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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

1,2,4-Triazole-conjugated Fluoroquinolones as Potential Candidates for New Antibacterial Agents

Author(s): Yıldız Uygun Cebeci* and Sengul Alpay Karaoglu

Volume 21, Issue 8, 2024

Published on: 24 January, 2024

Page: [669 - 676] Pages: 8

DOI: 10.2174/0115701786270260231215101046

Price: $65

Abstract

In this study, synthesis of 1,2,4 triazole-fluoroquinolone hybrid compounds was realized. 7a-d hybrid compound was obtained as a result of mannich reaction with 6a-b triazole compounds norfloxacin and ciprofloxacin. 1H-NMR, 13C-NMR, Mass Spectrometry and Elemental Analysis confirmed the structures of all synthesized compounds. The antimicrobial activities of all compounds were investigated, and it was observed that 7a-d compounds, which are mannich bases, showed excellent activity.

Graphical Abstract

[1]
Kerru, N.; Gummidi, L.; Maddila, S.; Gangu, K.K.; Jonnalagadda, S.B. Molecules, 2020, 25(8), 1909.
[http://dx.doi.org/10.3390/molecules25081909] [PMID: 32326131]
[2]
Lang, D.K. Med. Chem., 2020, 20(18), 2150-2168.
[3]
Henary, M.; Kananda, C.; Rotolo, L.; Savino, B.; Owens, E.A.; Cravotto, G. RSC Advances, 2020, 10(24), 14170-14197.
[http://dx.doi.org/10.1039/D0RA01378A] [PMID: 35498463]
[4]
Gomha, S.M.; Farghaly, T.A.; Sayed, A.R. J. Heterocycl. Chem., 2017, 54(2), 1537-1542.
[http://dx.doi.org/10.1002/jhet.2741]
[5]
Hassan, A.Y.; Sarg, M.T.; Hussein, E.M. J. Heterocycl. Chem., 2019, 56(4), 1437-1457.
[http://dx.doi.org/10.1002/jhet.3524]
[6]
Chate, A.V.; Kamdi, S.P.; Bhagat, A.N.; Jadhav, C.K.; Nipte, A.; Sarkate, A.P.; Tiwari, S.V.; Gill, C.H. J. Heterocycl. Chem., 2018, 55(10), 2297-2302.
[http://dx.doi.org/10.1002/jhet.3286]
[7]
Bhat, H.R.; Masih, A.; Shakya, A.; Ghosh, S.K.; Singh, U.P. J. Heterocycl. Chem., 2020, 57(1), 390-399.
[http://dx.doi.org/10.1002/jhet.3791]
[8]
Liu, J.C.; Narva, S.; Zhou, K.; Zhang, W. Mini Rev. Med. Chem., 2019, 19(18), 1517-1530.
[http://dx.doi.org/10.2174/1389557519666190312152358] [PMID: 30864519]
[9]
Santana, A.C.; Silva Filho, R.C.; Menezes, J.C.J.M.D.S.; Allonso, D.; Campos, V.R. Life, 2020, 11(1), 16.
[http://dx.doi.org/10.3390/life11010016] [PMID: 33396631]
[10]
Bianco, M.C.A.D.; Marinho, D.I.L.F.; Hoelz, L.V.B.; Bastos, M.M.; Boechat, N. Pharmaceuticals, 2021, 14(9), 893.
[http://dx.doi.org/10.3390/ph14090893] [PMID: 34577593]
[11]
