
Karuppiah Ponmurugan
Dhanaraj Premnath
Sinouvassane Djearamane
Ling Shing Wong
Saminathan Kayarohanam
author_sort Natarajan Arumugam
collection DOAJ
description The synthesis of a new class of effective antibiotics and antimicrobial agents with less toxicity is highly desirable due to bacterial resistance to antibiotics has increased dramatically. In this context, molecules that embedding a spiro moiety are attractive from a medicinal chemistry point of view as these spiro heterocycles show a vital part in the development of delivery systems for antimicrobial therapies. In the present study, the synthesis and antimicrobial evaluation of structurally attractive complex hybrid heterocycles comprising spriooxindolopyrrolidine and indole heterocycles was attained in quantitative yields by cycloaddition strategy. The new class of spirocompouds were unequivocally assigned through spectroscopic analysis and the antimicrobial efficacy were assessed against six microbial pathogens. Among them, compound 4a, bearing chlorine substituted derivative showed significant activity against tested ESKAPE pathogens. The maximum zone of inhibition observed against ESKAPE microbial pathogens causing infectious disease ranged from 6.75 ± 0.40 to 19.75 ± 1.15 mm, with MIC values ranging between 16.00 to  > 256.00 µg/ml .
first_indexed 2024-03-11T07:33:32Z
format Article
id doaj.art-0a3e2875a6c243b2b701f21ed9b7e89f
institution Directory Open Access Journal
issn 1018-3647
language English
last_indexed 2024-03-11T07:33:32Z
publishDate 2024-01-01
publisher Elsevier
record_format Article
series Journal of King Saud University: Science
spelling doaj.art-0a3e2875a6c243b2b701f21ed9b7e89f2023-11-17T05:25:23ZengElsevierJournal of King Saud University: Science1018-36472024-01-01361102996Antimicrobial evaluation of spirooxindolopyrrolidine engrafted indoles against multidrug resistant ESKAPE clinical pathogensNatarajan Arumugam0Khloud Ibrahim Al-Shemaimari1Mohammad Altaf2Karuppiah Ponmurugan3Dhanaraj Premnath4Sinouvassane Djearamane5Ling Shing Wong6Saminathan Kayarohanam7Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia; Corresponding authors.Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Botany and Microbiology, College of Science, P.O. Box 2455, King Saud University, Riyadh 11451, Saudi ArabiaDepartment of Biotechnology, Karunya Institute of Technology and Sciences, Coimbatore, Tamil Nadu, IndiaBiomedical Research Unit and Lab Animal Research Centre, Saveetha Dental College, Saveetha Institute of Medical and Technical Sciences, Saveetha University, Chennai 602 105, India; Faculty of Science, Universiti Tunku Abdul Rahman, Jalan Universiti, Bandar Barat, Kampar 31900, Malaysia; Corresponding authors.Faculty of Health and Life Sciences, INTI International University, Nilai 71800, MalaysiaFaculty of Bioeconomics and Health Sciences, Geomatika University Malaysia, Kuala Lumpur 54200, MalaysiaThe synthesis of a new class of effective antibiotics and antimicrobial agents with less toxicity is highly desirable due to bacterial resistance to antibiotics has increased dramatically. In this context, molecules that embedding a spiro moiety are attractive from a medicinal chemistry point of view as these spiro heterocycles show a vital part in the development of delivery systems for antimicrobial therapies. In the present study, the synthesis and antimicrobial evaluation of structurally attractive complex hybrid heterocycles comprising spriooxindolopyrrolidine and indole heterocycles was attained in quantitative yields by cycloaddition strategy. The new class of spirocompouds were unequivocally assigned through spectroscopic analysis and the antimicrobial efficacy were assessed against six microbial pathogens. Among them, compound 4a, bearing chlorine substituted derivative showed significant activity against tested ESKAPE pathogens. The maximum zone of inhibition observed against ESKAPE microbial pathogens causing infectious disease ranged from 6.75 ± 0.40 to 19.75 ± 1.15 mm, with MIC values ranging between 16.00 to  > 256.00 µg/ml .http://www.sciencedirect.com/science/article/pii/S1018364723004585Multidrug resistantESKAPE pathogensSpiropyrrolidinesCycloaddition reactionHuman health
spellingShingle Natarajan Arumugam
Khloud Ibrahim Al-Shemaimari
Mohammad Altaf
Karuppiah Ponmurugan
Dhanaraj Premnath
Sinouvassane Djearamane
Ling Shing Wong
Saminathan Kayarohanam
Antimicrobial evaluation of spirooxindolopyrrolidine engrafted indoles against multidrug resistant ESKAPE clinical pathogens
Journal of King Saud University: Science
Multidrug resistant
ESKAPE pathogens
Spiropyrrolidines
Cycloaddition reaction
Human health
title Antimicrobial evaluation of spirooxindolopyrrolidine engrafted indoles against multidrug resistant ESKAPE clinical pathogens
title_full Antimicrobial evaluation of spirooxindolopyrrolidine engrafted indoles against multidrug resistant ESKAPE clinical pathogens
title_fullStr Antimicrobial evaluation of spirooxindolopyrrolidine engrafted indoles against multidrug resistant ESKAPE clinical pathogens
title_full_unstemmed Antimicrobial evaluation of spirooxindolopyrrolidine engrafted indoles against multidrug resistant ESKAPE clinical pathogens
title_short Antimicrobial evaluation of spirooxindolopyrrolidine engrafted indoles against multidrug resistant ESKAPE clinical pathogens
title_sort antimicrobial evaluation of spirooxindolopyrrolidine engrafted indoles against multidrug resistant eskape clinical pathogens
topic Multidrug resistant
ESKAPE pathogens
Spiropyrrolidines
Cycloaddition reaction
Human health
url http://www.sciencedirect.com/science/article/pii/S1018364723004585
work_keys_str_mv AT natarajanarumugam antimicrobialevaluationofspirooxindolopyrrolidineengraftedindolesagainstmultidrugresistanteskapeclinicalpathogens
AT khloudibrahimalshemaimari antimicrobialevaluationofspirooxindolopyrrolidineengraftedindolesagainstmultidrugresistanteskapeclinicalpathogens
AT mohammadaltaf antimicrobialevaluationofspirooxindolopyrrolidineengraftedindolesagainstmultidrugresistanteskapeclinicalpathogens
AT karuppiahponmurugan antimicrobialevaluationofspirooxindolopyrrolidineengraftedindolesagainstmultidrugresistanteskapeclinicalpathogens
AT dhanarajpremnath antimicrobialevaluationofspirooxindolopyrrolidineengraftedindolesagainstmultidrugresistanteskapeclinicalpathogens
AT sinouvassanedjearamane antimicrobialevaluationofspirooxindolopyrrolidineengraftedindolesagainstmultidrugresistanteskapeclinicalpathogens
AT lingshingwong antimicrobialevaluationofspirooxindolopyrrolidineengraftedindolesagainstmultidrugresistanteskapeclinicalpathogens
AT saminathankayarohanam antimicrobialevaluationofspirooxindolopyrrolidineengraftedindolesagainstmultidrugresistanteskapeclinicalpathogens