Abstract
We synthesized a series of compounds bearing pharmacologically important 1,3,4-oxadiazole and piperidine moieties. Spectral data analysis by 1H-NMR, 13C-NMR, IR and EI-MS was used to elucidate the structures of the synthesized molecules. Docking studies explained the different types of interaction of the compounds with amino acids, while bovine serum albumin (BSA) binding interactions showed their pharmacological effectiveness. Antibacterial screening of these compounds demonstrated moderate to strong activity against Salmonella typhi and Bacillus subtilis but only weak to moderate activity against the other three bacterial strains tested. Seven compounds were the most active members as acetyl cholinesterase inhibitors. All the compounds presented displayed strong inhibitory activity against urease. Compounds 7l, 7m, 7n, 7o, 7p, 7r, 7u, 7v, 7x and 7v were highly active, with respective IC50 values of 2.14±0.003, 0.63±0.001, 2.17±0.006, 1.13±0.003, 1.21±0.005, 6.28±0.003, 2.39±0.005, 2.15±0.002, 2.26±0.003 and 2.14±0.002 µM, compared to thiourea, used as the reference standard (IC50 = 21.25±0.15 µM). These new urease inhibitors could replace existing drugs after their evaluation in comprehensive in vivo studies.
Highlights
Javed Iqbal, Aziz-ur-Rehman, Muhammad Athar Abbasi, Sabahat Zahra Siddiqui, Shahid Rasool, Muhammad Ashraf, Ambar Iqbal, Sujhla Hamid, Tahir Ali Chohan, Hira Khalid, Sabina Jhaumeer Laulloo, Syed Adnan Ali Shah of this nucleus have been evaluated via the synthesis of a number of piperidine derivatives (Sanchez-Sancho, Herrandón, 1998)
The bacterial strains taken into account were Salmonella Typhi, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis, which are involved in enteric fever (Bhattacharya, Das, Choudhury, 2011), food poisoning (Vogt, Dippold, 2005), chronic infection (Pressler et al, 2011), pathogen adherence to extracellular matrix or plasma proteins (Harris, Foster, Richards, 2002) and skin allergy or hypersensitivity (Barbe et al, 2009), respectively
Computational and bovine serum albumin (BSA) binding studies were carried out to see the interaction of synthesized compounds with amino acid residues and binding capacity with this specific protein, respectively
Summary
Javed Iqbal, Aziz-ur-Rehman, Muhammad Athar Abbasi, Sabahat Zahra Siddiqui, Shahid Rasool, Muhammad Ashraf, Ambar Iqbal, Sujhla Hamid, Tahir Ali Chohan, Hira Khalid, Sabina Jhaumeer Laulloo, Syed Adnan Ali Shah of this nucleus have been evaluated via the synthesis of a number of piperidine derivatives (Sanchez-Sancho, Herrandón, 1998). The synthesized compounds were evaluated for antibacterial activity, enzyme inhibitory activity (acetylcholinesterase (AChE) and urease) and bovine serum albumin (BSA) binding. Chemists and pharmacologists have been working extensively on the synthesis of new molecules to combat and control various diseases. In this regard, two heterocyclic cores, 1,3,4-oxadiazole and piperidine, and the sulfamoyl functionality of sulfonamides have been introduced as bioactive structures. The notable pharmacological behavior of these three functionalities prompted us to synthesize some new molecules bearing all these three moieties. As an extension of our previous work (Nafeesa et al, 2015), the synthesized compounds were evaluated for their pharmacological potential as antibacterial agents and AChE and urease inhibitors
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