Coumarin-Oxadiazole Derivatives: Synthesis and Pharmacological Properties

Author(s): Nurhayatun S. Abdul Razak, Joazaizulfazli Jamalis*, Subhash Chander, Roswanira Abdul Wahab, Deepak P. Bhagwat, Terry K. Smith, Murugesan Sankaranarayanan

Journal Name: Mini-Reviews in Organic Chemistry

Volume 17 , Issue 7 , 2020


Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


Abstract:

Coumarin and oxadiazole moieties ubiquitously occur in a wide range of natural products and are valued for their varied and beneficial pharmacological activities. Herein, this review focuses on various documented techniques used by researchers to synthesize an assortment of biologically active coumarin-oxadiazole scaffolds. Also, the common techniques discussed are used to establish the wide-range of biological activities of the synthesized coumarin and oxadiozole derivatives, including; antioxidant, anthelmintic, antimicrobial, anti-tuberculosis, analgesic, anti-inflammatory, cytotoxicity and anticonvulsant. Additionally, the current, well-established drugs synthesized using coumarin-oxadiazole scaffolds are typically dispensed in regular clinical practice are also highlighted in this review paper.

Keywords: Biological activities, coumarin-oxadiazole, coumarins, drugs, oxadiazoles, synthesis.

[1]
Shneine, J.K.; Alaraji, Y.H. Chemistry of 1,2,4-triazole: A review article. Int. J. Sci. Res. (Ahmedabad), 2016, 5(3), 1411-1423.
[2]
de Oliveira, C.S.; Lira, B.F.; Barbosa-Filho, J.M.; Lorenzo, J.G.F.; de Athayde-Filho, P.F. Synthetic approaches and pharmacological activity of 1,3,4-oxadiazoles: A review of the literature from 2000-2012. Molecules, 2012, 17(9), 10192-10231.
[http://dx.doi.org/10.3390/molecules170910192] [PMID: 22926303]
[3]
Desai, N.C.; Amit, M.D. Conventional and microwave techniques for synthesis and antimicrobial studies of novel 1-[2-(2-chloro(3-quinolyl))-5-(4-nitrophenyl)-(1,3,4-oxadiazolin-3-yl)]-3-(aryl)-prop-2-en-1-ones. Med. Chem. Res., 2011, 21(7), 1480-1490.
[http://dx.doi.org/10.1007/s00044-011-9670-9]
[4]
Bakht, M.A.; Yar, M.S.; Abdel-Hamid, S.G.; Al Qasoumi, S.I.; Samad, A. Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives. Eur. J. Med. Chem., 2010, 45(12), 5862-5869.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.069] [PMID: 20965619]
[5]
Jha, K.K.; Samad, A.; Kumar, Y.; Shaharyar, M.; Khosa, R.L.; Jain, J.; Kumar, V.; Singh, P. Design, synthesis and biological evaluation of 1,3,4-oxadiazole derivatives. Eur. J. Med. Chem., 2010, 45(11), 4963-4967.
[http://dx.doi.org/10.1016/j.ejmech.2010.08.003] [PMID: 20817328]
[6]
Chawla, R.; Arora, A.; Parameswaran, M.K.; Chan, P.; Sharma, D.; Michael, S.; Ravi, T.K. Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents. Acta Pol. Pharm., 2010, 67(3), 247-253.
[PMID: 20524426]
[7]
Yu, W.; Huang, G.; Zhang, Y.; Liu, H.; Dong, L.; Yu, X.; Li, Y.; Chang, J. I2-mediated oxidative C-O bond formation for the synthesis of 1,3,4-oxadiazoles from aldehydes and hydrazides. J. Org. Chem., 2013, 78(20), 10337-10343.
[http://dx.doi.org/10.1021/jo401751h] [PMID: 24059837]
[8]
Kharche, A.A.; Bairagi, S.H.; Gorde, N.K.; Laddha, S.S. 1,3,4-oxadiazole: A new profile of biological activities. Asian J. Res. Chem, 2011, 4(1), 1-12.
[9]
Ananthan, S.; Faaleolea, E.R.; Goldman, R.C.; Hobrath, J.V.; Kwong, C.D.; Laughon, B.E.; Maddry, J.A.; Mehta, A.; Rasmussen, L.; Reynolds, R.C.; Secrist, J.A., III; Shindo, N.; Showe, D.N.; Sosa, M.I.; Suling, W.J.; White, E.L. High-throughput screening for inhibitors of Mycobacterium tuberculosis H37Rv. Tuberculosis (Edinb.), 2009, 89(5), 334-353.
