Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties
A variety of novel 5-aryl thiophenes 4a–g containing sulphonylacetamide (sulfacetamide) groups were synthesized in appreciable yields via Pd[0] Suzuki cross coupling reactions. The structures of these newly synthesized compounds were determined using spectral data and elemental analysis. Density fun...
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MDPI AG
2015-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/11/19661 |
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| author | Mnaza Noreen Nasir Rasool Yasmeen Gull Muhammad Zubair Tariq Mahmood Khurshid Ayub Faiz-ul-Hassan Nasim Asma Yaqoob Muhammad Zia-Ul-Haq Vincenzo de Feo |
| author_facet | Mnaza Noreen Nasir Rasool Yasmeen Gull Muhammad Zubair Tariq Mahmood Khurshid Ayub Faiz-ul-Hassan Nasim Asma Yaqoob Muhammad Zia-Ul-Haq Vincenzo de Feo |
| author_sort | Mnaza Noreen |
| collection | DOAJ |
| description | A variety of novel 5-aryl thiophenes 4a–g containing sulphonylacetamide (sulfacetamide) groups were synthesized in appreciable yields via Pd[0] Suzuki cross coupling reactions. The structures of these newly synthesized compounds were determined using spectral data and elemental analysis. Density functional theory (DFT) studies were performed using the B3LYP/6-31G (d, p) basis set to gain insight into their structural properties. Frontier molecular orbital (FMOs) analysis of all compounds 4a–g was computed at the same level of theory to get an idea about their kinetic stability. The molecular electrostatic potential (MEP) mapping over the entire stabilized geometries of the molecules indicated the reactive sites. First hyperpolarizability analysis (nonlinear optical response) were simulated at the B3LYP/6-31G (d, p) level of theory as well. The compounds were further evaluated for their promising antibacterial and anti-urease activities. In this case, the antibacterial activities were estimated by the agar well diffusion method, whereas the anti-urease activities of these compounds were determined using the indophenol method by quantifying the evolved ammonia produced. The results revealed that all the sulfacetamide derivatives displayed antibacterial activity against Bacillus subtiles, Escherichia coli, Staphylococcus aureus, Shigella dysenteriae, Salmonella typhae, Pseudomonas aeruginosa at various concentrations. Furthermore, the compound 4g N-((5-(4-chlorophenyl)thiophen-2-yl)sulfonyl) acetamide showed excellent urease inhibition with percentage inhibition activity ~46.23 ± 0.11 at 15 µg/mL with IC50 17.1 µg/mL. Moreover, some other compounds 4a–f also exhibited very good inhibition against urease enzyme. |
| first_indexed | 2024-12-11T16:42:47Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T16:42:47Z |
| publishDate | 2015-11-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a1b714de3ad04da9a481a41940030fa62022-12-22T00:58:17ZengMDPI AGMolecules1420-30492015-11-012011199141992810.3390/molecules201119661molecules201119661Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide MoietiesMnaza Noreen0Nasir Rasool1Yasmeen Gull2Muhammad Zubair3Tariq Mahmood4Khurshid Ayub5Faiz-ul-Hassan Nasim6Asma Yaqoob7Muhammad Zia-Ul-Haq8Vincenzo de Feo9Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, PakistanDepartment of Chemistry, Government College University Faisalabad, Faisalabad 38000, PakistanDepartment of Chemistry, Government College University Faisalabad, Faisalabad 38000, PakistanDepartment of Chemistry, Government College University Faisalabad, Faisalabad 38000, PakistanDepartment of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, Abbottabad 22060, PakistanDepartment of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, Abbottabad 22060, PakistanDepartment of Chemistry, The Islamia University of Bahawalpur, Bahawalpur 63000, PakistanDepartment of Chemistry, The Islamia University of Bahawalpur, Bahawalpur 63000, PakistanThe Patent Office, Karachi 74200, PakistanDepartment of Pharmaceutical and Biomedical Sciences, University of Salerno, Via Ponte don Melillo, Fisciano (Salerno) I-84084, ItalyA variety of novel 5-aryl thiophenes 4a–g containing sulphonylacetamide (sulfacetamide) groups were synthesized in appreciable yields via Pd[0] Suzuki cross coupling reactions. The structures of these newly synthesized compounds were determined using spectral data and elemental analysis. Density functional theory (DFT) studies were performed using the B3LYP/6-31G (d, p) basis set to gain insight into their structural properties. Frontier molecular orbital (FMOs) analysis of all compounds 4a–g was computed at the same level of theory to get an idea about their kinetic stability. The molecular electrostatic potential (MEP) mapping over the entire stabilized geometries of the molecules indicated the reactive sites. First hyperpolarizability analysis (nonlinear optical response) were simulated at the B3LYP/6-31G (d, p) level of theory as well. The compounds were further evaluated for their promising antibacterial and anti-urease activities. In this case, the antibacterial activities were estimated by the agar well diffusion method, whereas the anti-urease activities of these compounds were determined using the indophenol method by quantifying the evolved ammonia produced. The results revealed that all the sulfacetamide derivatives displayed antibacterial activity against Bacillus subtiles, Escherichia coli, Staphylococcus aureus, Shigella dysenteriae, Salmonella typhae, Pseudomonas aeruginosa at various concentrations. Furthermore, the compound 4g N-((5-(4-chlorophenyl)thiophen-2-yl)sulfonyl) acetamide showed excellent urease inhibition with percentage inhibition activity ~46.23 ± 0.11 at 15 µg/mL with IC50 17.1 µg/mL. Moreover, some other compounds 4a–f also exhibited very good inhibition against urease enzyme.http://www.mdpi.com/1420-3049/20/11/19661sulfacetamideSuzuki cross coupling reactionsurease activityantibacterial activityDFTfrontier molecular orbitals (FMOs) analysisMEPhyperpolarizability and non-linear optical (NLO) properties |
| spellingShingle | Mnaza Noreen Nasir Rasool Yasmeen Gull Muhammad Zubair Tariq Mahmood Khurshid Ayub Faiz-ul-Hassan Nasim Asma Yaqoob Muhammad Zia-Ul-Haq Vincenzo de Feo Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties Molecules sulfacetamide Suzuki cross coupling reactions urease activity antibacterial activity DFT frontier molecular orbitals (FMOs) analysis MEP hyperpolarizability and non-linear optical (NLO) properties |
| title | Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties |
| title_full | Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties |
| title_fullStr | Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties |
| title_full_unstemmed | Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties |
| title_short | Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties |
| title_sort | synthesis density functional theory dft urease inhibition and antimicrobial activities of 5 aryl thiophenes bearing sulphonylacetamide moieties |
| topic | sulfacetamide Suzuki cross coupling reactions urease activity antibacterial activity DFT frontier molecular orbitals (FMOs) analysis MEP hyperpolarizability and non-linear optical (NLO) properties |
| url | http://www.mdpi.com/1420-3049/20/11/19661 |
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