title: Synthesis, Density Functional Theory (DFT), Urease Inhibition and Antimicrobial Activities of 5-Aryl Thiophenes Bearing Sulphonylacetamide Moieties.
abstract: 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.
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. mnazanoreen@yahoo.com.
authors.forename: Mnaza
authors.initials: M
authors.lastname: Noreen
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. nasirrasool@gcuf.edu.pk.
authors.forename: Nasir
authors.initials: N
authors.lastname: Rasool
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. yasmeenchem1@yahoo.com.
authors.forename: Yasmeen
authors.initials: Y
authors.lastname: Gull
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan. zubairmkn@yahoo.com.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Zubair
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, Abbottabad 22060, Pakistan. mahmood@ciit.net.pk.
authors.forename: Tariq
authors.initials: T
authors.lastname: Mahmood
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, Abbottabad 22060, Pakistan. khurshid@ciit.net.pk.
authors.forename: Khurshid
authors.initials: K
authors.lastname: Ayub
authors.affiliation: Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur 63000, Pakistan. faiznasim@hotmail.com.
authors.forename: Faiz-Ul-Hassan
authors.initials: FU
authors.lastname: Nasim
authors.affiliation: Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur 63000, Pakistan. asmayaqoobctn@gmail.com.
authors.forename: Asma
authors.initials: A
authors.lastname: Yaqoob
authors.affiliation: The Patent Office, Karachi 74200, Pakistan. ahirzia@gmail.com.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Zia-Ul-Haq
authors.affiliation: Department of Pharmaceutical and Biomedical Sciences, University of Salerno, Via Ponte don Melillo, Fisciano (Salerno) I-84084, Italy. defeo@unisa.it.
authors.forename: Vincenzo
authors.initials: V
authors.lastname: de Feo
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D055672:Static Electricity; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014510:Urease / Q000037:antagonists & inhibitors*
chemical_list: D000081:Acetamides; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D013876:Thiophenes; D014510:Urease
keywords: DFT; MEP; Suzuki cross coupling reactions; antibacterial activity; frontier molecular orbitals (FMOs) analysis; hyperpolarizability and non-linear optical (NLO) properties; sulfacetamide; urease activity