202
Views
2
CrossRef citations to date
0
Altmetric
Research Articles

Design and Click Synthesis of Novel 1- Substituted-4-(3,4-Dimethoxyphenyl)-1H-1,2,3-Triazole Hybrids for Anticancer Evaluation and Molecular Docking

ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon
Pages 7547-7564 | Received 24 Aug 2022, Accepted 12 Oct 2022, Published online: 27 Oct 2022

References

  • Y.J. Pragathi, R. Sreenivasulu, D. Veronica, and R.R. Raju, “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, no. 1 (2021): 225–32.
  • A. Jemal, F. Bray, M.M. Center, J. Ferlay, E. Ward, and D. Forman, “Global Cancer Statistics,” CA: A Cancer Journal for Clinicians 61, no. 2 (2011): 69–90.
  • S.K. Park, L.Y. Cho, J.J. Yang, B. Park, S.H. Chang, K.S. Lee, H. Kim, K.Y. Yoo, and C.T. Lee, Scientific Committee, Korean Academy of Tuberculosis and Respiratory Diseases, “Lung Cancer Risk and Cigarette Smoking, Lung Tuberculosis according to Histologic Type and Gender in a Population Based Case-Control Study,” Lung Cancer 68, no. 1 (2010): 20–6.
  • M.K. Meffert, J.M. Chang, B.J. Wiltgen, M.S. Fanselow, and D. Baltimore, “NF-Kappa B Functions in Synaptic Signalling and Behaviour,” Nature Neuroscience 6, no. 10 (2003): 1072–8.
  • M.R. Clemens, “Free Radicals in Chemical Carcinogenesis,” Klinische Wochenschrift 69, no. 21–23 (1991): 1123–34.
  • A. Mantovani, P. Allavena, A. Sica, and F. Balkwill, “Cancer-Related Inflammation,” Nature 454, no. 7203 (2008): 436–44.
  • P.E. Clayton, I. Banerjee, P.G. Murray, and A.G. Renehan, “Growth Hormone, the Insulin-like Growth Factor Axis, Insulin and Cancer Risk,” Nature Reviews. Endocrinology 7, no. 1 (2011): 11–24.
  • C. Porta, E. Riboldi, and A. Sica, “Mechanisms Linking Pathogensassociated Inflammation and Cancer,” Cancer Letters 305, no. 2 (2011): 250–62.
  • F.A. Khan, S.S. Akhtar, and M.K. Sheikh, “Cancer Treatment—Objectives and Quality of Life Issues,” The Malaysian Journal of Medical Sciences 12, no. 1 (2005): 3–5.
  • E. Menta and M. Palumbo, “Novel Antineoplastic Agents,” Expert Opinion on Therapeutic Patents 7, no. 12 (1997): 1401–26.
  • S. Nussbaumer, P. Bonnabry, J.-L. Veuthey, and S. Fleury-Souverain, “Analysis of Anticancer Drugs: A Review,” Talanta 85, no. 5 (2011): 2265–89.
  • M. Rebucci and C. Michiels, “Molecular Aspects of Cancer Cell Resistance to Chemotherapy,” Biochemical Pharmacology 85, no. 9 (2013): 1219–26.
  • C. Holohan, S. Van Schaeybroeck, D.B. Longley, and P.G. Johnston, “Cancer Drug Resistance: An Evolving Paradigm,” Nature Reviews Cancer 13, no. 10 (2013): 714–26.
  • R. Rosa, F. Monteleone, N. Zambrano, and R. Bianco, “In Vitro and in Vivo Models for Analysis of Resistance to Anticancer Molecular Molecular Therapies,” Current Medicinal Chemistry 21, no. 14 (2014): 1595–606.
  • M.S. Reddy, N.S. Thirukovela, S. Narsimha, M. Ravinder, and S.K. Nukala, “Synthesis of Fused 1,2,3-Triazoles of Clioquinol via Sequential CuAAC and C –H Arylation; In Vitro Anticancer Activity, in Silico DNA Topoisomerase II Inhibitory Activity and ADMET,” Journal of Molecular Structure 1250 (2022): 131747.
  • U.M. Ammar, M.S. Abdel-Maksoud, and C.H. Oh, “Recent Advances of RAF (Rapidly Accelerated Fibrosarcoma) Inhibitors as anti-Cancer Agents,” European Journal of Medicinal Chemistry 158 (2018): 144–66.
  • F. Gao, X. Zhang, T. Wang, and J. Xiao, “Quinolone Hybrids and Their Anti-Cancer Activities: An Overview,” European Journal of Medicinal Chemistry 165 (2019): 59–79.