[http://dx.doi.org/10.1016/j.tube.2009.05.008] [PMID: 19758845]
[10]
Grover, J.; Jachak, S.M. Coumarins as privileged scaffold for anti-inflammatory drug development. RSC Adv., 2015, 5(4), 38892-38905.
[http://dx.doi.org/10.1039/C5RA05643H]
[11]
Fylaktakidou, K.C.; Hadjipavlou-Litina, D.J.; Litinas, K.E.; Nicolaides, D.N. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities. Curr. Pharm. Des., 2004, 10(30), 3813-3833.
[http://dx.doi.org/10.2174/1381612043382710] [PMID: 15579073]
[12]
Hadjipavlou-Litina, D.J.; Litinas, K.E.; Kontogiorgis, C. The anti-inflammatory effect of coumarin and its derivatives. Antiinflamm. Antiallergy Agents Med. Chem., 2007, 6(4), 293-306.
[http://dx.doi.org/10.2174/187152307783219989]
[13]
Taniyama, H.; Tanaka, Y.; Uchida, H. Chemotherapeutics for Mycobacterium tuberculosis, II, synthesis of some 2-thiazolyl hydrazones and their antibacterial activity on Mycobacterium tuberculosis. J Pharm Soc Japan, 1954, 74(11), 370-373.
[http://dx.doi.org/10.1248/yakushi1947.74.4_370]
[14]
Cardoso, S.H.; Barreto, M.B.; Lourenço, M.C.S.; Henriques, Md.; Candéa, A.L.; Kaiser, C.R.; de Souza, M.V.; Souza, M.V.N.D. Antitubercular activity of new coumarins. Chem. Biol. Drug Des., 2011, 77(6), 489-493.
[http://dx.doi.org/10.1111/j.1747-0285.2011.01120.x] [PMID: 21414146]
[15]
Huang, L.; Yuan, X.; Yu, D.; Lee, K.H.; Chen, C.H. Mechanism of action and resistant profile of anti-HIV-1 coumarin derivatives. Virology, 2005, 332(2), 623-628.
[http://dx.doi.org/10.1016/j.virol.2004.11.033] [PMID: 15680427]
[16]
Emami, S.; Dadashpour, S. Current developments of coumarin-based anti-cancer agents in medicinal chemistry. Eur. J. Med. Chem., 2015, 102(8), 611-630.
[http://dx.doi.org/10.1016/j.ejmech.2015.08.033] [PMID: 26318068]
[17]
Sudha, B.N.; Sridhar, C.; Sastry, V.G.; Reddy, Y.S.R.; Sreevidya, O.; Lavanya, V.; Jyothi, V.A.; Nagesh, V.; Sen, S.; Chakraborty, R. Synthesis, characterization and anthelmintic activity of 3-(4-acetyl-5-phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one derivatives. Indian J. Chem., 2013, 52B(3), 422-427.
[http://dx.doi.org/10.1002/chin.201327126]
[18]
Yamgar, R.S.; Sawant, S.S. Review: An update on drugs discovery and natural products. Asian J. Pharm. Sci. Tech., 2015, 5(3), 137-155.
[19]
Maftei, C.V.; Fodor, E.; Jones, P.G.; Daniliuc, C.G.; Franz, M.H.; Kelter, G.; Fiebig, H.H.; Tamm, M.; Neda, I. Novel bioactive 1,2,4-oxadiazole natural product analogs. Synthesis, structural analysis and potential antitumor activity. Rev. Roum. Chim., 2015, 60(1), 75-83.
[20]
Carbone, M.; Li, Y.; Irace, C.; Mollo, E.; Castelluccio, F.; Di Pascale, A.; Cimino, G.; Santamaria, R.; Guo, Y.W.; Gavagnin, M. Structure and cytotoxicity of phidianidines A and B: First finding of 1,2,4-oxadiazole system in a marine natural product. Org. Lett., 2011, 13(10), 2516-2519.
[http://dx.doi.org/10.1021/ol200234r] [PMID: 21506595]
[21]
Yokoi, I.; Takeuchi, H.; Sakai, A.; Mori, A. Effects of ibotenic acid, quisqualic acid and their relatives on the excitability of an identifiable giant neurone of an African giant snail (Achatina fulica Férussac). Experientia, 1977, 33(3), 363-366.
[http://dx.doi.org/10.1007/BF02002829] [PMID: 858370]
[22]
Venugopala, K.N.; Rashmi, V.; Odhav, B. Review on natural coumarin lead compounds for their pharmacological activity. BioMed Res. Int., 2013, 2013(2)963248
