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

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  •   Hany M. Dalloul

  •   Kholoud R. Abu-Yunis

Abstract

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

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.

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.

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.

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.

Glomb T, Swiatek P. Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives, Int. J. Mol. Sci., 2021; 22: 6979-7002.

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.

Kiran S. 1,3,4-oxadiazole a potent drug candidate with various pharmacological activities, Inter. J. Pharm. Pharm. Sc., 2021; 3(3): 9-16.

Siwach A, Verma PK. Therapeutic potential of oxadiazole or furadiazole containing compounds. BMC Chem., 2020;14(1): 70-79.

Hicks C, Gulick RM. Raltegravir: The First HIV Type 1 Integrase Inhibitor. Clin. Infect. Dise., 2009; 48(7): 931-939.

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.

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.

Aiswarya G, Divekar K. A Review on Synthesis of Various Oxadiazole Derivatives Applying Green Chemistry Methods Der Pharm. Lett., 2021; 13(7): 108-131.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Methods for dilution antimicrobial susceptibility tests for bacteria grow aerobically. Approved Standard M7-A4. Clinical and Laboratory Standards Institute, Wayne, Pa, USA, 2005.

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How to Cite
Dalloul, H. M., & Abu-Yunis, K. R. (2023). Synthesis and Biological Activities Evaluation of Novel Spiroheterocycles Containing 1,3,4-Oxadiazoline Moiety. European Journal of Advanced Chemistry Research, 4(2), 1–7. https://doi.org/10.24018/ejchem.2023.4.2.127