  • C. Zhuang, X. Guan, H. Ma, H. Cong, W. Zhang, and Z. Miao, “Small Molecule-Drug Conjugates: A Novel Strategy for Cancer-Targeted Treatment,” European Journal of Medicinal Chemistry 163 (2019): 883–95.
  • K. Suryanarayana, S. Maddila, K. Nagaraju, and S.B. Jonnalagadda, “Design, Synthesis, Docking Study and Biological Evaluation of Novel Thieno[2,3-d]Pyrimidine Tethered 1,2,3-Triazole Scaffolds,” Journal of Molecular Structure 1250 (2022): 131713.
  • Z. Xu, S.J. Zhao, and Y. Liu, “1,2,3-Triazole-Containing Hybrids as Potential Anticancer Agents: Current Developments, Action Mechanisms and Structure-Activity Relationships,” European Journal of Medicinal Chemistry 183 (2019): 111700.
  • S. G. Agalave, S. R. Maujan, and V. S. Pore, “Click Chemistry: 1,2,3-Triazoles as Pharmacophores,” Chemistry an Asian Journal 6, no. 10 (2011): 2696–718.
  • T. El Malah, R.E. Abdel Mageid, H.M. Awad, and H.F. Nour, “Copper(i)-Catalysed Azide–Alkyne Cycloaddition and Antiproliferative Activity of Mono- and Bis-1,2,3-Triazole Derivatives,” New Journal of Chemistry 44, no. 42 (2020): 18256–63.
  • T. El Malah, H.F. Nour, O. Dehbi, F.M.E. Abdel-Megeid, A.E.E.-D. Mahmoud, M.M. Ali, and S.M. Soliman, “Click Synthesis, Anticancer Activity and Molecular Docking Studies on Pyridazinone Scaffolds,” Current Organic Chemistry 22, no. 23 (2018): 2300–7.
  • T. El Malah, H.F. Nour, A.A. Nayl, R.A. El Khashab, F.M.E. Abdel-Megeid, and M.M. Ali, “Anticancer Evaluation of Tris(Triazolyl)Triazine Derivatives Generated via Click Chemistry,” Australian Journal of Chemistry 69, no. 8 (2016): 905–10.
  • T. El Malah, H.A. Soliman, B.A. Hemdan, R.E. Abdel Mageid, and H.F. Nour, “Synthesis and Antibiofilm Activity of 1,2,3-Triazole-Pyridine Hybrids against Methicillin-Resistant Staphylococcus aureus (MRSA),” New Journal of Chemistry 45, no. 24 (2021): 10822–30.
  • T. El Malah, H.F. Nour, A.A.E. Satti, B.A. Hemdan, and W.A. El-Sayed, “Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers,” Molecules 25, no. 4 (2020): 790.
  • R. Dharavath, N. Nagaraju, M.R. Reddy, D. Ashok, M. Sarasija, M. Vijjulatha, V.T.K. Jyothi, and G. Prashanthi, “Microwave-Assisted Synthesis, Biological Evaluation and Molecular Docking Studies of New Coumarinbased 1,2,3-Triazoles,” RSC Advances 10, no. 20 (2020): 11615–23.
  • H. Khalil, T. El Malah, A.I.A. El Maksoud, I. El Halfawy, A.A. El Rashedy, and M. El Hefnawy, “Identification of Novel and Efficacious Chemical Compounds That Disturb Influenza a Virus Entry in Vitro” Front,” Frontiers in Cellular and Infection Microbiology 7 (2017): 304.
  • A. Rani, G. Singh, A. Singh, U. Maqbool, G. Kaur, and J. Singh, “CuAAC-Ensembled 1,2,3-Triazole-Linked Isosteres as Pharmacophores in Drug Discovery: review,” RSC Advances 10, no. 10 (2020): 5610–35.
  • R. Paul, D. Dutta, R. Paul, and J. Dash, “Target-Directed Azide-Alkyne Cycloaddition for Assembling HIV-1 TAR RNA Binding Ligands,” Angewandte Chemie 59, no. 30 (2020): 12407–11.
  • G. Singh, Diksha, A. Singh, P. Satija, Pawan, Mohit, D. González-Silvera, C. Espinosa-Ruíz, and M.A. Esteban, “Organosilanes and Their Magnetic Nanoparticles as Naked Eye Red Emissive Sensors for Ag + Ions and Potent Anti-Oxidants,” New Journal of Chemistry 45, no. 12 (2021): 5517–25.
