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Research Articles

Development of novel 1,2,4-triazole containing compounds with anticancer and potent anti-CB1 activity

, , ORCID Icon &
Pages 3862-3873 | Received 30 Nov 2022, Accepted 14 May 2023, Published online: 27 Jul 2023

References

  • Abdelli, A., Azzouni, S., Plais, R., Gaucher, A., Efrit, M. L., & Prim, D. (2021). Recent advances in the chemistry of 1,2,4-triazoles: Synthesis, reactivity and biological activities. Tetrahedron Letters, 86, 153518. https://doi.org/10.1016/j.tetlet.2021.153518
  • Aggarwal, R., & Sumran, G. (2020). An insight on medicinal attributes of 1,2,4-triazoles. European Journal of Medicinal Chemistry, 205, 112652. https://doi.org/10.1016/j.ejmech.2020.112652
  • Akgol, S., Kalkan, B. M., Yucel, D., & Kocabas, F. (2021). SC1 limits tube formation, branching, migration, expansion and induce apoptosis of endothelial cells. Vascular Pharmacology, 141, 106903. https://doi.org/10.1016/j.vph.2021.106903
  • Al-Hussain, S. A., Farghaly, T. A., Zaki, M. E. A., Abdulwahab, H. G., Al-Qurashi, N. T., & Muhammad, Z. A. (2020). Discovery of novel indolyl-1,2,4-triazole hybrids as potent vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitors with potential anti-renal cancer activity. Bioorganic Chemistry, 105, 104330. https://doi.org/10.1016/j.bioorg.2020.104330
  • Ali, J., Camilleri, P., Brown, M. B., Hutt, A. J., & Kirton, S. B. (2012). In silico prediction of aqueous solubility using simple QSPR models: The importance of phenol and phenol-like moieties. Journal of Chemical Information and Modeling, 52(11), 2950–2957. https://doi.org/10.1021/ci300447c
  • Andraos, J. (2005). Unification of reaction metrics for green chemistry: Applications to reaction analysis. Organic Process Research & Development, 9(2), 149–163. https://doi.org/10.1021/op049803n
  • Antenucci, A., Dughera, S., & Renzi, P. (2021). Green chemistry meets asymmetric organocatalysis: A critical overview on catalysts synthesis. ChemSusChem., 14(14), 2785–2853. https://doi.org/10.1002/cssc.202100573
  • Bosier, B., Muccioli, G. G., Hermans, E., & Lambert, D. M. (2010). Functionally selective cannabinoid receptor signalling: Therapeutic implications and opportunities. Biochemical Pharmacology, 80(1), 1–12. https://doi.org/10.1016/j.bcp.2010.02.013
  • Brown, I., Cascio, M. G., Rotondo, D., Pertwee, R. G., Heys, S. D., & Wahle, K. W. J. (2013). Cannabinoids and omega-3/6 endocannabinoids as cell death and anticancer modulators. Progress in Lipid Research, 52(1), 80–109. https://doi.org/10.1016/j.plipres.2012.10.001
  • Cao, X., Wang, W., Wang, S., & Bao, L. (2017). Asymmetric synthesis of novel triazole derivatives and their in vitro antiviral activity and mechanism of action. European Journal of Medicinal Chemistry, 139, 718–725. https://doi.org/10.1016/j.ejmech.2017.08.057
  • Chakravarti, B., Ravi, J., & Ganju, R. K. (2014). Cannabinoids as therapeutic agents in cancer: Current status and future implications. Oncotarget, 5(15), 5852–5872. https://doi.org/10.18632/oncotarget.2233
  • Chu, X.-M., Wang, C., Wang, W.-L., Liang, L.-L., Liu, W., Gong, K.-K., & Sun, K.-L. (2019). Triazole derivatives and their antiplasmodial and antimalarial activities. European Journal of Medicinal Chemistry, 166, 206–223. https://doi.org/10.1016/j.ejmech.2019.01.047
  • Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7, 42717. https://doi.org/10.1038/srep42717
  • Daina, A., & Zoete, V. (2016). A BOILED-Egg to predict gastrointestinal absorption and brain penetration of small molecules. ChemMedChem., 11(11), 1117–1121. https://doi.org/10.1002/cmdc.201600182
  • Deiana, S. (2013). Medical use of cannabis. Cannabidiol: A new light for schizophrenia? Drug Testing and Analysis, 5(1), 46–51. https://doi.org/10.1002/dta.1425
  • Demirci, S., Mermer, A., Ak, G., Aksakal, F., Colak, N., Demirbas, A., Ayaz, F. A., & Demirbas, N. (2017). Conventional and microwave-assisted total synthesis, antioxidant capacity, biological activity, and molecular docking studies of new hybrid compounds. Journal of Heterocyclic Chemistry, 54(3), 1785–1805. https://doi.org/10.1002/jhet.2760
  • 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. https://doi.org/10.1016/j.ejmech.2018.07.024
  • Fan, Y. L., Ke, X., & Liu, M. (2018). Coumarin–triazole hybrids and their biological activities. Journal of Heterocyclic Chemistry, 55(4), 791–802. https://doi.org/10.1002/jhet.3112
  • Gomaa, H. A. M., El-Sherief, H. A. M., Hussein, S., Gouda, A. M., Salem, O. I. A., Alharbi, K. S., Hayallah, A. M., & Youssif, B. G. M. (2020). Novel 1,2,4-triazole derivatives as apoptotic inducers targeting p53: Synthesis and antiproliferative activity. Bioorganic Chemistry, 105, 104369. https://doi.org/10.1016/j.bioorg.2020.104369
  • Grotenhermen, F. (2003). Pharmacokinetics and pharmacodynamics of cannabinoids. Clinical Pharmacokinetics, 42(4), 327–360. https://doi.org/10.2165/00003088-200342040-00003
  • Howlett, A. C. (2005). Cannabinoid receptor signaling. Handbook of Experimental Pharmacology, 168(168), 53–79. https://doi.org/10.1007/3-540-26573-2_2
  • Ikizler, A. A., Ikizler, A., Erdogan, Y., & Serdar, M. (2006). Mass spectra of some 1,2,4-triazoles. Journal of Heterocyclic Chemistry, 24, 423–436. https://doi.org/10.1080/00387019108020667
  • Ikizler, A. A., & Yüksek, H. (1994). Reaction of 4-Amino-4,5-dihydro-1H-1,2,4-triazol-5-ones with 2,5-dimethoxytetrahydrofuran. Collection of Czechoslovak Chemical Communications, 59(3), 731–735. https://doi.org/10.1135/cccc19940731
  • Kaproń, B., Czarnomysy, R., Wysokiński, M., Andrys, R., Musilek, K., Angeli, A., Supuran, C. T., & Plech, T. (2020). 1,2,4-Triazole-based anticonvulsant agents with additional ROS scavenging activity are effective in a model of pharmacoresistant epilepsy. Journal of Enzyme Inhibition and Medicinal Chemistry, 35(1), 993–1002. https://doi.org/10.1080/14756366.2020.1748026
  • Kaur, R., Ranjan Dwivedi, A., Kumar, B., & Kumar, V. (2016). Recent developments on 1,2,4-triazole nucleus in anticancer compounds: A review. Anti-Cancer Agents in Medicinal Chemistry, 16(4), 465–489. https://doi.org/10.2174/1871520615666150819121106
  • Kinen, C. O., Rossi, L. I., & Rossi, R. H. (2009). The development of an environmentally benign sulfide oxidation procedure and its assessment by green chemistry metrics. Green Chemistry, 11(2), 223–228. https://doi.org/10.1039/B815986F
  • Kocabaş, F., & Ergin, E. K. (2016). Identification of small molecule binding pocket for inhibition of Crimean? Congo hemorrhagic fever virus OTU protease. Turkish Journal of Biology, 40(1), 22. https://dergipark.org.tr/en/pub/tbtkbiology/issue/34784/385160.
