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Research Articles

Microwave Irradiated Targeted Synthesis of Pyrrolobenzodiazepine Embrace 1,2,3-Triazole by Click Chemistry Synthetic Aspect and Evaluation of Anticancer and Antimicrobial Activity

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Pages 4752-4768 | Received 24 Sep 2020, Accepted 22 Mar 2021, Published online: 22 Apr 2021

References

  • B. K. Ishwar and K. Abhishek , “Synthesis and anti-Inflammatory Activity of Some Novel 1,5 Benzodiazepine Derivatives,” Asian Journal of Pharmaceutical and Clinical Research 9, no. 4 (2016): 63–6.
  • N. O. Terence, A. Redouane, E. G. Mostafa, E. O. Latyfa, E. J. Meryem, C. Laila, C. Yahia, A. Katim, and Z. Amina, “Analgesic and Antioxidant Activities of 4-Phenyl-1,5-Benzodiazepin-2-One and Its Long Carbon Chains Derivatives,” Journal of Chemistry 2019 (2019): 9043570.
  • G. O. Juan and A. K. William, “The Role of Benzodiazepines in the Treatment of Epilepsy,” Current Treatment Options in Neurology 18, no. 18 (2019): 1–11.
  • J. S. David, “The Pharmacology and Mechanisms of Action of New Generation, Non-Benzodiazepine Hypnotic Agents,” CNS Drugs 18, no. 1 (2004): 9–15.
  • W. Leimgruber, V. Stefanović, F. Schenker, A. Karr, and J. Berger, “Isolation and Characterization of Anthramycin, a New Antitumor Antibiotic,” Journal of the American Chemical Society 87, no. 24 (1965): 5791–3.
  • A. Dyeison and E. T. David, “Synthesis of DNA-Interactive Pyrrolo[2,1-c][1,4]Benzodiazepines (PBDs),” Chemical Reviews 111 (2011): 2815–64.
  • H. H. Laurence, R. Teri, E. T. David, R. L. David, G. H. Kenneth, P. H. Robert, R. E. John, G. Gregory Jr., and F. F. Leo, “Pyrrolo[1,4]Benrodiazepine Antitumor Antibiotics: Relationship of DNA Alkylation and Sequence Specificity to the Biological Activity of Natural and Synthetic Compounds,” Chemical Research in Toxicology 1 (1988): 258–68.
  • D. T. Moses and K. Samuel, “Refuin: Non-Cytotoxic Carcinostatic Compound Proliferated by a Thermophilic Actinomycete,” Nature 199 (1963): 501.
  • K. Ahmed, G. Ramakrishna, V. L. Nayak, P. Raju, A. V. Subba Rao, A. Viswanath, M. V. Vishnuvardhan, R. Sistla, and G. Srinivas, “Design and Synthesis of Benzo[c,d]Indolone-Pyrrolobenzodiazepine Conjugates as Potential Anticancer Agents,” Bioorganic & Medicinal Chemistry 20, no. 2 (2012): 789–800.
  • A. H. John and H. Daniel, “Small Molecule Drugs – Optimizing DNA Damaging Agent-Based Therapeutics,” Current Opinion in Pharmacology 12 (2012): 398–402.
  • A. M. Burger, P. M. Loadman, D. E. Thurston, R. Schultz, H. H. Fiebig, and M. C. Bibby, “Preclinical Pharmacology of the Pyrrolobenzodiazepine (PBD) Monomer DRH-417 (NSC 709119),” Journal of Chemotherapy 19, no. 1 (2007): 66–78.
  • A. H. John, “The Development of Pyrrolobenzodiazepines as Antitumour Agents,” Expert Opinion on Investigational Drugs 20 (2011): 733–44.
  • P. H. Robert, M. H. Sidney, L. R. Vincent, J. M. Ian, and H. H. Laurence, “DNA Sequence Specificity of the Pyrrolo [1,4]Benzodiazepine Antitumor Antibiotics. Methidiumpropyl-EDTA-Iron(11) Footprinting Analysis of DNA Binding Sites for Anthramycin and Related Drugs,” Biochemistry 25 (1986): 1249–58.
  • J. Wei, J. Chen, J. Xu, L. Cao, H. Deng, W. Sheng, H. Zhang, and W. Cao, “Solution-Phase Perfluoroalkylation of C60 Leads to Efficient and Selective Synthesis of Bis-Perfluoroalkylated Fullerenes,” Journal of Fluorine Chemistry 133 (2012): 146–54.
  • L. Liang and D. Astruc, “The Copper(I)-Catalyzed Alkyne-Azide Cycloaddition (CuAAC) “Click” Reaction and Its Applications,” Coordination Chemistry Reviews 255, no. 23–24 (2011): 2933–45.
  • M. Meldal, “Polymer ‘‘Clicking’’ by CuAAC Reactions,” Macromolecular Rapid Communications 29, no. 12–13 (2008): 1016–51.
  • V. D. Bock, H. Hiemstra, and J. H. van Maarseveen, “CuI -Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective,” European Journal of Organic Chemistry 2006, no. 1 (2006): 51–68.
  • M. Meldal and C. W. Tornøe, “Cu-Catalyzed Azide-Alkyne Cycloaddition,” Chemical Reviews 108, no. 8 (2008): 2952–3015.