Shabalin, D.A.; Camp, J.E. Org. Biomol. Chem., 2020, 18(21), 3950-3964.
[http://dx.doi.org/10.1039/D0OB00350F] [PMID: 32419000]
[12]
Sharma, P.; LaRosa, C.; Antwi, J.; Govindarajan, R.; Werbovetz, K.A. Molecules, 2021, 26(14), 4213.
[http://dx.doi.org/10.3390/molecules26144213] [PMID: 34299488]
[13]
Xu, M.; Peng, Y.; Zhu, L.; Wang, S.; Ji, J.; Rakesh, K.P. Eur. J. Med. Chem., 2019, 180, 656-672.
[http://dx.doi.org/10.1016/j.ejmech.2019.07.059] [PMID: 31352246]
[14]
Strzelecka, M. Świątek, P. Pharmaceuticals, 2021, 14(3), 224.
[http://dx.doi.org/10.3390/ph14030224] [PMID: 33799936]
[15]
Dixit, D.; Verma, P.K.; Marwaha, R.K. J. Indian Chem. Soc., 2021, 18(10), 2535-2565.
[http://dx.doi.org/10.1007/s13738-021-02231-x]
[16]
Jain, A.; Piplani, P. Mini Rev. Med. Chem., 2019, 19(16), 1298-1368.
[http://dx.doi.org/10.2174/1389557519666190312162601] [PMID: 30864516]
[17]
Poonia, N.; Kumar, A.; Kumar, V.; Yadav, M.; Lal, K. Curr. Top. Med. Chem., 2021, 21(23), 2109-2133.
[http://dx.doi.org/10.2174/1568026621666210913122828] [PMID: 34517801]
[18]
Czyrski, A. Resztak, M.; Świderski, P.; Brylak, J.; Główka, F.K. Pharmaceutics, 2021, 13(11), 1961.
[http://dx.doi.org/10.3390/pharmaceutics13111961] [PMID: 34834376]
[19]
Sahu, J.K.; Ganguly, S.; Kaushik, A. Chin. J. Nat. Med., 2013, 11(5), 456-465.
[http://dx.doi.org/10.1016/S1875-5364(13)60084-9] [PMID: 24359767]
[20]
Shalini, K. J. Org. Chem., 2011, 7, 668-677.
[21]
Gadhave, P.P. Ann. Biol. Res., 2010, 82-89.
[22]
Pibiri, I.; Buscemi, S. Curr. Bioact. Compd., 2010, 6(4), 208-242.
[http://dx.doi.org/10.2174/157340710793237281]
[23]
Kumar, A.; Saxena, N.; Mehrotra, A.; Srivastava, N. Curr. Org. Chem., 2020, 24(8), 817-854.
[http://dx.doi.org/10.2174/1385272824999200427082108]
[24]
Pham, T.D.M.; Ziora, Z.M.; Blaskovich, M.A.T. MedChemComm, 2019, 10(10), 1719-1739.
[http://dx.doi.org/10.1039/C9MD00120D] [PMID: 31803393]
[25]
Chu, X.M.; Wang, C.; Liu, W.; Liang, L.L.; Gong, K.K.; Zhao, C.Y.; Sun, K.L. Eur. J. Med. Chem., 2019, 161, 101-117.
[http://dx.doi.org/10.1016/j.ejmech.2018.10.035] [PMID: 30343191]
[26]
Cui, S.F.; Peng, L.P.; Zhang, H.Z.; Rasheed, S.; Vijaya Kumar, K.; Zhou, C.H. Eur. J. Med. Chem., 2014, 86, 318-334.
[http://dx.doi.org/10.1016/j.ejmech.2014.08.063] [PMID: 25173851]
[27]
Zhang, G.F.; Zhang, S.; Pan, B.; Liu, X.; Feng, L.S. Eur. J. Med. Chem., 2018, 143, 710-723.
[http://dx.doi.org/10.1016/j.ejmech.2017.11.082] [PMID: 29220792]
[28]
Fedorowicz, J. Monatsh. Chem., 2018, 149, 1199-1245.