  • Li, P., Cao, S., Huang, Y., Zhang, Y., Liu, J., Cai, X., Zhou, L., Li, J., Jiang, Z., Ding, L., Zheng, Z., Li, S., & Ye, Q. (2021). A novel chemical inhibitor suppresses breast cancer cell growth and metastasis through inhibiting HPIP oncoprotein. Cell Death Discovery, 7(1), 198. https://doi.org/10.1038/s41420-021-00580-3
  • Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (1997). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 23(1–3), 3–25. https://doi.org/10.1016/S0169-409X(96)00423-1
  • Mangal, N., Erridge, S., Habib, N., Sadanandam, A., Reebye, V., & Sodergren, M. H. (2021). Cannabinoids in the landscape of cancer. Journal of Cancer Research and Clinical Oncology, 147(9), 2507–2534. https://doi.org/10.1007/s00432-021-03710-7
  • McKallip, R. J., Jia, W., Schlomer, J., Warren, J. W., Nagarkatti, P. S., & Nagarkatti, M. (2006). Cannabidiol-induced apoptosis in human leukemia cells: A novel role of cannabidiol in the regulation of p22phox and Nox4 expression. Molecular Pharmacology, 70(3), 897–908. https://doi.org/10.1124/mol.106.023937
  • McKallip, R. J., Nagarkatti, M., & Nagarkatti, P. S. (2005). Δ-9-tetrahydrocannabinol enhances breast cancer growth and metastasis by suppression of the antitumor immune response. Journal of Immunology, 174(6), 3281–3289. https://doi.org/10.4049/jimmunol.174.6.3281
  • Menteşe, E., Güner, A., Polatlı, E., Emirik, M., Bektaş, H., & Kahveci, B. (2021). Synthesis and anticancer activities of some new coumarin derivatives including the triazole ring and their in silico molecular docking studies. Archiv Der Pharmazie, 354(3), e2000284. https://doi.org/10.1002/ardp.202000284
  • Mermer, A., Demirbas, N., Demirbas, A., Colak, N., Ayaz, F. A., Alagumuthu, M., & Arumugam, S. (2018). Synthesis, biological activity and structure activity relationship studies of novel conazole analogues via conventional, microwave and ultrasound mediated techniques. Bioorganic Chemistry, 81, 55–70. https://doi.org/10.1016/j.bioorg.2018.07.036
  • Mermer, A., Faiz, O., Demirbas, A., Demirbas, N., Alagumuthu, M., & Arumugam, S. (2019). Piperazine-azole-fluoroquinolone hybrids: Conventional and microwave irradiated synthesis, biological activity screening and molecular docking studies. Bioorganic Chemistry, 85, 308–318. https://doi.org/10.1016/j.bioorg.2019.01.009
  • Mohassab, A. M., Hassan, H. A., Abdelhamid, D., Gouda, A. M., Youssif, B. G. M., Tateishi, H., Fujita, M., Otsuka, M., & Abdel-Aziz, M. (2021). Design and synthesis of novel quinoline/chalcone/1,2,4-triazole hybrids as potent antiproliferative agent targeting EGFR and BRAF V600E kinases. Bioorganic Chemistry, 106, 104510.