  • J. E. Hein and V. V. Fokin, “Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) and Beyond: New Reactivity of Copper(I) Acetylides,” Chemical Society Reviews 39, no. 4 (2010): 1302–15. [20309487]
  • J. E. Moses and A. D. Moorhouse, “The Growing Applications of Click Chemistry,” Chemical Society Reviews 36, no. 8 (2007): 1249–62.
  • X. L. Wang, K. Wan, and C. H. Zhou, “Synthesis of Novel Sulfanilamide-Derived 1,2,3-Triazoles and Their Evaluation for Antibacterial and Antifungal Activities,” European Journal of Medicinal Chemistry 45, no. 10 (2010): 4631–9.
  • D. Dheer, V. Singh, and R. Shankar, “Medicinal Attributes of 1,2,3-Triazoles: Current Developments,” Bioorganic Chemistry 71 (2017): 30–54.
  • P. H. Olesen, A. R. Sorensen, B. Urso, P. Kurtzhals, A. N. Bowler, U. Ehrbar, and B. F. Hansen, “Synthesis and In Vitro Characterization of 1-(4-Aminofurazan-3-yl)-5-Dialkylaminomethyl-1H-[1,2,3]Triazole-4-Carboxylic Acid Derivatives. A New Class of Selective GSK-3 Inhibitors,” Journal of Medicinal Chemistry 46, no. 15 (2003): 3333–41.
  • E. K. Moltzen, H. Pedersen, K. P. Bogeso, E. Meier, K. Frederiksen, C. Sanchez, and K. L. Lembol, “Bioisosteres of Arecoline: 1,2,3,6-Tetrahydro-5-pyridyl-Substituted and 3-Piperidyl-Substituted Derivatives of Tetrazoles and 1,2,3-Triazoles. Synthesis and Muscarinic Activity,” Journal of Medicinal Chemistry 37, no. 24 (1994): 4085–99.
  • A. Giraudo, J. Krall, B. Nielsen, T. E. Sorensen, K. T. Kongstad, B. Rolando, D. Boschi, B. Frolund, and M. L. Lolli, “4-Hydroxy-1,2,3-Triazole Moiety as Bioisostere of the Carboxylic Acid Function: A Novel Scaffold to Probe the Orthosteric γ-Aminobutyric Acid Receptor Binding Site,” European Journal of Medicinal Chemistry 158 (2018): 311–21.
  • R. W. Carling, K. W. Moore, L. J. Street, D. Wild, C. Isted, P. D. Leeson, S. Thomos, D. O’Connor, R. M. Mckernan, K. Quirk, et al. “3-Phenyl-6-(2-Pyridyl)Methyloxy-1,2,4-Triazolo[3,4-a]Phthalazines and Analogues: High-Affinity Gamma-Aminobutyric acid-A Benzodiazepine Receptor Ligands with Alpha 2, Alpha 3, and Alpha 5-Subtype Binding Selectivity over Alpha 1,” Journal of Medicinal Chemistry 47 (2004): 1087–822.
  • S. D. Hadiyal, N. D. Parmar, P. L. Kalavadiya, J. N. Lalpara, and H. S. Joshi, “Microwave-Assisted Three-Component Domino Synthesis of Polysubstituted 4H-Pyran Derivatives and Their Anticancer Activity,” Russian Journal of Organic Chemistry 56, no. 4 (2020): 671–8.
  • N. D. Parmar, S. D. Hadiyal, V. H. Kapupara, and H. S. Joshi, “Microwave-Assisted Synthesis of (2-Butyl-5-Nitrobenzo[b]Furan-3-yl)-[4-(Substituted Ethynyl)Phenyl] Methanones,” Arkivoc 2018, no. 7 (2018): 143–53.
  • M. R. Boyd and K. D. Paull, “Some Practical Considerations and Applications of the National Cancer Institute In Vitro Anticancer Drug Discovery Screen,” Drug Development Research 34, no. 2 (1995): 91–109.
  • K. D. Paull, R. H. Shoemaker, L. Hodes, A. Monks, D. A. Scudiero, L. Rubinstein, J. Plowman, and M. R. Boyd, “Display and Analysis of Patterns of Differential Activity of Drugs against Human Tumor Cell Lines: Development of Mean Graph and COMPARE Algorithm,” Journal of the National Cancer Institute 81, no. 14 (1989): 1088–92.
  • M. Anne, S. Dominic Philip, S. Robert, S. Kenneth, V. David, H. Curtis, L. John, C. Paul, V. W. Anne, G. G. Marcia, et al. “Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines,” Journal of the National Cancer Institute 83 (1991): 757–66.
  • C. M. Mann and J. L. Markham, “A New Method for Determining the Minimum Inhibitory Concentration of Essential Oils,” Journal of Applied Microbiology 84, no. 4 (1998): 538–44.
  • T. E. A. Du and M. Rautenbach, “A Sensitive Standardised Micro-Gel Well Diffusion Assay for the Determination of Antimicrobial Activity,” Journal of Microbiological Methods 42, no. 2 (2000): 159–65.
  • C. Valgas, S. M. De Souza, E. F. A. Smânia, and A. Smânia, “Screening Methods to Determine Antibacterial Activity of Natural Products,” Brazilian Journal of Microbiology 38, no. 2 (2007): 369–80.

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