Synthesis and urease inhibitory potential of benzophenone sulfonamide hybrid in vitro and in silico. Issue 6 (15th March 2019)

• Record Type: Journal Article
• Authors: Arshia, ; Begum, Farida; Almandil, Noor Barak; Lodhi, Muhammad Arif; Khan, Khalid Mohammed; Hameed, Abdul; Perveen, Shahnaz
• Is Part Of: Bioorganic & medicinal chemistry. Volume 27:Issue 6(2019)
• Page Start: 1009
• Page End: 1022
• Publication Date: 2019-03-15
• Subjects: Benzophenone sulfonamide hybrid -- Urease -- In vitro -- In silico; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2019.01.043
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Highlights: Syntheses of benzophenone sulfonamide analogs have been carried out. Structures of all synthetic compounds were elucidated by spectroscopic techniques. Urease inhibitory activity of synthetic compounds has been carried out. In silico studies of active analogs have been performed. Structure-activity relationship has been evaluated. Abstract: This study deals with the synthesis of benzophenone sulfonamides hybrids (1 –31 ) and screening against urease enzyme in vitro . Studies showed that several synthetic compounds were found to have good urease enzyme inhibitory activity. Compounds1 ( N ′-((4′-hydroxyphenyl)(phenyl)methylene)-4′′-nitrobenzenesulfonohydrazide), 2 ( N ′-((4′-hydroxyphenyl)(phenyl)methylene)-3′′-nitrobenzenesulfonohydrazide), 3 ( N ′-((4′-hydroxyphenyl)(phenyl)methylene)-4′′-methoxybenzenesulfonohydrazide), 4 (3′′, 5′′-dichloro-2′′-hydroxy- N ′-((4′-hydroxyphenyl)(phenyl)methylene)benzenesulfonohydrazide), 6 (2′′, 4′′-dichloro- N ′-((4′-hydroxyphenyl)(phenyl)methylene)benzenesulfonohydrazide), 8 (5-(dimethylamino)- N ′-((4-hydroxyphenyl)(phenyl)methylene)naphthalene-1-sulfono hydrazide), 10 (2′′-chloro- N ′-((4′-hydroxyphenyl)(phenyl)methylene)benzenesulfonohydrazide), 12 ( N ′-((4′-hydroxyphenyl)(phenyl)methylene)benzenesulfonohydrazide) have found to be potently active having an IC50 value in the range of 3.90–17.99 µM. These compounds showed superior activity than standard acetohydroxamic acid (IC50 = 29.20 ± 1.01 µM). Moreover, in silico studies on most active compounds were also performed to understand the binding interaction of most active compounds with active sites of urease enzyme. Structures of all the synthetic compounds were elucidated by 1 H NMR, 13 C NMR, EI-MS and FAB-MS spectroscopic techniques.