Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing <i>Escherichia coli</i> and MRSA, Docking Studies, and Structural Features Determination through Computational Approach
The synthesis of new 6-Bromoquinolin-4-ol derivatives (<b>3a</b>–<b>3h</b>) by Chan–Lam coupling utilizing different types of solvents (protic, aprotic, and mixed solvents) and bases was studied in the present manuscript. Furthermore, their potential against ESBL producing &l...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-06-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/12/3732 |
| _version_ | 1827658149635555328 |
|---|---|
| author | Mahwish Arshad Nasir Rasool Muhammad Usman Qamar Syed Adnan Ali Shah Zainul Amiruddin Zakaria |
| author_facet | Mahwish Arshad Nasir Rasool Muhammad Usman Qamar Syed Adnan Ali Shah Zainul Amiruddin Zakaria |
| author_sort | Mahwish Arshad |
| collection | DOAJ |
| description | The synthesis of new 6-Bromoquinolin-4-ol derivatives (<b>3a</b>–<b>3h</b>) by Chan–Lam coupling utilizing different types of solvents (protic, aprotic, and mixed solvents) and bases was studied in the present manuscript. Furthermore, their potential against ESBL producing <i>Escherichia coli</i> (ESBL <i>E. coli</i>) and methicillin-resistant <i>Staphylococcus</i><i>aureus</i> (MRSA) were investigated. Commercially available 6-bromoquinolin-4-ol (<b>3a</b>) was reacted with different types of aryl boronic acids along with Cu(OAc)<sub>2</sub> via Chan–Lam coupling methodology utilizing the protic and aprotic and mixed solvents. The molecules (<b>3a</b>–<b>3h</b>) exhibited very good yields with methanol, moderate yields with DMF, and low yields with ethanol solvents, while the mixed solvent CH<sub>3</sub>OH/H<sub>2</sub>O (8:1) gave more excellent results as compared to the other solvents. The in vitro antiseptic values against ESBL <i>E. coli</i> and MRSA were calculated at five different deliberations (<b>10</b>, <b>20</b>, <b>30</b>, <b>40</b>, <b>50</b> mg/well) by agar well diffusion method. The molecule <b>3e</b> depicted highest antibacterial activity while compounds <b>3b</b> and <b>3d</b> showed low antibacterial activity. Additionally, MIC and MBC standards were calculated against the established bacteria by broth dilution method. Furthermore, a molecular docking investigation of the derivatives (<b>3a</b>–<b>3h</b>) were performed. Compound (<b>3e</b>) was highly active and depicted the least binding energy of −5.4. Moreover, to investigate the essential structural and physical properties, the density functional theory (DFT) findings of the synthesized molecules were accomplished by using the basic set PBE0-D3BJ/def2-TZVP/SMD water level of the theory. The synthesized compounds showed an energy gap from 4.93 to 5.07 eV. |
| first_indexed | 2024-03-09T22:55:49Z |
| format | Article |
| id | doaj.art-0b02caf2268c44b59bc2e303072dd12b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T22:55:49Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0b02caf2268c44b59bc2e303072dd12b2023-11-23T18:10:18ZengMDPI AGMolecules1420-30492022-06-012712373210.3390/molecules27123732Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing <i>Escherichia coli</i> and MRSA, Docking Studies, and Structural Features Determination through Computational ApproachMahwish Arshad0Nasir Rasool1Muhammad Usman Qamar2Syed Adnan Ali Shah3Zainul Amiruddin Zakaria4Department of Chemistry, Government College, University Faisalabad, Faisalabad 38000, PakistanDepartment of Chemistry, Government College, University Faisalabad, Faisalabad 38000, PakistanDepartment of Microbiology, Government College University, Faisalabad 38000, PakistanFaculty of Pharmacy, Universiti Teknologi MARA Cawangan Selangor Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, MalaysiaDepartment of Biomedical Sciences, Faculty of Medicine and Health Sciences, Universiti Malaysia Sabah, Jalan UMS, Kota Kinabalu 88400, Sabah, MalaysiaThe synthesis of new 6-Bromoquinolin-4-ol derivatives (<b>3a</b>–<b>3h</b>) by Chan–Lam coupling utilizing different types of solvents (protic, aprotic, and mixed solvents) and bases was studied in the present manuscript. Furthermore, their potential against ESBL producing <i>Escherichia coli</i> (ESBL <i>E. coli</i>) and methicillin-resistant <i>Staphylococcus</i><i>aureus</i> (MRSA) were investigated. Commercially available 6-bromoquinolin-4-ol (<b>3a</b>) was reacted with different types of aryl