Abstract
1,3,4-Oxadiazole bearing compounds are one of the most attractive class for researchers due to their biological activities. In the undertaken research, a new series of 5-substituted 1,3,4-oxadiazole-2-yl-4-(piperidin-1-ylsulfonyl)benzylsulfides (6a–k) were synthesized. The synthesis was carried out by converting different organic acids sequentially into corresponding esters, hydrazides and 5-substituted-1,3,4-oxadiazole-2-thiols (4a–k). Finally, the target compounds, 6a–k were prepared by stirring 5-substituted-1,3,4-oxadiazole-2-thiols with 1-(4-(bromomethyl)phenyl sulfonyl)piperidine (5) in the presence of N,N-dimethylformamide (DMF) and sodium hydride. All the structures were elucidated by modern spectroscopic techniques. The synthesized compounds were screened against butyrylcholinesterase (BChE) enzyme and also subjected for molecular docking studies to find ligand-BChE binding affinity and ligand orientation in active sites of human BChE protein. Amino acid residues such as Gly116, His438, Tyr332 and Ser198 are found to be important common residues for binding of highlighted compounds and are likely to be involved in the ligands’ stabilization in the binding site.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Omar FA, Mahfouz NM, Rahman MA (1996) Design, synthesis and anti-inflammatory activity of some 1,3,4-oxadiazole derivatives. Eur J Med Chem 131:819–825
Goswami BN, Kataky JCS, Baruah JN (1984) Synthesis and antibacterial activity of 1-(2,4-dichlorobenzoyl)-4-substituted thiosemicarbazides, 1,2,4-triazoles and their methyl derivatives. J Heterocyclic Chem 21:1225–1229
Holla BS, Poojary KN, Kalluraya B, Gowda PV (1996) 5-Substituted-1,3,4-oxadiazolin-2-thiones. Indian J Heterocyclic Chem 5:273–276
Hasan A, Thomas NF, Gapil S (2011) Synthesis, characterization and antifungal evaluation of 5-substituted-4-amino-1,2,4-triazole-3-thioesters. Molecules 16:1297–1309
Omar MT (1997) Synthesis of new xanthenone derivatives of expected antibilharzial activity. Arch Pharm Res 20:602–609
Matsumoto K, Kawamura Y, Yasuda Y, Tanimoto T, Matsumoto K, Yoshida T, Shoji JJ (1998) Isolation and characterization of Thioxamycin. Antibiot (Tokyo) 42:1465–1469
Shafi SS, Radhakrishnan TR (1995) Synthesis and antibacterial activity of some 2,5-di-substituted-1,3,4-oxadiazole 1,3,4-thiadiazole, 1,2,4-triazole and 4-thiazolidinone. Indian J Heterocyclic Chem 5:133–138
Tan TMC, Chen Y, Kong KH, Bai J, Li Y, Lim SG, Ang TH, Lam Y (2006) Synthesis and the biological evaluation of 2-benzenesulfonylalkyl-5-substituted-sulfanyl-[1,3,4]-oxadiazoles as potential anti-hepatitis B virus agents. Antiviral Res 71:7–14
Wagle S, Adhikari AV, Kumari NS (2008) Synthesis of some new 2-(3-methyl-7-substituted-2-oxoquinoxalinyl)-5-(aryl)-1,3,4-oxadiazoles as potential non-steroidal anti-inflammatory and analgesic agents. Indian J Chem 47B:439–448
Sanchez-Sancho F, Herrandon B (1998) Short syntheses of (S)-pipecolic acid,(R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks. Tetrahedron-Asymmetry 9:1951–1965
Nithiya S, Karthik N, Jayabharathi J (2011) In vitro antioxidant activity of hindered piperidone derivatives. Int J Pharm Pharm Sci 3:254–256
Aziz-ur-Rehman FA, Abbas N, Abbasi MA, Khan KM, Ashraf M, Ahmad I, Ejaz SA (2013) Synthesis, characterization and biological screening of 5-substituted-1,3,4-oxadiazole-2yl-N-(2-methoxy-5-chlorophenyl)-2-sulfanyl acetamide. Pak J Pharm Sci 26:345–352
Aziz-ur-Rehman FA, Abbasi MA, Rasool S, Malik A, Ashraf M, Ahmad I, Ejaz SA (2013) Synthesis of new N-(5-chloro-2-methoxyphenyl)-4-(5-substituted-1,3,4-oxadiazol-2-ylthio) butanamide derivatives as suitable lipoxygenase inhibitors. J Saudi Chem Soc 20:S488–S494
Aziz-ur-Rehman NK, Abbasi MA, Khalid H, Khan KM, Ashraf M, Ahmad I, Ejaz SA (2012) Synthesis, spectral characterization and biological activity of S-substituted derivatives of 5-(4-nitrophenyl)-1,3,4-oxadiazole-2-thiol. Asian J Pharm Health Sci 3:370–376
Aziz-ur-Rehman SSZ, Abbasi MA, Abbas N, Khan KM, Shahid M, Mahmood Y, Akhtar MN, Lajis NH (2012) Synthesis, antibacterial screening and hemolytic activity of S-substituted derivatives of 5-benzyl-1,3,4-oxadiazole-2-thiol. Int J Pharm Pharm Sci 4:676–680
Ellman GL, Courtney KD, Andres V, Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmcol 7:88–95
Humphrey W, Dalke A, Schulten K (1996) VMD: visual molecular dynamics. J Mol Graph 14:33–38
Allouche AR (2010) Gabedit—A graphical user interface for computational chemistry softwares. J Comput Chem 32:174–182
Stewart JJ (2007) Optimization of parameters for semi-empirical methods. V: modification of NDDO approximations and application to 70 elements. J Mol Model 13:1173–1213
Trott O, Olson AJ (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 31:455–461
Primožič I, Hrenar T, Tomić S (2012) Binding modes of quinuclidinium esters to butyrylcholinesterase. Croat Chem Acta:8577–8583
Özturan Özer E, Tan OU, Ozadali K, Küçükkılınç T, Balkan A, Uçar G (2013) Synthesis, molecular modeling and evaluation of novel N′-2-(4-benzylpiperidin-/piperazin-1-yl)acylhydrazone derivatives as dual inhibitors for cholinesterases and Aβ aggregation. Bioorg Med Chem Lett 23:440–443
Acknowledgement
The authors are thankful to the Higher Education Commission of Pakistan for the financial support regarding this research work and the spectroscopic analysis.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2018 Springer International Publishing AG
About this paper
Cite this paper
Khalid, H. et al. (2018). Synthesis, Spectral Analysis and Biological Evaluation of 5-Substituted 1,3,4-Oxadiazole-2-yl-4-(Piperidin-1-ylsulfonyl)Benzyl Sulfide. In: Ramasami, P., Gupta Bhowon, M., Jhaumeer Laulloo, S., Li Kam Wah, H. (eds) Emerging Trends in Chemical Sciences. ICPAC 2016. Springer, Cham. https://doi.org/10.1007/978-3-319-60408-4_14
Download citation
DOI: https://doi.org/10.1007/978-3-319-60408-4_14
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-60407-7
Online ISBN: 978-3-319-60408-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)