[http://dx.doi.org/10.1007/s00706-018-2215-x] [PMID: 29983452]
[29]
Gao, C.; Fan, Y.L.; Zhao, F.; Ren, Q.C.; Wu, X.; Chang, L.; Gao, F. Eur. J. Med. Chem., 2018, 157, 1081-1095.
[http://dx.doi.org/10.1016/j.ejmech.2018.08.061] [PMID: 30179746]
[30]
Uygun, C. Y, J. Iran. Chem. Soc., 2023, 20, 1085-1094.
[31]
Althagafi, I.I.; Shaaban, M.R. J. Mol. Struct., 2017, 1142, 122-129.
[http://dx.doi.org/10.1016/j.molstruc.2017.04.047]
[32]
Ashok, M.; Holla, B.S.; Poojary, B. Eur. J. Med. Chem., 2007, 42(8), 1095-1101.
[http://dx.doi.org/10.1016/j.ejmech.2007.01.015] [PMID: 17346860]
[33]
Bayrak, H.; Demirbas, A.; Karaoglu, S.A.; Demirbas, N. Eur. J. Med. Chem., 2009, 44(3), 1057-1066.
[http://dx.doi.org/10.1016/j.ejmech.2008.06.019] [PMID: 18676062]
[34]
Karthikeyan, M.S.; Prasad, D.J.; Poojary, B.; Subrahmanya Bhat, K.; Holla, B.S.; Kumari, N.S. Bioorg. Med. Chem., 2006, 14(22), 7482-7489.
[http://dx.doi.org/10.1016/j.bmc.2006.07.015] [PMID: 16879972]
[35]
Demirbas, A.; Sahin, D.; Demirbas, N.; Karaoglu, S.A. Eur. J. Med. Chem., 2009, 44(7), 2896-2903.
[http://dx.doi.org/10.1016/j.ejmech.2008.12.005] [PMID: 19167136]
[36]
Shi, J.; Ding, M.; Luo, N.; Wan, S.; Li, P.; Li, J.; Bao, X. J. Agric. Food Chem., 2020, 68(36), 9613-9623.
[http://dx.doi.org/10.1021/acs.jafc.0c01365] [PMID: 32786823]
[37]
Almajan, G.L.; Barbuceanu, S.F.; Almajan, E.R.; Draghici, C.; Saramet, G. Eur. J. Med. Chem., 2009, 44(7), 3083-3089.
[http://dx.doi.org/10.1016/j.ejmech.2008.07.003] [PMID: 18708273]
[38]
Sridhar, S.K.; Saravanan, M. Eur. J. Med. Chem., 2001, 36, 615-625.
[http://dx.doi.org/10.1016/S0223-5234(01)01255-7] [PMID: 11600231]
[39]
Isloor, A.M.; Kalluraya, B.; Shetty, P. Eur. J. Med. Chem., 2009, 44(9), 3784-3787.
[http://dx.doi.org/10.1016/j.ejmech.2009.04.038] [PMID: 19464087]
[40]
Roman, G. Eur. J. Med. Chem., 2015, 89, 743-816.
[http://dx.doi.org/10.1016/j.ejmech.2014.10.076] [PMID: 25462280]
[41]
Turan-Zitouni, G. Kaplancıklı, Z.A.; Yıldız, M.T.; Chevallet, P.; Kaya, D. Eur. J. Med. Chem., 2005, 40(6), 607-613.
[http://dx.doi.org/10.1016/j.ejmech.2005.01.007] [PMID: 15922844]
[42]
Shafiee, A.; Sayadi, A.; Roozbahani, M.H.; Foroumadi, A.; Kamal, F. Arch. Pharm., 2002, 335(10), 495-499.
[http://dx.doi.org/10.1002/ardp.200290004] [PMID: 12506398]
[43]
Eswaran, S.; Adhikari, A.V.; Shetty, N.S. Eur. J. Med. Chem., 2009, 44(11), 4637-4647.
[http://dx.doi.org/10.1016/j.ejmech.2009.06.031] [PMID: 19647905]
[44]