boronic acids along with Cu(OAc)<sub>2</sub> via Chan–Lam coupling methodology utilizing the protic and aprotic and mixed solvents. The molecules (<b>3a</b>–<b>3h</b>) exhibited very good yields with methanol, moderate yields with DMF, and low yields with ethanol solvents, while the mixed solvent CH<sub>3</sub>OH/H<sub>2</sub>O (8:1) gave more excellent results as compared to the other solvents. The in vitro antiseptic values against ESBL <i>E. coli</i> and MRSA were calculated at five different deliberations (<b>10</b>, <b>20</b>, <b>30</b>, <b>40</b>, <b>50</b> mg/well) by agar well diffusion method. The molecule <b>3e</b> depicted highest antibacterial activity while compounds <b>3b</b> and <b>3d</b> showed low antibacterial activity. Additionally, MIC and MBC standards were calculated against the established bacteria by broth dilution method. Furthermore, a molecular docking investigation of the derivatives (<b>3a</b>–<b>3h</b>) were performed. Compound (<b>3e</b>) was highly active and depicted the least binding energy of −5.4. Moreover, to investigate the essential structural and physical properties, the density functional theory (DFT) findings of the synthesized molecules were accomplished by using the basic set PBE0-D3BJ/def2-TZVP/SMD water level of the theory. The synthesized compounds showed an energy gap from 4.93 to 5.07 eV.https://www.mdpi.com/1420-3049/27/12/37324-methyl phenylboronic acidChan–Lam couplingantibacterial activitymolecular dockingNLO properties<sup>1</sup>H NMR comparison |
| spellingShingle | Mahwish Arshad Nasir Rasool Muhammad Usman Qamar Syed Adnan Ali Shah Zainul Amiruddin Zakaria Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing <i>Escherichia coli</i> and MRSA, Docking Studies, and Structural Features Determination through Computational Approach Molecules 4-methyl phenylboronic acid Chan–Lam coupling antibacterial activity molecular docking NLO properties <sup>1</sup>H NMR comparison |
| title | Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing <i>Escherichia coli</i> and MRSA, Docking Studies, and Structural Features Determination through Computational Approach |
| title_full | Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing <i>Escherichia coli</i> and MRSA, Docking Studies, and Structural Features Determination through Computational Approach |
| title_fullStr | Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing <i>Escherichia coli</i> and MRSA, Docking Studies, and Structural Features Determination through Computational Approach |
| title_full_unstemmed | Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing <i>Escherichia coli</i> and MRSA, Docking Studies, and Structural Features Determination through Computational Approach |
| title_short | Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL Producing <i>Escherichia coli</i> and MRSA, Docking Studies, and Structural Features Determination through Computational Approach |
| title_sort | facile synthesis of functionalized phenoxy quinolines antibacterial activities against esbl producing i escherichia coli i and mrsa docking studies and structural features determination through computational approach |
| topic | 4-methyl phenylboronic acid Chan–Lam coupling antibacterial activity molecular docking NLO properties <sup>1</sup>H NMR comparison |
| url | https://www.mdpi.com/1420-3049/27/12/3732 |
| work_keys_str_mv | AT mahwisharshad facilesynthesisoffunctionalizedphenoxyquinolinesantibacterialactivitiesagainstesblproducingiescherichiacoliiandmrsadockingstudiesandstructuralfeaturesdeterminationthroughcomputationalapproach AT nasirrasool facilesynthesisoffunctionalizedphenoxyquinolinesantibacterialactivitiesagainstesblproducingiescherichiacoliiandmrsadockingstudiesandstructuralfeaturesdeterminationthroughcomputationalapproach AT muhammadusmanqamar facilesynthesisoffunctionalizedphenoxyquinolinesantibacterialactivitiesagainstesblproducingiescherichiacoliiandmrsadockingstudiesandstructuralfeaturesdeterminationthroughcomputationalapproach AT syedadnanalishah facilesynthesisoffunctionalizedphenoxyquinolinesantibacterialactivitiesagainstesblproducingiescherichiacoliiandmrsadockingstudiesandstructuralfeaturesdeterminationthroughcomputationalapproach AT zainulamiruddinzakaria facilesynthesisoffunctionalizedphenoxyquinolinesantibacterialactivitiesagainstesblproducingiescherichiacoliiandmrsadockingstudiesandstructuralfeaturesdeterminationthroughcomputationalapproach |