Synthesis and Biological Activities Evaluation of Novel Spiroheterocycles Containing 1,3,4-Oxadiazoline Moiety



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Submitted Feb 1, 2023
Published Mar 7, 2023
10.24018/ejchem.2023.4.2.127

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A novel series of spiro 3-acetyl-1,3,4-oxadiazolines were synthesized via oxidative cyclization reaction of different 2-furoyl and 2-thenoyl hydrazones with acetic anhydride. The structures of obtained compounds were confirmed by IR, MS, 1H NMR, 13C NMR and Elemental analysis methods and are in full agreement with their molecular structure. The newly synthesized spiro 1,3,4-oxadiazolines were screened for in vitro for their biological activity against a variety of bacterial strains (Euterococci, Escherichia coli, Staphylococcus aureus, Klebsiella spp, Proteus spp), and fungi (Aspergillus niger, Candida albicans), employing the nutrient agar disc diffusion method. The obtained results showed that these compounds have good inhibition against the tested pathogens.
Keywords: 2-Furoylhydrazone 2-Thenoyl-Hydrazone Oxadiazole Oxidative Cyclization Spiro-1,3,4-Oxadiazoline

References

  1. Somashekhar M, Kotnal RB. Recent advances in the application of oxadiazoles in multicomponent reactions from 2015–16: A review. Indo. Am. J. Pharm. Sci., 2018; 5: 7632–7644.
     Google Scholar
  2. Biernacki K, Da´sko M, Ciupak O, Rachon J, Demkowicz S. Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery, Pharmaceuticals, 2020, 13, 111-156.
     Google Scholar
  3. Salahuddin MA, Yar MS, Mazumder R, Chakraborthy GS, Ahsan MJ, Rahman MU. Updates on synthesis and biological activities of 1,3,4-oxadiazole: A review. Synth. Commun., 2017, 47, 1805–1847.
     Google Scholar
  4. Pitasse-Santos P, Sueth-Santiago V, Lima ME. 1,2,4-and 1, 3, 4-Oxadiazoles as Scaffolds in the Development of Antiparasitic Agents. J. Braz. Chem. Soc., 2018; 29(3): 435-456.
     Google Scholar
  5. Glomb T, Swiatek P. Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives, Int. J. Mol. Sci., 2021; 22: 6979-7002.
     Google Scholar
  6. Em PC, Tuyen TN, Nguyen DH, Duy VD, Tuoi HD. Synthesis of a Series of Novel 2-Amino-5-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole Derivatives as Potential Anticancer, Antifungal and Antibacterial Agents, Med. Chem., 2022; 18(5): 558-573.
     Google Scholar
  7. Kiran S. 1,3,4-oxadiazole a potent drug candidate with various pharmacological activities, Inter. J. Pharm. Pharm. Sc., 2021; 3(3): 9-16.
     Google Scholar
  8. Siwach A, Verma PK. Therapeutic potential of oxadiazole or furadiazole containing compounds. BMC Chem., 2020;14(1): 70-79.
     Google Scholar
  9. Hicks C, Gulick RM. Raltegravir: The First HIV Type 1 Integrase Inhibitor. Clin. Infect. Dise., 2009; 48(7): 931-939.
     Google Scholar
  10. Abu-Zaied MA, Nawwar GA, Swellem RH, El-Sayed SH. Synthesis and Screening of New 5-Substituted-1,3,4-oxadiazole-2-thioglycosides as Potent Anticancer Agents, Pharmacol. & Pharm., 2012; 3: 254-261.
     Google Scholar
  11. Wang J-J, Sun W, Jia W-D, Bian M, Yu L-J. Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and1,2,4-oxadiazole derivatives: a mini review, J. Enz. Inh. Med. Chem., 2022; 37: 1, 2304–2319.
     Google Scholar
  12. Aiswarya G, Divekar K. A Review on Synthesis of Various Oxadiazole Derivatives Applying Green Chemistry Methods Der Pharm. Lett., 2021; 13(7): 108-131.
     Google Scholar
  13. Singh R, Bhardwaj D, Saini MR. Recent advancement in the synthesis of diverse spiroindeno[1,2-b]quinoxalines: a review, RSC Adv., 2021; 11: 4760-4804.
     Google Scholar
  14. Alizadeh A, Moafi, L. Simple access to spirooxadiazole compounds containing a quinoxaline moiety using a nitrile imine intermediate generated in situ, Heterocycl. Commun., 2017; 23: 375–378.
     Google Scholar
  15. Wang H, Pan, B, Zhang, W, Yang, C, Liu, X, Zhao, Z, et al. A facile and efficient synthesis of polycyclic spiropyrrolidine oxindoles bearing mesityl oxide unit via a three-component 1,3-dipolar cycloaddition reaction. Tetrahedron, 2015; 71: 8131–8139.
     Google Scholar
  16. Dadiboyena S, Valente EJ, Hamme AT. A novel synthesis of 1,3,5-trisubstituted pyrazoles through a spiro-pyrazoline intermediate via a tandem 1,3-dipolar cycloaddition/elimination. Tetrahedron Lett., 2009; 50: 291-294.
     Google Scholar
  17. Othman AA, Kihel M, Amara S. 1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antibacterial agents, Arab. J. Chem., 2019; 12: 1660-1675.
     Google Scholar
  18. El-Gazzar AB, Scholten K, Guo Y, Weibenbach K, Hitzler MG, Roth G, et al. Cycloadditions of 1-aza-2-azoniaallene cations to isothiocyanates. J. Chem. Soc. Perkin Trans. 1999; 1: 1999-2010.
     Google Scholar
  19. Okimoto M, Chiba T. Electrochemical oxidation of ketone acylhydrazones and their hydrogen cyanide adducts in sodium cyanide-methanol. Transformation of ketones to nitriles, J. Org. Chem., 1990; 55(3): 1070-1076.
     Google Scholar
  20. Yavari I, Askarian-Amiri M, Taheri Z. A convenient synthesis of spiro-indolo[2,1 b]quinazol-ine 6,2′ [1,3,4] oxadiazoles from tryptanthrin and nitrile imines, Monatshefte für Chemie – Chem. Month., 2019; 150: 1093–1099.
     Google Scholar
  21. Morjan RY, Ghonium FJ, Abu-Teim OS, Awadallah AM, Al-Reefi MR, Elmanama A, et al. Syntheses of N-acylhydrazones of 2-hydroxy-3,5-dinitrobenzohydrazide, and their Conversion into 3-Acetyl-2,3-dihydro-1,3,4-oxadiazole. IUG J.Nat. Stud., 2022; 30(02): 38-46.
     Google Scholar
  22. Manika M, Chanotiya C, Darokar M, Singh S, Bagchi G. Compositional characters and antimicrobial potential of Artemisia stricta Edgew. f. stricta Pamp. Essential oil. Rec. Nat. Prod., 2016; 10: 40-46.
     Google Scholar
  23. Methods for dilution antimicrobial susceptibility tests for bacteria grow aerobically. Approved Standard M7-A4. Clinical and Laboratory Standards Institute, Wayne, Pa, USA, 2005.
     Google Scholar