The Biological Potential and Synthetic Diversity of 1,3,4-Oxadiazole Multiplexed with Various Heterocyclic Compounds

Year 2023, Volume: 10 Issue: 2, 267 - 276, 31.05.2023

Rahul K , Deevan Paul Amarnath , Hariraj Narayanan , Adhya Das

https://doi.org/10.18596/jotcsa.1202640

Cited By: 2

Abstract

Countless bioactive compounds are having the oxadiazole nucleus showing clinical and biological applications. Oxadiazole is a heterocyclic compound of the azole family that has gained increasing attention due to its wide therapeutic potential. Many significant synthetic medicinal compounds have the oxadiazole scaffold, which provided a good treatment idea and binds with high affinity to a variety of receptors to aid in the development of novel beneficial derivatives. Numerous researchers have worked to create novel oxadiazole compounds and evaluate them for how they affect inflammation, tumor, epilepsy, microbial infections, and analgesic properties. The present review article summarizes some of the oxadiazole derivatives synthesized and their biological activities and can be a useful guide for researchers working on this scaffold.

Keywords

heterocyclic scaffolds, 1.3.4-oxadiazole, anticonvulsant, anti-inflammatory, antimicrobial, anticholinesterase

Thanks

Authors are thankful to Chettinad Academy of Research and Education for infrastructure support and CARE seed money research grant (Ref.No.004/Regr./AR-Research/2022-02)

