Synthesis, urease inhibition screening and molecular docking studies of piperonal based imine derivatives
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Medicinal Chemistry Research https://doi.org/10.1007/s00044-020-02651-z
ORIGINAL RESEARCH
Synthesis, urease inhibition screening and molecular docking studies of piperonal based imine derivatives Obaid-ur-Rahman Abid 1 Saima Daud1 Asma Sardar1 Wajid Rehman1 Abdul Wadood2 Ashfaq Ur Rehman2,3 Toheed Akhter4,5 Iram Bibi1 Zaheer Ahmad6 Muhammad Yasir1 ●
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Received: 7 May 2020 / Accepted: 8 October 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract A series of piperonal-based imines (3a–c) and bis-imines (5a-o) have been synthesized in search of new urease inhibitors. Synthesized compounds were characterized by 1H NMR, 13C NMR and EI-MS. These derivatives were subjected to evaluation of urease inhibitory potential, which exhibited a varied degree of potential, ranging from 41.7 ± 5.8 to 353.6 ± 5.8 µM, when compared with the standard inhibitor (i.e., thiourea having IC50 value 21.8 ± 1.51 µM). Amongst the synthesized bis-imines, three compounds 5d, 5h, and 5g exhibited good inhibitory potential having IC50 values 41.7 ± 5.8, 43.7 ± 5.8, and 52.6 ± 5.8 respectively so can be further investigated. The remaining compounds exhibited moderate to weak activities. Molecular modeling studies were performed to understand the binding interactions with the enzyme. Keywords Piperonal Diamines bis-imines Urease inhibition Molecular modeling studies ●
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Introduction Urease is a Ni-containing metalloenzyme that is extensively distributed in varieties of bacteria, algae, fungi, plants, and some invertebrates [1, 2]. It is known to speed up urea hydrolysis to ammonia (NH3) and carbon dioxide (CO2) at
Supplementary information The online version of this article (https:// doi.org/10.1007/s00044-020-02651-z) contains supplementary material, which is available to authorized users. * Obaid-ur-Rahman Abid [email protected] 1
Department of Chemistry, Hazara University, Mansehra, Pakistan
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Department of Biochemistry, Abdul Wali Khan University Mardan, Mardan 23200, Pakistan
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State Key Laboratory of Microbial Metabolism, Department of Bioinformatics and Biostatistics, National Experimental Teaching Center for Life Sciences and Biotechnology, College of Life Sciences and Biotechnology, Shanghai Jiao Tong University, Shanghai 200240, China
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Department of Chemistry, Center for Superfunctional Materials, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan 44919, Republic of Korea
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Department of Chemistry, School of Sciences, University of Management and Technology, Johar Town, C-II, Lahore, Pakistan
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Department of Chemistry, University of Wah, Wah Cantt, Pakistan
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the rate of ~1014 times the rate of the uncatalysed reactions [3]. These reactions result in the release of high ammonia concentrations, which in addition to accompanying pH elevation, put negative implications in medicinal and agricultural field [4–6]. In recent years, urease inhibitors played a significant role in the treatment of the infection
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