  • T. Settypalli, V.R. Chunduri, A.K. Maddineni, N. Begari, R. Allagadda, P. Kotha, and A.R. Chippada, “Design, Synthesis, in Silico Docking Studies and Biological Evaluation of Novel Quinoxalinehydrazide Hydrazone-1,2,3-Triazole Hybrids as α-Glucosidase Inhibitors and Antioxidants,” New Journal of Chemistry 43, no. 38 (2019): 15435–52.
  • L. Han, W. Sheng, X. Li, A. Sik, H. Lin, K. Liu, and L. Wang, “Novel Carbohydrate Modified Berberine Derivatives: Synthesis and in Vitro anti-Diabetic Investigation,” MedChemComm 10, no. 4 (2019): 598–605.
  • S. Iqbal, M.A. Khan, K. Javaid, R. Sadiq, S. Fazal-Ur-Rehman, M.I. Choudhary, and F.Z. Basha, “New Carbazole Linked 1,2,3-Triazoles as Highly Potent Non-Sugar α-Glucosidase Inhibitors,” Bioorganic Chemistry 74 (2017): 72–81.
  • T.E. Malah and H.F. Nour, “Synthesis of Dendronic Triazolo-Pyridazinones and Their Self-Assembly into Nanofibers and Nanorods,” Journal of Nanostructure in Chemistry 8, no. 2 (2018): 159–69.
  • T. El Malah and H.F. Nour, “Click Synthesis of Shape-Persistent Azodendrimers and Their Orthogonal Self-Assembly to Nanofibres,” Australian Journal of Chemistry 71, no. 6 (2018): 463–72.
  • T. El Malah, S. Rolf, S.M. Weidner, A.F. Thünemann, and S. Hecht, “Amphiphilic Folded Dendrimer Discs and Their Thermosensitive Self-Assembly in Water,” Chemistry 18, no. 19 (2012): 5837–42.
  • T. El Malah, A. Ciesielski, L. Piot, S.I. Troyanov, U. Mueller, S. Weidner, P. Samorì, and S. Hecht, “Conformationally Pre-Organized and pH-Responsive Flat Dendrons: Synthesis and Self-Assembly at the Liquid–Solid Interface,” Nanoscale 4, no. 2 (2012): 467–72.
  • D. Zornik, R.M. Meudtner, T. El Malah, C.M. Thiele, and S. Hecht, “Designing Structural Motifs for Clickamers: Exploiting the 1,2,3-Triazole Moiety to Generate Conformationally Restricted Molecular Architectures,” Chemistry 17, no. 5 (2011): 1473–84.
  • A. Cadeddu, A. Ciesielski, T. El Malah, S. Hecht, and P. Samorì, “Modulating the Self-Assembly of Rigid ‘‘Clicked’’ Dendrimers at the Solid–Liquid Interface by Tuning Non-Covalent Interactions between Side Groups,” Chemical Communications 47, no. 38 (2011): 10578–80.
  • L. Piot, R.M. Meudtner, T. El Malah, S. Hecht, and P. Samorì, “Modulating Large-Area Self-Assembly at the Solid–Liquid Interface by pH-Mediated Conformational Switching,” Chemistry 15, no. 19 (2009): 4788–92.
  • M.J. Soltis, H.J. Yeh, K.A. Cole, N. Whittaker, R.P. Wersto, and E.C. Kohn, “Identification and Characterization of Human Metabolites of CAI [5-Amino-1-1(4'-Chlorobenzoyl-3,5-Dichlorobenzyl)-1,2,3-Triazole- 4-Carboxamide)” Drug Metabolism and Disposition 24 (1996): 799–806.
  • C.H.B.P. Devi, K. Vijay, B.H. Babu, S.F. Adil, M.M. Alam, M. Vijjulatha, and M.B. Ansari, “CuSO4/Sodium Ascorbate Catalysed Synthesis of Benzosuberone and 1,2,3-Triazole Conjugates: Design, Synthesis and in Vitro anti-Proliferative Activity,” Journal of Saudi Chemical Society 23, no. 7 (2019): 980–91.
  • D. Dheer, V. Singh, and R. Shankar, “Medicinal Attributes of 1,2,3-Triazoles Current Developments,” Bioorganic Chemistry 71 (2017): 30–54.
  • J.R. Johansson, T. Beke-Somfai, A. Said Stålsmeden, and N. Kann, “Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications,” Chemical Reviews 116, no. 23 (2016): 14726–68.
  • T. Li, E.M. Dief, Z. Kalužná, M. MacGregor, C. Foroutan-Nejad, and N. Darwish, “On-Surface Azide − Alkyne Cycloaddition Reaction: Does It Click with Ruthenium Catalysts?” Langmuir: The ACS Journal of Surfaces and Colloids 38, no. 18 (2022): 5532–41.