References

• 1. Qadir T, Amin A, Sharma PK, Jeelani I, Abe H. A Review on Medicinally Important Heterocyclic Compounds. Open Med Chem J. 2022;16(1):1–34.
• 2. Siwach A, Verma PK. Therapeutic potential of oxadiazole or furadiazole containing compounds. BMC Chem [Internet]. 2020;14(1):1–40. Available from: https://doi.org/10.1186/s13065-020-00721-2
• 3. Shukla C, Srivastav S. Biologically Active Oxadiazole. Asian J Res Pharm Sci. 2015;5(4):227.
• 4. Khalilullah H, J. Ahsan M, Hedaitullah M, Khan S, Ahmed B. 1,3,4-Oxadiazole: A Biologically Active Scaffold. Mini-Reviews Med Chem. 2012;12(8):789–801.
• 5. Xie Y, Yang W, Chen X, Xiao J. Inhibition of flavonoids on acetylcholine esterase: Binding and structure–activity relationship. Food Funct. 2014 Sep 24;5(10):2582–9.
• 6. Chawla G, Naaz B, Siddiqui AA. Exploring 1,3,4-Oxadiazole Scaffold for Anti-inflammatory and Analgesic Activities: A Review of Literature From 2005-2016. Mini-Reviews Med Chem. 2017 Feb 23;18(3).
• 7. Peraman R, Varma RV, Reddy YP. Re-engineering nalidixic acid’s chemical scaffold: A step towards the development of novel anti-tubercular and anti-bacterial leads for resistant pathogens. Bioorganic Med Chem Lett. 2015 Oct 1;25(19):4314–9.
• 8. Jang C, Yadav DK, Subedi L, Venkatesan R, Venkanna A, Afzal S, et al. Identification of novel acetylcholinesterase inhibitors designed by pharmacophore-based virtual screening, molecular docking and bioassay. Sci Rep. 2018 Dec 1;8(1).
• 9. Bhat MA, Al-Omar MA, Siddiqui N. Synthesis, anticonvulsant and neurotoxicity of some novel 1,3,4-oxadiazole derivatives of phthalimide. Der Pharma Chem [Internet]. 2010;2(2):1–10. Available from: www.derpharmachemica.com
• 10. Shingare RM, Patil YS, Sangshetti JN, Patil RB, Rajani DP, Madje BR. Synthesis, biological evaluation and docking study of some novel isoxazole clubbed 1,3,4-oxadiazoles derivatives. Med Chem Res [Internet]. 2018;27(4):1283–91. Available from: http://dx.doi.org/10.1007/s00044-018-2148-2
• 11. Alghamdi AA, Alam MM, Nazreen S. In silico ADME predictions and in vitro antibacterial evaluation of 2-hydroxy benzothiazole-based 1,3,4-oxadiazole derivatives. Turkish J Chem. 2020;44(4):1068–84.
• 12. George N, Sabahi B Al, AbuKhader M, Balushi K Al, Akhtar MJ, Khan SA. Design, synthesis and in vitro biological activities of coumarin linked 1,3,4-oxadiazole hybrids as potential multi-target directed anti-Alzheimer agents. J King Saud Univ - Sci. 2022 Jun 1;34(4).
• 13. Colovic MB, Krstic DZ, Lazarevic-Pasti TD, Bondzic AM, Vasic VM. Acetylcholinesterase Inhibitors: Pharmacology and Toxicology. Curr Neuropharmacol. 2013;11(3):315–35.
• 14. Kumari P, Tripathi A, Kumar M, Seth A, Kumar S. Bioorganic Chemistry diazole as multitargeted hybrids for the treatment of Alzheimer ’ s disease. 2021;111(April).
• 15. Dhanjal JK, Sharma S, Grover A, Das A. Use of ligand-based pharmacophore modeling and docking approach to find novel acetylcholinesterase inhibitors for treating Alzheimer’s. Biomed Pharmacother. 2015 Apr 1;71:146–52.
• 16. Mishra P, Sharma P, Tripathi PN, Gupta SK, Srivastava P, Seth A, et al. Design and development of 1,3,4-oxadiazole derivatives as potential inhibitors of acetylcholinesterase to ameliorate scopolamine-induced cognitive dysfunctions. Bioorg Chem [Internet]. 2019;89:103025. Available from: https://doi.org/10.1016/j.bioorg.2019.103025
• 17. Kumar Singh A, Lohani M, Parthsarthy R. Synthesis , Characterization and Anti-Inflammatory Activity of Various Isatin Derivatives. Iran J Pharm Res [Internet]. 2013;12(2):319–23. Available from: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3813233/
• 18. Tomasz G. New 1 , 3 , 4-Oxadiazole Derivatives of Pyridothiazine- 1 , 1-Dioxide with Anti-Inflammatory Activity. Int J Mol Sci. 2020;21:1–22.
• 19. Grover J, Bhatt N, Kumar V, Patel NK, Gondaliya BJ, Elizabeth Sobhia M, et al. 2,5-Diaryl-1,3,4-oxadiazoles as selective COX-2 inhibitors and anti-inflammatory agents. RSC Adv [Internet]. 2015;5(56):45535–44. Available from: http://dx.doi.org/10.1039/C5RA01428J
• 20. Bhardwaj S, Parashar B, Parashar N, Sharma VK. Microwave assisted synthesis and pharmacological evaluation of. Arch Appl Sci Res [Internet]. 2011;3(2):558–67. Available from: www.scholarsresearchlibrary.com
• 21. Banik BK, Sahoo BM, Kumar BVVR, Panda KC, Jena J, Mahapatra MK, et al. Green synthetic approach: An efficient eco-friendly tool for synthesis of biologically active oxadiazole derivatives. Molecules. 2021;26(4).
• 22. Singh RB, Singh GK, Chaturvedi K, Kumar D, Singh SK, Zaman MK. Design, synthesis, characterization, and molecular modeling studies of novel oxadiazole derivatives of nipecotic acid as potential anticonvulsant and antidepressant agents. Med Chem Res [Internet]. 2018;27(1):137–52. Available from: http://dx.doi.org/10.1007/s00044-017-2047-y
• 23. Wang S, Liu H, Wang X, Lei K, Li G, Li J, et al. Synthesis of 1,3,4-oxadiazole derivatives with anticonvulsant activity and their binding to the GABAA receptor. Eur J Med Chem [Internet]. 2020;206:112672. Available from: https://doi.org/10.1016/j.ejmech.2020.112672
• 24. Rajak H, Singour P, Kharya MD, Mishra P. A Novel Series of 2,5-Disubstituted 1,3,4-oxadiazoles: Synthesis and SAR Study for their Anticonvulsant Activity. Vol. 77, Chemical Biology and Drug Design. 2011. p. 152–8.
• 25. Mickevičius V, Vaickelionienė R, Sapijanskaitė B. Synthesis of substituted 1,3,4-oxadiazole derivatives. Chem Heterocycl Compd. 2009;45(2):215–8.
• 26. Nazari M, Rezaee E, Hariri R, Akbarzadeh T, Tabatabai SA. Novel 1,2,4-oxadiazole derivatives as selective butyrylcholinesterase inhibitors: Design, synthesis, and biological evaluation. EXCLI J. 2021;20:907–21.
• 27. Pflégr V, Štěpánková Š, Svrčková K, Švarcová M, Vinšová J, Krátký M. 5-Aryl-1,3,4-Oxadiazol-2-Amines Decorated with Long Alkyl and Their Analogues: Synthesis, Acetyl-and Butyrylcholinesterase Inhibition and Docking Study. Pharmaceuticals. 2022;15(4):1–21.
• 28. Ergenç N, Çapan G, Demirdamar R. Synthesis, characterization and analgesic activity of new 4-arylhydrazono-3-methoxymethyl-2-pyrazolin-5-ones. Arzneimittel-Forschung/Drug Res. 2001;51(2):118–24.
• 29. Vaidya A, Pathak D, Shah K. 1,3,4-oxadiazole and its derivatives: A review on recent progress in anticancer activities. Chem Biol Drug Des. 2021 Mar 1;97(3):572–91.
• 30. Parikh PK, Marvaniya HM, Sen DJ. Synthesis and biological evaluation of 1,3,4-oxadiazole derivatives as potential antibacterial and antifungal agents. Int J Drug Dev Res [Internet]. 2011;3(2):248–55. Available from: http://www.ijddr.in
• 31. Misra HK. Synthesis of Some New Substituted 1,3,4‐Oxadiazoles as Potential Insecticidal, Antibacterial and Anti‐acetylcholine Esterase Agents. Arch Pharm (Weinheim). 1983;316(6):487–93.