  • Mohire, P. P., Chandam, D. R., Patil, R. B., Patravale, A. A., Ghosh, J. S., & Deshmukh, M. B. (2019). Low melting mixture glycerol: proline as an innovative designer solvent for the synthesis of novel chromeno fused thiazolopyrimidinone derivatives: An excellent correlation with green chemistry metrics. Journal of Molecular Liquids, 283, 69–80. https://doi.org/10.1016/j.molliq.2019.03.058
  • Peyton, L. R., Gallagher, S., & Hashemzadeh, M. (2015). Triazole antifungals: A review. Drugs of Today (Barcelona, Spain: 1998), 51(12), 705–718. https://doi.org/10.1358/dot.2015.51.12.2421058
  • Pokuri, S., Singla, R., Bhat, V., & Shenoy, G. (2014). Insights on the antioxidant potential of 1, 2, 4-triazoles: Synthesis, screening & QSAR studies. Current Drug Metabolism, 15(4), 389–397. https://doi.org/10.2174/1389200215666140908101958
  • Pragathi, Y. J., Sreenivasulu, R., Veronica, D., & Raju, R. R. (2021). Design, synthesis, and biological evaluation of 1,2,4-thiadiazole-1,2,4-triazole derivatives bearing amide functionality as anticancer agents. Arabian Journal for Science and Engineering, 46(1), 225–232. https://doi.org/10.1007/s13369-020-04626-z
  • Sarfaraz, S., Adhami, V. M., Syed, D. N., Afaq, F., & Mukhtar, H. (2008). Cannabinoids for cancer treatment: Progress and promise. Cancer Research, 68(2), 339–342. https://doi.org/10.1158/0008-5472.CAN-07-2785
  • Shahbazi, F., Grandi, V., Banerjee, A., & Trant, J. F. (2020). Cannabinoids and cannabinoid receptors: The story so far. iScience, 23(7), 101301. https://doi.org/10.1016/j.isci.2020.101301
  • Sheldon, R. A., Bode, M. L., & Akakios, S. G. (2022). Metrics of green chemistry: Waste minimization. Current Opinion in Green and Sustainable Chemistry, 33, 100569. https://doi.org/10.1016/j.cogsc.2021.100569
  • Siyah, P., Akgol, S., Durdagi, S., & Kocabas, F. (2021). Identification of first-in-class plasmodium OTU inhibitors with potent anti-malarial activity. Biochemical Journal, 478(18), 3445–3466. https://doi.org/10.1042/BCJ20210481
  • Sung, H., Ferlay, J., Siegel, R. L., Laversanne, M., Soerjomataram, I., Jemal, A., & Bray, F. (2021). Global Cancer Statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA: A Cancer Journal for Clinicians, 71(3), 209–249. https://doi.org/10.3322/caac.21660
  • Tokala, R., Bale, S., Janrao, I. P., Vennela, A., Kumar, N. P., Senwar, K. R., Godugu, C., & Shankaraiah, N. (2018). Synthesis of 1,2,4-triazole-linked urea/thiourea conjugates as cytotoxic and apoptosis inducing agents. Bioorganic & Medicinal Chemistry Letters, 28(10), 1919–1924. https://doi.org/10.1016/j.bmcl.2018.03.074
  • Tomiyama, K., & Funada, M. (2011). Cytotoxicity of synthetic cannabinoids found in ‘Spice’ products: The role of cannabinoid receptors and the caspase cascade in the NG 108-15 cell line. Toxicology Letters, 207(1), 12–17. https://doi.org/10.1016/j.toxlet.2011.08.021
  • Turan, R. D., Albayrak, E., Uslu, M., Siyah, P., Alyazici, L. Y., Kalkan, B. M., Aslan, G. S., Yucel, D., Aksoz, M., Tuysuz, E. C., Meric, N., Durdagi, S., Gulbas, Z., & Kocabas, F. (2020). Development of small molecule MEIS inhibitors that modulate HSC activity. Scientific Reports, 10(1), 7994.https://doi.org/10.1038/s41598-020-64888-3
  • Understanding Cancer-NIH Curriculum Supplement Series-NCBI Bookshelf. https://www.ncbi.nlm.nih.gov/books/NBK20362/.
  • Yang, F., Chen, L., Lai, J.-M., Jian, X.-E., Lv, D.-X., Yuan, L.-L., Liu, Y.-X., Liang, F.-T., Zheng, X.-L., Li, X.-L., Wei, L.-Y., You, W.-W., & Zhao, P.-L. (2021). Synthesis, biological evaluation, and structure-activity relationships of new tubulin polymerization inhibitors based on 5-amino-1,2,4-triazole scaffold. Bioorganic and Medicinal Chemistry Letters, 38, 127880.
  • Zhou, C.-H., & Wang, Y. (2012). Recent researches in triazole compounds as medicinal drugs. Current Medicinal Chemistry, 19(2), 239–280. https://doi.org/10.2174/092986712803414213

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