  • K. Kacprzak, I. Skiera, M. Piasecka, and Z. Paryzek, “Alkaloids and Isoprenoids Modification by Copper(I)-Catalyzed Huisgen 1,3-Dipolar Cycloaddition (Click Chemistry): Toward New Functions and Molecular Architectures,” Chemical Reviews 116, no. 10 (2016): 5689–743.
  • K. Bozorov, J. Zhao, and H.A. Aisa, “1,2,3-Triazole-Containing Hybrids as Leads in Medicinal Chemistry: A Recent Overview,” Bioorganic & Medicinal Chemistry 27, no. 16 (2019): 3511–31.
  • T. El Malah, M.I. Hegab, H.M. Awad, M.T. Abdel Rahman, F.M.E. Abdel-Megeid, A.H. Shamroukh, R.E. Abdel Mageid, and H.F. Nour, “Benzothiazole-Tethered 1,2,3-Triazoles: Synthesis, Antimicrobial, Antioxidant, and Molecular Docking Studies,” Journal of Molecular Structure 1266 (2022): 133417.
  • T.E. Malah, H. Farag, B.A. Hemdan, R.E. Abdel Mageid, M.T. Abdelrahman, M.A. El-Manawaty, and H.F. Nour, “Synthesis, In Vitro Antimicrobial Evaluation, and Molecular Docking 2 Studies of New Isatin-1,2,3-Triazole Hybrids,” Journal of Molecular Structure 1250 (2022): 131855.
  • M. Lahn, S. Kloeker, and B.S. Berry, “TGF-Beta Inhibitors for the Treatment of Cancer,” Expert Opinion on Investigational Drugs 14, no. 6 (2005): 629–43.
  • S. Mondal, N. Adhikari, S. Banerjee, S.A. Amin, and T. Jha, “Matrix Metalloproteinase-9 (MMP-9) and Its Inhibitors in Cancer: A Minireview,” European Journal of Medicinal Chemistry 194 (2020): 112260.
  • A. Tochowicz, K. Maskos, R. Huber, R. Oltenfreiter, V. Dive, A. Yiotakis, M. Zanda, T. Pourmotabbed, W. Bode, and P. Goettig, “Crystal Structures of MMP-9 Complexes with Five Inhibitors: Contribution of the Flexible Arg424 Side-Chain to Selectivity,” Journal of Molecular Biology 371, no. 4 (2007): 989–1006.
  • H.A. Soliman, A.Y. Mubarak, A. El-Mekabaty, H.M. Awad, and S.S. Elmorsy, “Eco-Friendly Synthesis of Amidochloroalkylnaphthols and Its Related Oxazepinones with Biological Evaluation,” Monatshefte für Chemie – Chemical Monthly 147, no. 4 (2016): 809–16.
  • A. Younis, U. Fathy, A.A. El-Kateb, and H.M. Awad, “Ultrasonic Assisted Synthesis of Novel Anticancer Chalcones Using Water as Green Solvent,” Der Pharma Chemica 8, no. 17 (2016): 129–36.
  • A.F. Kassem, I.F. Nassar, M.T. Abdel-Aal, H.M. Awad, and W.A. El-Sayed, “Synthesis and Anticancer Activity of New ((Furan-2-yl)-1,3,4-Thiadiazolyl)-1,3,4-Oxadiazole Acyclic Sugar Derivatives,” Chemical & Pharmaceutical Bulletin 67, no. 8 (2019): 888–95.
  • E.M. Flefel, W.I. El-Sofany, H.M. Awad, and M. El-Shahat, “First Synthesis for Bis-Spirothiazolidine Derivatives as a Novel Heterocyclic Framework and Their Biological Activity” Mini Rev,” Mini Reviews in Medicinal Chemistry 20, no. 2 (2020): 152–60.
  • A.A.H. Abdel Rahman, I.F. Nassar, A.K.F. Shaban, D.S. EL-Kady, H.M. Awad, and W.A. El Sayed, “Synthesis, Docking Studies into Cdk-2 and Anticancer Activity of New Derivatives Based Pyrimidine Scaffold and Their Derived Glycosides,” Mini Reviews in Medicinal Chemistry 19, no. 13 (2019): 1093–110.
  • A.N. Boshra, H.H.M. Abdu-Allah, A.F. Mohammed, and A.M. Hayallah, “Click Chemistry Synthesis, Biological Evaluation and Docking Study of Some Novel 2′-Hydroxychalcone-Triazole Hybrids as Potent anti-Inflammatory Agents,” Bioorganic Chemistry 95 (2020): 103505.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.