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Molecules 2015, 20(11), 19914-19928; doi:10.3390/molecules201119661

Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties

1
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
2
Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, Abbottabad 22060, Pakistan
3
Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur 63000, Pakistan
4
The Patent Office, Karachi 74200, Pakistan
5
Department of Pharmaceutical and Biomedical Sciences, University of Salerno, Via Ponte don Melillo, Fisciano (Salerno) I-84084, Italy
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 19 August 2015 / Revised: 15 October 2015 / Accepted: 23 October 2015 / Published: 5 November 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [3817 KB, uploaded 5 November 2015]   |  

Abstract

A variety of novel 5-aryl thiophenes 4ag 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 4ag 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 4af also exhibited very good inhibition against urease enzyme. View Full-Text
Keywords: sulfacetamide; Suzuki cross coupling reactions; urease activity; antibacterial activity; DFT; frontier molecular orbitals (FMOs) analysis; MEP; hyperpolarizability and non-linear optical (NLO) properties sulfacetamide; Suzuki cross coupling reactions; urease activity; antibacterial activity; DFT; frontier molecular orbitals (FMOs) analysis; MEP; hyperpolarizability and non-linear optical (NLO) properties
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Noreen, M.; Rasool, N.; Gull, Y.; Zubair, M.; Mahmood, T.; Ayub, K.; Nasim, F.-U.-H.; Yaqoob, A.; Zia-Ul-Haq, M.; de Feo, V. Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties. Molecules 2015, 20, 19914-19928.

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