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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Review Article

A Bird's Eye Review of Recent Reports on 1,3,4-oxadiazoles' Anti-inflammatory Insights Perspectives

Author(s): Tarun Chaudhary* and Prabhat Kumar Upadhyay

Volume 21, Issue 5, 2024

Published on: 19 July, 2023

Page: [595 - 606] Pages: 12

DOI: 10.2174/1570179420666230508124847

Price: $65

Abstract

Anti-inflammatory agents suppress inflammatory mediators such as prostaglandins, prostacyclins, cytokines, thromboxane, histamine, bradykinins, COX-I and COX-II, 5-LOX, and other substances. These inflammatory chemicals create inflammatory responses when tissue is injured by trauma, bacteria, heat, toxins, or other factors. These inflammatory reactions may result in fluid flow from the blood vessels into the tissues, resulting in swelling. When the therapeutic importance of these clinically beneficial medications in treating inflammation was recognized, it spurred the invention of even more powerful and important molecules. Oxadiazole derivatives are exceptionally potent NSAIDs, and they are widely used. Comprehensive biochemical, structure-activity-relationship and pharmacological investigations have demonstrated that these 1,3,4-oxadiazole compounds exhibit anti-inflammatory properties. This review article outlines the synthesis scheme for 1,3,4-oxadiazole used in treating inflammation.

