Advance in the Synthesis of Oxadiazole Based Heterocyclic Compound
Abstract
The five members of the heterocyclic ring 1,3,4-oxadiazole are necessary for the production of strong bioactive molecules. Numerous pharmacological effects, including anti-inflammatory, antibacterial, anticancer, antitubercular, anticonvulsant, anti-HIV, hypoglycemic, and antioxidant qualities, are exhibited by this intriguing class of chemicals. We have created four novel 1,3,4-oxadiazole compounds in the continuing study, which are sourced from the NSAID Ibuprofen. Melting point analysis and TLC were used to verify the compounds' purity. Open capillary methods were used to ascertain the melting point, and it was left unaltered. The structure of the four freshly synthesized compounds was confirmed using FTIR and 1HNMR spectroscopy. The creation of procedures for the environmentally friendly synthesis of materials and chemicals is referred to as &outgreen synthetic protocol. Various methods that are both energy-efficient and environmentally friendly, including microwave irradiation, ultrasound-assisted synthesis, photo-catalysis employing ultraviolet, visible, and infrared light, molecular sieving, grinding, milling techniques, and others, are employed in the creation of diverse biologically active substances. These procedures are regarded as sustainable technology and have gained value as green protocols for the synthesis of novel medicinal compounds because they have several advantages over traditional synthetic techniques. This idea is the basis for the synthesis of oxadiazole derivatives using a microwave irradiation approach, which decreases the generation of byproduct and increases the product yield quantitatively in a shorter reaction time. Because of this, the synthesis of pharmacological molecules under microwave irradiation adheres to a green chemistry strategy, which uses a set of guidelines to reduce or eliminate the use of dangerous and toxic ingredients in the design, production, and use of chemicals. By using cleaner solvents, catalysts, and appropriate reaction conditions, this strategy helps to reduce environmental pollution and boosts energy efficiency and atom economy.
References
Xuan, T.D.; Elzaawely, A.A.; Fukuta, M.; Tawata, S. Herbicidal and fungicidal activities of lactones in Kava (Piper methysticum). J. Agric. Food Chem. 2006, 54, 720–725.
Yajima, W.; Rahman, M.H.; Das, D.; Suresh, M.R.; Kav, N.N.V. Detection of Sclerotinia sclerotiorum Using a Monomeric and Dimeric Single-Chain Fragment Variable (scFv) Antibody. J. Agric. Food Chem. 2008, 56, 9455–9463.
Fisher, M.C.; Henk, D.; Briggs, C.J.; Brownstein, J.S.; Madoff, L.C.; McCraw, S.L.; Gurr, S.J. Emerging fungal threats to animal, plant and ecosystem health. Nature 2012, 484, 186–194
Mickevičius V, Vaickelioniene R, Sapijanskaite B. Synthesis of substituted 1,3,4-oxadiazole derivatives. Chemistry of Heterocyclic Compounds. 2009;45(2):215–218.
Ramazani A, Souldozi A. Iminophosphorane-mediated one-pot synthesis of 1,3,4-oxadiazole derivatives. Arkivoc. 2008;2008(16):235–242.
Fungal Disease Frequency. Available online: https://gaffi.org/why/fungal-disease-frequency/ (accessed on 4 April 2022).
Wu, Y.Y.; Shao, W.B.; Zhu, J.J.; Long, Z.Q.; Liu, L.W.; Wang, P.Y.; Li, Z.; Yang, S. Novel 1,3,4-Oxadiazole-2-carbohydrazides as Prospective Agricultural Antifungal Agents Potentially Targeting Succinate Dehydrogenase. J. Agric. Food Chem. 2019, 67, 13892–13903.
Akhter, M.; Husain, A.; Azad, B.; Ajmal, M. Aroylpropionic acid based 2,5-disubstituted-1,3,4-oxadiazoles: Synthesis and their anti-inflammatory and analgesic activities. Eur. J. Med. Chem. 2009, 44, 2372–2378.
Glomb, T.; Świątek, P. Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives. Int. J. Mol. Sci. 2021, 22, 6979.
Wróblowska, M.; Kudelko, A.; Kuźnik, N.; Łaba, K.; Łapkowski, M. Synthesis of Extended 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Derivatives in the Suzuki Cross-coupling Reactions. J. Heterocycl. Chem. 2017, 54, 1550–1557.
Ajay Kumar, K.; Jayaroopa, P.; Vasanth Kumar, G. Comprehensive review on the chemistry of 1,3,4-oxadiazoles and their applications. Int. J. ChemTech Res. 2012, 4, 1782–1791.
Siwach, A.; Verma, P.K. Therapeutic potential of oxadiazole or furadiazole containing compounds. BMC Chem. 2020, 14, 70.
M. Farah, A. Pilotti. Drug Discovery Today, 2006, 11(3-4), 165-174.
Verma G, Chashoo G, Ali A, Khan MF, Akhtar W, Ali I, Akhtar M, Alam MM, Shaquiquzzaman M (2018) Synthesis of pyrazole acrylic acid based oxadiazole and amide derivatives as antimalarial and anticancer agents. Bioorg Chem 77:106–124
Tantray MA, Khan I, Hamid H, Alam MS, Dhulap A, Kalam A (2018) Synthesis of benzimidazole-linked-1,3,4-oxadiazole carboxamides as GSK-inhibitors with in vivo antidepressant activity. Bioorg Chem 77:393–401
Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kapple KD (2002) Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 45:2615–2623
Ertl P, Rohde B, Selzer P (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43:3714–3717
Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kapple KD (2002) Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 45:2615–2623
Blower TR, Williamson BH, Kerns RJ, Berger JM (2016) Crystal structure and stability of gyrase fluoroquinolone cleaved complexes from Mycobacterium tuberculosis. Proc Natl Acad Sci USA 113:1706–1713
Mahadevi AS, Sastry GN (2013) Cation-p interaction: its role and relevevance in chemistry, biology, and material science. Chem Rev 113:2100–2138
Refbacks
- There are currently no refbacks.