[http://dx.doi.org/10.1155/2013/963248] [PMID: 23586066]
[23]
Kim, H.J.; Jang, S.I.; Kim, Y.J.; Chung, H.T.; Yun, Y.G.; Kang, T.H.; Jeong, O.S.; Kim, Y.C. Scopoletin suppresses pro-inflamm-atory cytokines and PGE2 from LPS-stimulated cell line, RAW 264.7 cells. Fitoterapia, 2004, 75(3-4), 261-266.
[http://dx.doi.org/10.1016/j.fitote.2003.12.021] [PMID: 15158982]
[24]
Chang, T.N.; Deng, J.S.; Chang, Y.C.; Lee, C.Y.; Jung-Chun, L.; Lee, M.M.; Peng, W.H.; Huang, S.S.; Huang, G.J. Ameliorative effects of scopoletin from Crossostephium chinensis against inflammation pain and its mechanisms in mice. Evid. Based Complement. Alternat. Med., 2012, 2012(7)595603
[PMID: 22991572]
[25]
Leal, L.K.A.M.; Matos, M.E.; Matos, F.J.; Ribeiro, R.A.; Ferreira, F.V.; Viana, G.S. Antinociceptive and antiedematogenic effects of the hydroalcoholic extract and coumarin from Torresea cearensis Fr. All. Phytomedicine, 1997, 4(3), 221-227.
[http://dx.doi.org/10.1016/S0944-7113(97)80071-2] [PMID: 23195479]
[26]
Sunthitikawinsakul, A.; Kongkathip, N.; Kongkathip, B.; Phonnakhu, S.; Daly, J.W.; Spande, T.F.; Nimit, Y.; Rochanaruangrai, S.; Rochanaruangrai, S. Coumarins and carbazoles from Clausena excavata exhibited antimycobacterial and antifungal activities. Planta Med., 2003, 69(2), 155-157.
[http://dx.doi.org/10.1055/s-2003-37716] [PMID: 12624822]
[27]
Bell, R.G.; Caldwell, P.T. Mechanism of warfarin resistance. Warfarin and the metabolism of vitamin K 1. Biochemistry, 1973, 12(9), 1759-1762.
[http://dx.doi.org/10.1021/bi00733a015] [PMID: 4699235]
[28]
Lino, C.S.; Taveira, M.L.; Viana, G.S.B.; Matos, F.J.A. Analgesic and anti-inflammatory activities of Justiciapectoralis Jacq and its main constituents: Coumarin and umbelliferone. Phytother. Res., 1997, 11(10), 211-215.
[http://dx.doi.org/10.1002/(SICI)1099-1573(199705)11:3<211:AID-PTR72>3.0.CO;2-W]
[29]
Amir, M.; Agarwal, R. Synthesis and antiinflammatory activity of 5-(8-quinolinoxy methyl)-1,3,4-oxadiazole/1,3,4-thiadiazole and 1,2,4 (H) triazole. Indian J. Chem., 1998, 7(3), 225-228.
[30]
Kumar, A.; Mirdula, T.; Srivastava, V.K. Newer potential quinazolinones as hypotensive agents. Indian J. Chem., 2003, 42B(9), 2142-2145.
[31]
Mahesh, M.; Bheemaraju, G.; Manjunath, G.; Venkata Ramana, P. Synthesis of new oxadiazole, pyrazole and pyrazolin-5-one bearing 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide analogs as potential antibacterial and antifungal agents. Ann. Pharm. Fr., 2016, 74(1), 34-44.
[http://dx.doi.org/10.1016/j.pharma.2015.07.002] [PMID: 26316428]
[32]
Zhang, L.; Xia, Y.; Li, M.; Li, D.; Hou, R. Synthesis, photophysical and electrochemical properties of symmetric silicon-linked coumarin-oxadiazole derivatives. Tetrahedron, 2016, 72(9), 7438-7442.
[http://dx.doi.org/10.1016/j.tet.2016.09.033]
[33]
Elbastawesy, M.A.I.; Youssif, B.G.M.; Abdelrahman, M.H.; Hayallah, A.M. Synthesis and biological evaluation of some new coumarin derivatives as potential antimicrobial, analgesic and anti-inflammatory agents. Pharma Chem., 2015, 7(10), 337-349.
[34]
Khan, M. Synthesis and pharmacological evaluation of novel coumarin derivatives. Int. J. Pharm. Innov., 2012, 2(6), 12-19.
[35]
Charistos, D.A.; Vagenas, G.V.; Tzavellas, L.C.; Tsoleridis, C.A.; Rodios, N.A. Synthesis and a UV and IR spectral study of some 2-aryl-D-2-1,3,4-oxadiazoline-5-thiones. J. Heterocycl. Chem., 2009, 31(6), 1593-1598.