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[1]
Kar, A. Medicinal chemistry; New Age International, 2005.
[2]
Mahapatra, D.K.; Bharti, S.K. Handbook of Research on Medicinal Chemistry: Innovations and Methodologies; Apple Academic Press: New Jersey, 2017.
[http://dx.doi.org/10.1201/9781315207414]
[3]
Patrick, G.L. An Introduction to Medicinal Chemistry; Oxford University Press, 2013.
[4]
Alagarsamy, V. Textbook of Medicinal Chemistry; Elsevier Health Sciences, 2013.
[5]
Chhajed, S.S.; Upasani, C.D.; Wadher, S.J.; Mahapatra, D.K. Medicinal Chemistry; Career Publications Private Limited: Nashik, 2017.
[6]
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, 97(3), 572-591.
[http://dx.doi.org/10.1111/cbdd.13795] [PMID: 32946168]
[7]
Ajani, O.O.; Iyaye, K.T. Recent advances on oxadiazole motifs: Synthesis, reactions and biological activities. Mediterr. J. Chem., 2020, 10(5), 418.
[http://dx.doi.org/10.13171/mjc10502005121200ooa]
[8]
Mishra, A.K.; Kumar, A.; Sahu, J.K. Recent advancements in biological activities of oxadiazole and their derivatives: A review. Lett. Org. Chem., 2020, 17(6), 409-429.
[http://dx.doi.org/10.2174/1570178617666191220115426]
[9]
Aljamali, N.M.; Mahmood, R.M.; Atiya, R.N.; Wannas, F.A. Review on preparation methods & application fields of oxadiazole. Int. J. Chem. Synth. Chem. React., 2020, 6(1), 49-60.
[10]
Khalil, M.T.; Khan, S.G.; Li, B.; Wu, X.; Ali, U.; Shoaib, M. A critical review on synthesis and biological screening of 1, 3, 4-oxadiazole based NSAIDs derivatives. Life Sci. J., 2020, 17(10), 1-15.
[11]
Kaur, V.; Kaur, P.; Goswami, M. Pharmacological activities of oxadiazole derivatives: A review. Eur J Biomed., 2018, 5(5), 211-221.
[12]
Chaudhary, T.; Upadhyay, P.K. A review on novel synthesis approaches and biological activities of 1,2,4-oxadiazole and 1,3,4-Oxadiazole tailored compounds. Curr. Org. Synth., 2022, 19(6), 731-747.
[http://dx.doi.org/10.2174/1570179419666220216122238] [PMID: 35170412]
[13]
Birle, R.; Chaturvedi, P.; Dubey, A.; Engla, G.; Kushwah, N. A review on substituted 1, 3, 4-oxadiazole and its biological activities. Int. J. Res. Eng. Sci. Manag., 2020, 3(1), 86-92.
[14]
Bistrian, B. Systemic response to inflammation. Nutr. Rev., 2007, 65(12), 170-172.
[http://dx.doi.org/10.1301/nr.2007.dec.S170-S172] [PMID: 18240543]
[15]
Mahapatra, D.K.; Shivhare, R.S.; Kumar, P. Murrayanine-chalcone transformed into novel pyrimidine compounds demonstrated promising anti-inflammatory activity. Asian J. Pharmaceut. Res., 2018, 8(1), 6-10.
[http://dx.doi.org/10.5958/2231-5691.2018.00002.3]
[16]
Kuprash, D.V.; Nedospasov, S.A. Molecular and cellular mechanisms of inflammation. Biochemistry, 2016, 81(11), 1237-1239.
[http://dx.doi.org/10.1134/S0006297916110018] [PMID: 27914449]
[17]
Larsen, G.L.; Henson, P.M. Mediators of inflammation. Annu. Rev. Immunol., 1983, 1(1), 335-359.
[http://dx.doi.org/10.1146/annurev.iy.01.040183.002003] [PMID: 6399978]
[18]
Ciaccia, L. Fundamentals of inflammation. Yale J. Biol. Med., 2011, 84(1), 64.
[19]
Trowbridge, H.O.; Emling, R.C.; Fornatora, M. Inflammation. A review of the process. Implant Dent., 1997, 6(3), 238.
[http://dx.doi.org/10.1097/00008505-199700630-00025]
[20]
Mahapatra, D.K.; Bharti, S.K.; Asati, V. Chalcone derivatives: Anti-inflammatory potential and molecular targets perspectives. Curr. Top. Med. Chem., 2017, 17(28), 3146-3169.
[http://dx.doi.org/10.2174/1568026617666170914160446] [PMID: 28914193]
[21]
Kulinsky, V.I. Biochemical aspects of inflammation. Biochemistry, 2007, 72(6), 595-607.
[http://dx.doi.org/10.1134/S0006297907060028] [PMID: 17630904]
[22]
Libby, P. Inflammatory mechanisms: The molecular basis of inflammation and disease. Nutr. Rev., 2007, 65(12), 140-146.
[http://dx.doi.org/10.1301/nr.2007.dec.S140-S146] [PMID: 18240538]
[23]
Abdulkhaleq, L.A.; Assi, M.A.; Abdullah, R.; Zamri-Saad, M.; Taufiq-Yap, Y.H.; Hezmee, M.N.M. The crucial roles of inflammatory mediators in inflammation: A review. Vet. World, 2018, 11(5), 627-635.
[http://dx.doi.org/10.14202/vetworld.2018.627-635] [PMID: 29915501]
[24]
