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Research Articles

Synthesis, characterization and anti-inflammatory activity evaluation of 1,2,4-triazole and its derivatives as a potential scaffold for the synthesis of drugs against prostaglandin-endoperoxide synthase

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Pages 457-475 | Received 12 Nov 2019, Accepted 26 Dec 2019, Published online: 10 Jan 2020

References

  • Afonso, V., Champy, R., Mitrovic, D., Collin, P., & Lomri, A. (2007). Reactive oxygen species and superoxide dismutases: Role in joint diseases. Joint Bone Spine, 74(4), 324–329. doi:10.1016/j.jbspin.2007.02.002
  • Basri, A. M., Taha, H., & Ahmad, N. (2017). A review on the pharmacological activities and phytochemicals of Alpinia officinarum (galangal) extracts derived from bioassay-guided fractionation and isolation. Pharmacognosy Reviews, 11(21), 43–56. doi:10.4103/phrev.phrev_55_16
  • Bogolubsky, A. V., Moroz, Y. S., Mykhailiuk, P. K., Ostapchuk, E. N., Rudnichenko, A. V., Dmytriv, Y. V., … Tolmachev, A. (2015). One-pot parallel synthesis of alkyl sulfides, sulfoxides, and sulfones. ACS Combinatorial Science, 17(6), 348–354. doi:10.1021/acscombsci.5b00024
  • Dheer, D., Singh, V., & Shankar, R. (2017). Medicinal attributes of 1,2,3-triazoles: Current developments. Bioorganic Chemistry, 71, 30–54. doi:10.1016/j.bioorg.2017.01.010
  • El-Sherief, H. A. M., Youssif, B. G. M., Abbas Bukhari, S. N., Abdelazeem, A. H., Abdel-Aziz, M., & Abdel-Rahman, H. M. (2018). Synthesis, anticancer activity and molecular modeling studies of 1,2,4-triazole derivatives as EGFR inhibitors. European Journal of Medicinal Chemistry, 156, 774–789. doi:10.1016/j.ejmech.2018.07.024
  • Eswaran, S., Adhikari, A. V., & Shetty, N. S. (2009). Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. European Journal of Medicinal Chemistry, 44(11), 4637–4647. doi:10.1016/j.ejmech.2009.06.031
  • Fan, Y.-L., Ke, X., & Liu, M. (2018). Coumarin-triazole hybrids and their biological activities. Journal of Heterocyclic Chemistry, 55(4), 791–802. doi:10.1002/jhet.3112
  • Fan, Z., Shi, J., & Bao, X. (2018). Synthesis and antimicrobial evaluation of novel 1,2,4-triazole thioether derivatives bearing a quinazoline moiety. Molecular Diversity, 22(3), 657–667. doi:10.1007/s11030-018-9821-8
  • Gajanan Khanage, S., Raju, A., Baban Mohite, P., & Bhanudas Pandhare, R. (2013). Analgesic activity of some 1,2,4-triazole heterocycles clubbed with pyrazole, tetrazole, isoxazole and pyrimidine. Advanced Pharmaceutical Bulletin, 3(1), 13–18. doi:10.5681/apb.2013.003
  • Gao, C., Chang, L., Xu, Z., Yan, X.-F., Ding, C., Zhao, F., … Feng, L.-S. (2019). Recent advances of tetrazole derivatives as potential anti-tubercular and anti-malarial agents. European Journal of Medicinal Chemistry, 163, 404–412. doi:10.1016/j.ejmech.2018.12.001
  • Gao, F., Wang, T., Xiao, J., & Huang, G. (2019). Antibacterial activity study of 1,2,4-triazole derivatives. European Journal of Medicinal Chemistry, 173, 274–281. doi:10.1016/j.ejmech.2019.04.043
  • Genc, M., Karagoz Genc, Z., Tekin, S., Sandal, S., Sirajuddin, M., Hadda Taibi, B., & Sekerci, M. (2016). Design, synthesis, in vitro antiproliferative activity, binding modeling of 1,2,4,-triazoles as new anti-breast cancer agents. Acta Chimica Slovenica, 63(4), 726–737. doi:10.17344/acsi.2016.2428
  • Hu, J., Wang, Y., Wei, X., Wu, X., Chen, G., Cao, G., … Li, X. (2013). Synthesis and biological evaluation of novel thiazolidinone derivatives as potential anti-inflammatory agents. European Journal of Medicinal Chemistry, 64, 292–301. doi:10.1016/j.ejmech.2013.04.010
  • Jin, R. Y., Zeng, C. Y., Liang, X. H., Sun, X. H., Liu, Y. F., Wang, Y. Y., & Zhou, S. (2018). Design, synthesis, biological activities and DFT calculation of novel 1,2,4-triazole Schiff base derivatives. Bioorganic Chemistry, 80, 253–260. doi:10.1016/j.bioorg.2018.06.030