Plech, T.; Wujec, M.; Majewska, M.; Kosikowska, U.; Malm, A. Med. Chem. Res., 2013, 22(5), 2531-2537.
[http://dx.doi.org/10.1007/s00044-012-0248-y] [PMID: 23543889]
[45]
Ammar, U.M.; Abdel-Maksoud, M.S.; Oh, C.H. Eur. J. Med. Chem., 2018, 158, 144-166.
[http://dx.doi.org/10.1016/j.ejmech.2018.09.005] [PMID: 30216849]
[46]
Sriram, D.; Yogeeswari, P.; Reddy, S.P. Bioorg. Med. Chem. Lett., 2006, 16(8), 2113-2116.
[http://dx.doi.org/10.1016/j.bmcl.2006.01.064] [PMID: 16464574]
[47]
Allemann, C.; Gordillo, R.; Clemente, F.R.; Cheong, P.H.Y.; Houk, K.N. Acc. Chem. Res., 2004, 37(8), 558-569.
[http://dx.doi.org/10.1021/ar0300524] [PMID: 15311955]
[48]
Notz, W.; Tanaka, F.; Barbas, C.F., III Acc. Chem. Res., 2004, 37(8), 580-591.
[http://dx.doi.org/10.1021/ar0300468] [PMID: 15311957]
[49]
(a) Muller, R.; Goesmann, H.; Waldmann, H. Angew. Chem. Int. Ed., 1999, 38, 184-187.;
(b) Angew. Chem., 1999, 111, 166-169.
[50]
Tramontini, M.; Angiolini, L. Tetrahedron, 1990, 46(6), 1791-1837.
[http://dx.doi.org/10.1016/S0040-4020(01)89752-0]
[51]
Basoglu Ozdemir, S.; Cebeci Uygun, Y.; Bayrak, H.; Mermer, A.; Ceylan, S.; Demirbas, A. Heterocycl. Commun., 2017, 23(1), 43-54.
[http://dx.doi.org/10.1515/hc-2016-0125]
[52]
Johansen, M.; Bundgaard, H. Arch. Pharm. Chemi Sci. Ed., 1982, 10, 111-121.
[53]
Cabrera Perez, M.; Gonzalez Daz, A.H.; Fernandez Teruel, C. PlaDelfina, J. M.; Bermejo Sanz, M. Eur. J. Pharm. Biopharm., 2002, 53, 317-325.
[PMID: 11976020]
[54]
Barbachyn, M. R.; Brickner, S. J.; Cleek, G. J.; Gadwood, R. C.; Greg, K. C.; Hendges, S. K. The Royal Society of Chemistry; Hartnolls: Bodmin 1997.
[55]
Ceylan, S.; Bektas, H.; Bayrak, H.; Demirbas, N.; Alpay-Karaoglu, S.; Ulker, S. Pharm. Chem. Life Sci., 2013, 346, 743-756.
[http://dx.doi.org/10.1002/ardp.201300161]
[56]
Demirbas, N.; Karaoglu, S.A.; Demirbas, A.; Çelik, E. ARKIVOC, 2005, 2005(1), 75-91.
[http://dx.doi.org/10.3998/ark.5550190.0006.108]
[57]
Demirci, S.; Mermer, A.; Ak, G.; Aksakal, F.; Çolak, N.; Demirbas, A.; Ayaz, F.A.; Demirbas, N. J. Heterocycl. Chem., 2017, 54(3), 1785-1805.
[http://dx.doi.org/10.1002/jhet.2760]
[58]
Uygun Cebeci, Y.; Ceylan, S.; Altun, M.; Alpay-Karaoglu, S. ChemistrySelect, 2023, 8(e202300385), 1-9.
[59]
Akshatha, N.; Manohara, D.J.; Yashoda, M.P.; Kakarla, R.R.; Anjanapura, V.R. J. Microbiol. Methods, 2019, 163, 105650.
[http://dx.doi.org/10.1016/j.mimet.2019.105650] [PMID: 31176650]

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