Ahmed, A.U. An overview of inflammation: Mechanism and consequences. Front. Biol., 2011, 6(4), 274-281.
[http://dx.doi.org/10.1007/s11515-011-1123-9]
[25]
Germolec, D.R.; Shipkowski, K.A.; Frawley, R.P.; Evans, E. Markers of inflammation; Immunotoxicity Testing, 2018, pp. 57-79.
[26]
Ashley, N.T.; Weil, Z.M.; Nelson, R.J. Inflammation: Mechanisms, costs, and natural variation. Annu. Rev. Ecol. Evol. Syst., 2012, 43(1), 385-406.
[http://dx.doi.org/10.1146/annurev-ecolsys-040212-092530]
[27]
Buckley, C.D.; Gilroy, D.W.; Serhan, C.N.; Stockinger, B.; Tak, P.P. The resolution of inflammation. Nat. Rev. Immunol., 2013, 13(1), 59-66.
[http://dx.doi.org/10.1038/nri3362] [PMID: 23197111]
[28]
Schmid-Schönbein, G.W. Analysis of inflammation. Annu. Rev. Biomed. Eng., 2006, 8(1), 93-151.
[http://dx.doi.org/10.1146/annurev.bioeng.8.061505.095708] [PMID: 16834553]
[29]
Krishnamoorthy, S.; Honn, K.V. Inflammation and disease progression. Cancer Metastasis Rev., 2006, 25(3), 481-491.
[http://dx.doi.org/10.1007/s10555-006-9016-0] [PMID: 17103050]
[30]
Lawrence, T.; Gilroy, D.W. Chronic inflammation: A failure of resolution? Int. J. Exp. Pathol., 2007, 88(2), 85-94.
[http://dx.doi.org/10.1111/j.1365-2613.2006.00507.x] [PMID: 17408451]
[31]
Rankin, J.A. Biological mediators of acute inflammation. AACN Clin. Issues, 2004, 15(1), 3-17.
[http://dx.doi.org/10.1097/00044067-200401000-00002] [PMID: 14767362]
[32]
Shukla, C.; Srivastava, S. Biologically active oxadiazole. J. Drug Deliv. Ther., 2015, 5(6), 8-13.
[http://dx.doi.org/10.22270/jddt.v5i6.1100]
[33]
Gilani, S.J.; Zzaman, M.T.; Nagarajan, K.; Goel, R.; Arora, A. Progress in the pharmacological potential of oxadiazoles: a review. Int Bull Drug Res., 2019, 2(1), 132-146.
[34]
Anjali Jha; Sen, A.; Malla, R.R. Chemistry of oxadiazole analogues: Current status and applications. Russ. J. Bioorganic Chem., 2021, 47(3), 670-680.
[http://dx.doi.org/10.1134/S1068162021030092]
[35]
Patil, S.M. A review on oxadiazole derivatives and their biological activities. Int J Pharm Res., 2021, 13(2), 2901-2905.
[36]
Mancini, R.S.; Barden, C.J.; Weaver, D.F.; Reed, M.A. Furazans in medicinal chemistry. J. Med. Chem., 2021, 64(4), 1786-1815.
[http://dx.doi.org/10.1021/acs.jmedchem.0c01901] [PMID: 33569941]
[37]
Rana, K.; Salahuddin; Sahu, J.K. Significance of 1,3,4-Oxadiazole containing compounds in new drug development. Curr. Drug Res. Rev., 2021, 13(2), 90-100.
[http://dx.doi.org/10.2174/2589977512666201221162627] [PMID: 33349230]
[38]
Asif, M. A mini review on pharmacological activities of oxadiazole and thiadiazole compounds. Moroccan J Chem., 2014, 2(2), 2-14.
[39]
Bhasin, G.; Srivastava, R.; Singh, R. Oxadiazoles: Moiety to synthesis and utilize. J Iranian Chem Soc., 2021, 7, 1-3.
[40]
Bala, S.; Saini, V.; Kamboj, S.; Prasad, D.N. Review exploring antiinflammatory potential of 1, 3, 4-oxadiazole derivatives as promising lead. Int. J. Pharm. Sci. Rev. Res., 2012, 17(2), 84-89.
[41]
Sun, J.; Makawana, J.; Zhu, H.L. 1, 3, 4-oxadiazole derivatives as potential biological agents. Mini Rev. Med. Chem., 2013, 13(12), 1725-1743.
[http://dx.doi.org/10.2174/13895575113139990071] [PMID: 23815585]
[42]
Salahuddin, M.A.; Mazumder, A.; Yar, M.S.; Mazumder, R.; Chakraborthy, G.S.; Ahsan, M.J.; Rahman, M.U. Updates on synthesis and biological activities of 1,3,4-oxadiazole: A review. Synth. Commun., 2017, 47(20), 1805-1847.
[http://dx.doi.org/10.1080/00397911.2017.1360911]
[43]
Ruan, B.F.; Guo, Q.L.; Li, Q.S.; Li, L.Z.; Deora, G.S.; Zhou, B.G. A review of the biological activities of heterocyclic compounds comprising oxadiazole moieties. Curr. Top. Med. Chem., 2022, 22(7), 578-599.
[http://dx.doi.org/10.2174/1568026622666220202123651] [PMID: 35114924]
[44]
Saha, R.; Tanwar, O.; Marella, A.; Mumtaz Alam, M.; Akhter, M. Recent updates on biological activities of oxadiazoles. Mini Rev. Med. Chem., 2013, 13(7), 1027-1046.
[http://dx.doi.org/10.2174/1389557511313070007] [PMID: 22512577]
[45]
Verma, G.; Khan, M.F.; Akhtar, W.; Alam, M.M.; Akhter, M.; Shaquiquzzaman, M. A review exploring therapeutic worth of 1, 3, 4-oxadiazole tailored compounds. Mini Rev. Med. Chem., 2019, 19(6), 477-509.