[http://dx.doi.org/10.1002/jhet.5570310653]
[36]
Morsy, S.A.; Farahat, A.A.; Nasr, M.N.A.; Tantawy, A.S. Synthesis, molecular modeling and anticancer activity of new coumarin containing compounds. Saudi Pharm. J., 2017, 25(6), 873-883.
[http://dx.doi.org/10.1016/j.jsps.2017.02.003] [PMID: 28951673]
[37]
Ibrar, A.; Tehseen, Y.; Khan, I.; Hameed, A.; Saeed, A.; Furtmann, N.; Bajorath, J.; Iqbal, J. Coumarin-thiazole and -oxadiazole derivatives: Synthesis, bioactivity and docking studies for aldose/aldehyde reductase inhibitors. Bioorg. Chem., 2016, 68(8), 177-186.
[http://dx.doi.org/10.1016/j.bioorg.2016.08.005] [PMID: 27544072]
[38]
Pattan, S.R.; Rabara, P.A.; Pattan, J.S.; Bukitagar, A.A.; Wakale, V.S.; Musmade, D.S. Synthesis and evaluation of some novel substituted 1,3,4-oxadiazole and pyrazole derivatives for antitubercular activity. Indian J. Chem., 2009, 48(10), 1453-1456.
[39]
Aydogan, F.; Turgut, Z.; Ocal, N.; Erdem, S.S. Synthesis and electronic structure of new aryl- and alkyl-substituted 1,3,4-oxadiazole-2-thione derivatives. Turk. J. Chem., 2002, 26(2), 159-169.
[40]
Patel, R.V.; Kumari, P.; Rajani, D.P.; Chikhalia, K.H. Synthesis of coumarin-based 1,3,4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides as antimicrobial and antituberculosis agents. Med. Chem. Res., 2013, 22(3), 195-210.
[http://dx.doi.org/10.1007/s00044-012-0026-x]
[41]
Bhat, M.A.; Siddiqui, N.; Khan, S.A. Synthesis of novel 3-(4-acetyl-5H/methyl-5-substituted phenyl-4,5-dihydro-1,3,4 oxadiazol-2-yl)-2H-chromen-2-ones as potential anticonvulsant agents. Acta Pol. Pharm., 2008, 65(2), 235-239.
[PMID: 18666431]
[42]
Patel, A.C.; Mahajan, D.H.; Chikhalia, K.H. Synthesis and antibacterial studies of some novel 2-(coumarin-3-yl)-5-mercapto-1,3,4-oxadiazoles containing 2,4,6-trisubstituted s-triazine derivatives. Phosphorus Sulfur Silicon Relat. Elem., 2010, 185(2), 368-376.
[http://dx.doi.org/10.1080/10426500902797285]
[43]
Khan, M.S.Y.; Akhtar, M. Synthesis of some new 2,5-disubstituted 1,3,4-oxadiazole derivatives and their biological activity. Indian J. Chem., 2003, 42B(4), 900-904.
[http://dx.doi.org/10.1002/chin.200332096]
[44]
Manojkumar, P.; Ravi, T.K.; Subbuchettiar, G. Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells. Acta Pharm., 2009, 59(2), 159-170.
[http://dx.doi.org/10.2478/v10007-009-0018-7] [PMID: 19564141]
[45]
Cacić, M.; Molnar, M.; Sarkanj, B.; Has-Schön, E.; Rajković, V. Synthesis and antioxidant activity of some new coumarinyl-1,3-thiazolidine-4-ones. Molecules, 2010, 15(10), 6795-6809.
[http://dx.doi.org/10.3390/molecules15106795] [PMID: 20881932]
[46]
Bhandari, S.V.; Bothara, K.G.; Raut, M.K.; Patil, A.A.; Sarkate, A.P.; Mokale, V.J. Design, synthesis and evaluation of antiinflammatory, analgesic and ulcerogenicity studies of novel S-substituted phenacyl-1,3,4-oxadiazole-2-thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives. Bioorg. Med. Chem., 2008, 16(4), 1822-1831.
[http://dx.doi.org/10.1016/j.bmc.2007.11.014] [PMID: 18248993]
[47]
Bobade, V.D.; Patil, S.V.; Gaikwad, N.D. Synthesis and biological evaluation of new thiosubstituted oxadiazole derivatives of coumarin under solvent-free conditions. J. Chem. Res., 2012, 36(1), 25-28.
[http://dx.doi.org/10.3184/174751912X13256103292351]
[48]
Hassan, G.S.; Farag, N.A.; Hegazy, G.H.; Arafa, R.K. Design and synthesis of novel benzopyran-2-one derivatives of expected antimicrobial activity through DNA Gyrase-B inhibition. Arch. Pharm. (Weinheim), 2008, 341(11), 725-733.
