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Research Articles

Synthesis, X-Ray, Spectroscopic Characterization, Hirshfeld Surface Analysis, Molecular Docking, and DFT Calculations of a New Series of 3-Hydrazono and 3-Phenylhydrazono Isatin Derivatives

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Pages 8989-9006 | Received 11 Oct 2022, Accepted 05 Dec 2022, Published online: 09 Jan 2023

References

  • L. El Ghayati, Y. Sert, N. K. Sebbar, Y. Ramli, N. H. Ahabchane, A. Talbaoui, J. T. Mague, B. El Ibrahimi, M. L. Taha, E. M. Essassi, et al., “Syntheses of Novel 1, 5‐Benzodiazepine Derivatives: Crystal Structures, Spectroscopic Characterizations, Hirshfeld Surface Analyses, Molecular Docking Studies, DFT Calculations, Corrosion Inhibition Anticipation, and Antibacterial Activities,” Journal of Heterocyclic Chemistry 58, no. 1 (2021): 270–89. doi:10.1002/jhet.4167
  • S. Hayani, Y. Sert, Y. F. Baba, F. Benhiba, F. O. Chahdi, F.-Z. Laraqui, J. T. Mague, B. El. Ibrahimi, N. K. Sebbar, Y. K. Rodi, et al., “New Alkyl (Cyclohexyl) 2-Oxo-1-(Prop-2-yn-1-yl)-1, 2-Dihydroquinoline-4-Carboxylates: Synthesis, Crystal Structure, Spectroscopic Characterization, Hirshfeld Surface Analysis, Molecular Docking Studies and DFT Calculations,” Journal of Molecular Structure 1227 (2021): 129520. doi:10.1016/j.molstruc.2020.129520
  • P. R. Vijai Anand, K. Suresh Kumar, R. Sivakumar, W. D. Sam Solomon, and K. N. Jayaveera, “Synthesis of Quinazoline Derivatives and Their Biological Activities,” Asian Journal of Chemistry 21, no. 9 (2009): 6656–60.
  • R. R. Kale, V. Prasad, P. P. Mohapatra, and V. K. Tiwari, “Recent Developments in Benzotriazole Methodology for Construction of Pharmacologically Important Heterocyclic Skeletons,” Monatshefte Für Chemie - Chemical Monthly 141, no. 11 (2010): 1159–82. doi:10.1007/s00706-010-0378-1
  • P. Brandão, C. Marques, A. J. Burke, and M. Pineiro, “The Application of Isatin-Based Multicomponent-Reactions in the Quest for New Bioactive and Druglike Molecules,” European Journal of Medicinal Chemistry 211 (2021): 113102. doi:10.1016/j.ejmech.2020.113102
  • V. Sonam and R. Kakkar, “Isatin and Its Derivatives: A Survey of Recent Syntheses, Reactions, and Applications,” Medchemcomm 10, no. 3 (2019): 351–68. doi:10.1039/c8md00585k
  • P. De Matos Cândido-Bacani, M. B. dos Reis, J. M. Serpeloni, T. R. Calvo, W. Vilegas, E. A. Varanda, and I. M. de Syllos Cólus, “Mutagenicity and Genotoxicity of Isatin in Mammalian Cells in Vivo,” Mutation Research 719, no. 12 (2011): 47–51. doi:10.1016/j.mrgentox.2010.11.006
  • S. N. Pandeya, S. Smitha, M. Jyoti, and S. K. Sridhar, “Biological Activities of Isatin and Its Derivatives,” Acta Pharmaceutica (Zagreb, Croatia) 55, no. 1 (2005): 27–46.
  • M. B. Ferrari, C. Pelizzi, G. Pelosi, and M. C. Rodrı́guez-Argüelles, “Preparation, Characterization and X-Ray Structures of 1-Methylisatin 3-Thiosemicarbazone Copper, Nickel and Cobalt Complexes,” Polyhedron 21, no. 2526 (2002): 2593–9. doi:10.1016/S0277-5387(02)01234-2
  • A. Bacchi, M. Carcelli, P. Pelagatti, G. Pelizzi, M. C. Rodriguez-Arguelles, D. Rogolino, C. Solinas, and F. Zani, “Antimicrobial and Mutagenic Properties of Organotin(IV) Complexes with Isatin and N-Alkylisatin Bisthiocarbonohydrazones,” Journal of Inorganic Biochemistry 99, no. 2 (2005): 397–408. doi:10.1016/j.jinorgbio.2004.10.008
  • G. Pelosi, M. Belicchi Ferrari, M. C. Rodríguez-Argüelles, S. Mosquera-Vázquez, and J. Sanmartín, “Sodium 2-Oxo-3-Semicarbazono-2,3-Dihydro-1H-Indole-5-Sulfonate Dihydrate,” Acta Crystallographica Section C: Crystal Structure Communications 62, no. 6 (2006): 241–2.