[http://dx.doi.org/10.2174/1389557518666181015152433] [PMID: 30324877]
[46]
Chawla, G.; Naaz, B.; Siddiqui, A.A. Exploring 1, 3, 4-oxadiazole scaffold for anti-inflammatory and analgesic activities: A review of literature from 2005-2016. Mini Rev. Med. Chem., 2018, 18(3), 216-233.
[PMID: 28137242]
[47]
Bala, S.; Kamboj, S.; Kumar, A. Heterocyclic 1, 3, 4-oxadiazole compounds with diverse biological activities: A comprehensive review. J. Pharm. Res., 2010, 3(12), 2993-2997.
[48]
Yadav, S.; Vashist, N.; Gahlot, V.; Rajput, A.; Maratha, S. Oxadiazole and their synthetic analogues: An updated review. Int. J. Pharm. Biol. Arch., 2018, 9(3), 4-9.
[49]
Zachariah, S.M.; Mridula, R.; Namy, G.; Ashif, M.S. A review on oxadiazole. Res. J. Pharm. Biol. Chem. Sci., 2015, 6(2), 205-219.
[50]
Siwach, A.; Verma, P.K. Therapeutic potential of oxadiazole or furadiazole containing compounds. BMC Chem., 2020, 14(1), 70.
[http://dx.doi.org/10.1186/s13065-020-00721-2] [PMID: 33372629]
[51]
Kumar, K.A.; Jayaroopa, P.; Kumar, G.V. Comprehensive review on the chemistry of 1, 3, 4-oxadiazoles and their applications. Int. J. Chem. Technol. Res., 2012, 4(4), 1782-1791.
[52]
Chawla, G. 1, 2, 4-Oxadiazole as a privileged scaffold for anti-inflammatory and analgesic activities: A review. Mini Rev. Med. Chem., 2018, 18(18), 1536-1547.
[http://dx.doi.org/10.2174/1389557518666180524112050] [PMID: 29792145]
[53]
Somani, R.R.; Shirodkar, P.Y. Oxadiazole: A biologically important heterocycle. ChemInform, 2009, 1(1), 130-140.
[54]
Patel, K.D.; Prajapati, S.M.; Panchal, S.N.; Patel, H.D. Review of synthesis of 1, 3, 4-oxadiazole derivatives. Synth. Commun., 2014, 44(13), 1859-1875.
[http://dx.doi.org/10.1080/00397911.2013.879901]
[55]
Khalilullah, H.; Ahsan, M.; Hedaitullah, M.; Khan, S.; Ahmed, B. 1, 3, 4-oxadiazole: a biologically active scaffold. Mini Rev. Med. Chem., 2012, 12(8), 789-801.
[http://dx.doi.org/10.2174/138955712801264800] [PMID: 22512560]
[56]
Vaidya, A.; Jain, S.; Jain, P.; Jain, P.; Tiwari, N.; Jain, R.; Jain, R.; Jain, A.K.; Agrawal, R.K. Synthesis and biological activities of oxadiazole derivatives: A review. Mini Rev. Med. Chem., 2016, 16(10), 825-845.
[http://dx.doi.org/10.2174/1389557516666160211120835] [PMID: 26864552]
[57]
Kashid, B.B.; Salunkhe, P.H.; Dongare, B.B.; More, K.R.; Khedkar, V.M.; Ghanwat, A.A. Synthesis of novel of 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives and their in vitro anti-inflammatory, anti-oxidant evaluation, and molecular docking study. Bioorg. Med. Chem. Lett., 2020, 30(12), 127136.
[http://dx.doi.org/10.1016/j.bmcl.2020.127136] [PMID: 32280025]
[58]
Szczukowski, Ł.; Krzyżak, E.; Zborowska, A.; Zając, P.; Potyrak, K.; Peregrym, K.; Wiatrak, B.; Marciniak, A.; Świątek, P. Design, synthesis and comprehensive investigations of pyrrolo[3,4-d]pyridazinone-Based 1,3,4-oxadiazole as new class of selective COX-2 inhibitors. Int. J. Mol. Sci., 2020, 21(24), 9623.
[http://dx.doi.org/10.3390/ijms21249623] [PMID: 33348757]
[59]
Kumar, D.; Kumar, R.R.; Pathania, S.; Singh, P.K.; Kalra, S.; Kumar, B. Investigation of indole functionalized pyrazoles and oxadiazoles as anti-inflammatory agents: Synthesis, in-vivo, in-vitro and in-silico analysis. Bioorg. Chem., 2021, 114, 105068.
[http://dx.doi.org/10.1016/j.bioorg.2021.105068] [PMID: 34130110]
[60]
Nesaragi, A.R.; Kamble, R.R.; Dixit, S.; Kodasi, B.; Hoolageri, S.R.; Bayannavar, P.K.; Dasappa, J.P.; Vootla, S.; Joshi, S.D.; Kumbar, V.M. Green synthesis of therapeutically active 1,3,4-oxadiazoles as antioxidants, selective COX-2 inhibitors and their in silico studies. Bioorg. Med. Chem. Lett., 2021, 43, 128112.
[http://dx.doi.org/10.1016/j.bmcl.2021.128112]
[61]
El-Sayed, N.A.; Nour, M.S.; Salem, M.A.; Arafa, R.K. New oxadiazoles with selective-COX-2 and EGFR dual inhibitory activity: Design, synthesis, cytotoxicity evaluation and in silico studies. Eur. J. Med. Chem., 2019, 183, 111693.
[http://dx.doi.org/10.1016/j.ejmech.2019.111693] [PMID: 31539778]

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