  • Kandile, N. G., Mohamed, M. I., & Ismaeel, H. M. (2017). Synthesis of new Schiff bases bearing 1,2,4-triazole, thiazolidine and chloroazetidine moieties and their pharmacological evaluation. Journal of Enzyme Inhibition and Medicinal Chemistry, 32(1), 119–129. doi:10.1080/14756366.2016.1238365
  • Kane, J. M., Dudley, M. W., Sorensen, S. M., & Miller, F. P. (1988). 2,4-Dihydro-3H-1,2,4-triazole-3-thiones as potential antidepressant agents. Journal of Medicinal Chemistry, 31(6), 1253–1258. doi:10.1021/jm00401a031
  • Kapron, B., Luszczki, J. J., Plazinska, A., Siwek, A., Karcz, T., Grybos, A., … Plech, T. (2019). Development of the 1,2,4-triazole-based anticonvulsant drug candidates acting on the voltage-gated sodium channels. Insights from in-vivo, in-vitro, and in-silico studies. European Journal of Pharmaceutical Sciences, 129, 42–57. doi:10.1016/j.ejps.2018.12.018
  • Kucukguzel, I., Tatar, E., Kucukguzel, S. G., Rollas, S., & De Clercq, E. (2008). Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. European Journal of Medicinal Chemistry, 43(2), 381–392. doi:10.1016/j.ejmech.2007.04.010
  • Li, Y. H., Zhang, B., Yang, H. K., Li, Q., Diao, P. C., You, W. W., & Zhao, P. L. (2017). Design, synthesis, and biological evaluation of novel alkylsulfanyl-1,2,4-triazoles as cis-restricted combretastatin A-4 analogues. European Journal of Medicinal Chemistry, 125, 1098–1106. doi:10.1016/j.ejmech.2016.10.051
  • Manzocco, L., Anese, M., & Nicoli, M. C. (1998). Antioxidant properties of tea extracts as affected by processing. LWT - Food Science and Technology, 31(7–8), 694–698. doi:10.1006/fstl.1998.0491
  • Morris, G. M., Goodsell, D. S., Halliday, D. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Automated docking using a Lamarckian genetic. Journal of Computational Chemistry, 19(14), 1639–1662. doi:10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
  • Mur Blanch, N., Chabot, G. G., Quentin, L., Scherman, D., Bourg, S., & Dauzonne, D. (2012). In vitro and in vivo biological evaluation of new 4,5-disubstituted 1,2,3-triazoles as cis-constrained analogs of combretastatin A4. European Journal of Medicinal Chemistry, 54, 22–32. doi:10.1016/j.ejmech.2012.04.017
  • Oyaizu, M. (1986). Studies on products of browning reaction–antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44, 307–315. doi:10.5264/eiyogakuzashi.44.307
  • Pan, X., Cao, X., Li, N., Xu, Y., Wu, Q., Bai, J., … Lan, L. (2014). Forsythin inhibits lipopolysaccharide-induced inflammation by suppressing JAK-STAT and p38 MAPK signalings and ROS production. Inflammation Research, 63(7), 597–608. doi:10.1007/s00011-014-0731-7
  • Papadopoulou, M. V., Bloomer, W. D., Rosenzweig, H. S., Chatelain, E., Kaiser, M., Wilkinson, S. R., … Ioset, J.-R. (2012). Novel 3-nitro-1H-1,2,4-triazole-based amides and sulfonamides as potential antitrypanosomal agents. Journal of Medicinal Chemistry, 55(11), 5554–5565. doi:10.1021/jm300508n
  • Paprocka, R., Wiese, M., Eljaszewicz, A., Helmin-Basa, A., Gzella, A., Modzelewska-Banachiewicz, B., & Michalkiewicz, J. (2015). Synthesis and anti-inflammatory activity of new 1,2,4-triazole derivatives. Bioorganic & Medicinal Chemistry Letters, 25(13), 2664–2667. doi:10.1016/j.bmcl.2015.04.079
  • Pastor, R. W., Brooks, B. R., & Szabo, A. (1988). An analysis of the accuracy of Langevin and molecular dynamics algorithm. Molecular Physics, 65(6), 1409–1419. doi:10.1080/00268978800101881
  • Pokuri, S., Singla, R. K., Bhat, V. G., & Shenoy, G. G. (2014). Insights on the antioxidant potential of 1, 2, 4-triazoles: Synthesis, screening & QSAR studies. Current Drug Metabolism, 15(4), 389–397. doi: CDM-EPUB-62195 [pii] doi:10.2174/1389200215666140908101958