[http://dx.doi.org/10.1002/ardp.200700266] [PMID: 18973170]
[49]
El-masry, A.H.; Fahmy, H.H.; Abdelwahed, S.H.A. Synthesis and antimicrobial activity of some new benzimidazole derivatives. Molecules, 2000, 5(12), 1429-1438.
[http://dx.doi.org/10.3390/51201429]
[50]
Yar, M.S.; Siddiqui, A.A.; Ali, M.A. Synthesis and anti tuberculostatic activity of novel 1,3,4-oxadiazole derivatives. J. Chin. Chem. Soc. (Taipei), 2007, 54(1), 5-8.
[http://dx.doi.org/10.1002/jccs.200700002]
[51]
Ilango, K.; Biju, C.R. In-silico docking investigation, synthesis and cytotoxic studies of coumarin substituted 1, 3, 4-oxadiazole derivatives. J. Pahrm. Res., 2012, 5(3), 1514-1517.
[52]
Gong, X.R.; Xi, G.L.; Liu, Z.Q. Activity of coumarin-oxadiazole-appended phenol in habiting DNA oxidation and scavenging radical. Tet Lett., 2015, 56(45), 6257-6261.
[http://dx.doi.org/10.1016/j.tetlet.2015.09.105]
[53]
Khan, K.M.; Saify, Z.S.; Hayat, S.; Khan, M.Z.; Noor, F.; Makhmoor, T.; Choudhary, M.I. Synthesis, antioxidant and insecticidal activities of some coumarin derivatives. J. Chem. Soc. Pak., 2002, 24(3), 226-231.
[54]
Patel, R.V.; Patel, A.B.; Kumari, P.; Chikhalia, K.H. Synthesis of novel 3-(5-sulfanyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one condensed s-triazinylpiperazines and piperidines as antimicrobial agents. Med. Chem. Res., 2012, 21(10), 3119-3132.
[http://dx.doi.org/10.1007/s00044-011-9842-7]
[55]
Ingale, N.; Maddi, V.; Palkar, M.; Ronad, P.; Mamledesai, S.; Vishwanathswamy, A.H.M.; Satyanarayana, D. Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones. Med. Chem. Res., 2012, 21(1), 16-26.
[http://dx.doi.org/10.1007/s00044-010-9494-z]
[56]
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.
[57]
Abate, A.; Dimartino, V.; Spina, P.; Costa, P.L.; Lombardo, C.; Santini, A.; Del Piano, M.; Alimonti, P. Hymecromone in the treatment of motor disorders of the bile ducts: A multicenter, double-blind, placebo-controlled clinical study. Drugs Exp. Clin. Res., 2001, 27(5-6), 223-231.
[PMID: 11951580]
[58]
Opherk, D.; Schuler, G.; Waas, W.; Dietz, R.; Kübler, W. Intravenous carbochromen: A potent and effective drug for estimation of coronary dilatory capacity. Eur. Heart J., 1990, 11(4), 342-347.
[http://dx.doi.org/10.1093/oxfordjournals.eurheartj.a059708] [PMID: 2185023]
[59]
Heide, L. The aminocoumarins: Biosynthesis and biology. Nat. Prod. Rep., 2009, 26(10), 1241-1250.
[http://dx.doi.org/10.1039/b808333a] [PMID: 19779639]
[60]
Wu, L.; Wang, X.; Xu, W.; Farzaneh, F.; Xu, R. The structure and pharmacological functions of coumarins and their derivatives. Curr. Med. Chem., 2009, 16(32), 4236-4260.
[http://dx.doi.org/10.2174/092986709789578187] [PMID: 19754420]
[61]
Keri, R.S.; Sasidhar, B.S.; Nagaraja, B.M.; Santos, M.A. Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents. Eur. J. Med. Chem., 2015, 100(6), 257-269.
[http://dx.doi.org/10.1016/j.ejmech.2015.06.017] [PMID: 26112067]
[62]
Keating, G.J.; O’Kennedy, R. The chemistry and occurrence of coumarins. Coumarins: Biology, Applications and Mode of Action; O’Kennedy, R.; Thornes, R.D; Wiley, Chichester, Ed.; Portsmouth, 1997, pp. 23-66.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 17
ISSUE: 7
Year: 2020
Published on: 08 October, 2020
Page: [780 - 794]
Pages: 15
DOI: 10.2174/1570193X16666191029111051
Price: $65

Article Metrics

PDF: 46
HTML: 3
EPUB: 2
PRC: 2