  • Routray, I., & Ali, S. (2019). Boron inhibits apoptosis in hyperapoptosis condition: Acts by stabilizing the mitochondrial membrane and inhibiting matrix remodeling. Biochimica et Biophysica Acta (BBA) - General Subjects, 1863(1), 144–152. doi:10.1016/j.bbagen.2018.10.007
  • Shahzad, S. A., Yar, M., Khan, Z. A., Shahzadi, L., Naqvi, S. A. R., Mahmood, A., … Bajda, M. (2019). Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs. Bioorganic Chemistry, 85, 209–220. doi:10.1016/j.bioorg.2019.01.005
  • Shinkafi, T. S., Kaushik, A., Mahmood, A., Tiwari, A. K., Alam, M. M., Akhter, M., … Ali, S. (2019). Computational prediction and experimental validation of the activator function of C2-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone on pancreatic and hepatic hexokinase. Journal of Biomolecular Structure and Dynamics, 1–12. doi:10.1080/07391102.2019.1650829
  • Temraz, A., & El-Tantawy, W. H. (2008). Characterization of antioxidant activity of extract from Artemisia vulgaris. Pakistan Journal of Pharmaceutical Sciences, 21(4), 321–326.
  • Teng, P., Liu, H.-L., Zhang, L., Feng, L.-L., Huai, Y., Deng, Z.-S., … Li, J.-X. (2012). Synthesis and biological evaluation of novel sinomenine derivatives as anti-inflammatory agents. European Journal of Medicinal Chemistry, 50, 63–74. doi:10.1016/j.ejmech.2012.01.036
  • Timur, I., Kocyigit, U. M., Dastan, T., Sandal, S., Ceribasi, A. O., Taslimi, P., … Ciftci, M. (2018). In vitro cytotoxic and in vivo antitumoral activities of some aminomethyl derivatives of 2,4-dihydro-3H-1,2,4-triazole-3-thiones-evaluation of their acetylcholinesterase and carbonic anhydrase enzymes inhibition profiles. Journal of Biochemical and Molecular Toxicology, e22239. doi:10.1002/jbt.22239
  • Uberuaga, B. P., Anghel, M., & Voter, A. F. (2004). Synchronization of trajectories in canonical molecular-dynamics simulations: Observation, explanation, and exploitation. Journal of Chemical Physics, 120(14), 6363–6374. doi:10.1063/1.1667473
  • Wani, M. Y., Bhat, A. R., Azam, A., & Athar, F. (2013). Nitroimidazolyl hydrazones are better amoebicides than their cyclized 1,3,4-oxadiazoline analogues: In vitro studies and lipophilic efficiency analysis. European Journal of Medicinal Chemistry, 64, 190–199. doi:10.1016/j.ejmech.2013.03.034
  • Winter, C. A., Risley, E. A., & Nuss, G. W. (1962). Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Experimental Biology and Medicine, 111(3), 544–547. doi:10.3181/00379727-111-27849
  • Xiao, Z.-P., Wang, X.-D., Wang, P.-F., Zhou, Y., Zhang, J.-W., Zhang, L., … Zhu, H.-L. (2014). Design, synthesis, and evaluation of novel fluoroquinolone-flavonoid hybrids as potent antibiotics against drug-resistant microorganisms. European Journal of Medicinal Chemistry, 80, 92–100. doi:10.1016/j.ejmech.2014.04.037
  • Zhang, H. Z., Damu, G. L. V., Cai, G. X., & Zhou, C. H. (2014). Current developments in the syntheses of 1,2,4-triazole compounds. Current Organic Chemistry, 18(3), 359–406. doi:10.2174/13852728113179990025
  • Zhang, J., Wang, S., Ba, Y., & Xu, Z. (2019). 1,2,4-Triazole-quinoline/quinolone hybrids as potential anti-bacterial agents. European Journal of Medicinal Chemistry, 174, 1–8. doi:10.1016/j.ejmech.2019.04.033
  • Zhang, Q., Peng, Y., Wang, X. I., Keenan, S. M., Arora, S., & Welsh, W. J. (2007). Highly potent triazole-based tubulin polymerization inhibitors. Journal of Medicinal Chemistry, 50(4), 749–754. doi:10.1021/jm061142s
  • Zhang, S., Xu, Z., Gao, C., Ren, Q. C., Chang, L., Lv, Z. S., & Feng, L. S. (2017). Triazole derivatives and their anti-tubercular activity. European Journal of Medicinal Chemistry, 138, 501–513. doi: S0223-5234(17)30505-6 [pii] doi:10.1016/j.ejmech.2017.06.051

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