  • M. C. Rodríuez-Argüelles, M. Belicchi Errari, F. Bisceglie, C. Pelizzi, G. Pelosi, S. Pinelli, and M. Sassi, “Synthesis, Characterization and Biological Activity of Ni, Cu and Zn Complexes of Isatin Hydrazones,” Journal of Inorganic Biochemistry 98, no. 2 (2004): 313–21. doi:10.1016/j.jinorgbio.2003.10.006
  • A. Masunari and L. C. Tavares, “A New Class of Nifuroxazide Analogues: Synthesis of 5-Nitrothiophene Derivatives with Antimicrobial Activity against Multidrug-Resistant Staphylococcus aureus,” Bioorganic & Medicinal Chemistry 15, no. 12 (2007): 4229–36. doi:10.1016/j.bmc.2007.03.068
  • U. Salgın-Gökşen, N. Gökhan-Kelekçi, Ö. Göktaş, Y. Köysal, E. Kılıç, Ş. Işık, G. Aktay, and M. Özalp, “1-Acylthiosemicarbazides, 1,2,4-Triazole-5(4H)-Thiones, 1,3,4-Thiadiazoles and Hydrazones Containing 5-Methyl-2-Benzoxazolinones: Synthesis, Analgesic-anti-Inflammatory and Antimicrobial Activities,” Bioorganic & Medicinal Chemistry 15, no. 17 (2007): 5738–51. doi:10.1016/j.bmc.2007.06.006
  • P. V. Bernhardt, P. C. Sharpe, M. Islam, D. B. Lovejoy, D. S. Kalinowski, and D. R. Richardson, “Iron Chelators of the Dipyridylketone Thiosemicarbazone Class: Precomplexation and Transmetalation Effects on Anticancer Activity,” Journal of Medicinal Chemistry 52, no. 2 (2009): 407–15. doi:10.1021/jm801012z
  • H. Guo, “Isatin Derivatives and Their anti-Bacterial Activities,” European Journal of Medicinal Chemistry 164 (2019): 678–88. doi:10.1016/j.ejmech.2018.12.017
  • A. V. Bogdanov, T. A. Kutuzova, and V. F. Mironov, “First Examples of Isatin Acylhydrazones with Ammonium Fragment,” Russian Journal of General Chemistry 86, no. 3 (2016): 756–7. doi:10.1134/S1070363216030440
  • J. Wang, H. Tan, Y. Li, Y. Ma, Z. Li, and L. W. Guddat, “Chemical Synthesis, in Vitro Acetohydroxyacid Synthase (AHAS) Inhibition, Herbicidal Activity, and Computational Studies of Isatin Derivatives,” Journal of Agricultural and Food Chemistry 59, no. 18 (2011): 9892–900. doi:10.1021/jf2021607
  • X. Zhong, H. L. Wei, W. S. Liu, D. Q. Wang, and X. Wang, “The Crystal Structures of Copper(II), Manganese(II), and Nickel(II) Complexes of a (Z)-2-hydroxy-N′-(2-Oxoindolin-3-Ylidene) Benzohydrazide-Potential Antitumor Agents,” Bioorganic & Medicinal Chemistry Letters 17, no. 13 (2007): 3774–7. doi:10.1016/j.bmcl.2007.04.006
  • B. Malawska, “New Anticonvulsant Agents,” Current Topics in Medicinal Chemistry 5, no. 1 (2005): 69–85. doi:10.2174/1568026053386944
  • S. N. Pandeya, D. Sriram, G. Nath, and E. DeClercq, “Synthesis, Antibacterial, Antifungal and anti-HIV Activities of Schiff and Mannich Bases Derived from Isatin Derivatives and N-[4-(4′-Chlorophenyl) Thiazol-2-yl] Thiosemicarbazide,” European Journal of Pharmaceutical Sciences 9, no. 1 (1999): 25–31. doi:10.1016/S0928-0987(99)00038-X
  • R. S. Varma and W. L. Nobles, “Substituted N-Aminomethylisatins,” Journal of Medicinal Chemistry 10, no. 3 (1967): 510. doi:10.1021/jm00315a060
  • E. M. E. Y. Kharbach, A. Haoudi, Y. Kandri Rodi, M. K. Skalli, and A. Mazzah, “Synthese De Nouveaux Derives De La 5-Bromo-1H-Indole-2,3-Dione a Visee Therapeutique,” Moroccan Journal of Heterocyclic Chemistry 14, no. 1 (2015): 63–8.
  • S. K. Sridhar, M. Saravanan, and A. Ramesh, “Synthesis and Antibacterial Screening of Hydrazones, Schiff and Mannich Bases of Isatin Derivatives,” European Journal of Medicinal Chemistry 36, no. 78 (2001): 615–25. doi:10.1016/S0223-5234(01)01255-7
  • N. Dege, H. Gökce, O. E. Doğan, G. Alpaslan, T. Ağar, S. Muthu, and Y. Sert, “Quantum Computational, Spectroscopic Investigations on N-(2-((2-Chloro-4,5-Dicyanophenyl)Amino)Ethyl)-4-Methylbenzenesulfonamide by DFT/TD-DFT with Different Solvents, Molecular Docking and Drug-Likeness Researches,” Colloids and Surfaces A: Physicochemical and Engineering Aspects 638 (2022): 128311. doi:10.1016/j.colsurfa.2022.128311
  • M. Gümüş, Ş. N. Babacan, Y. Demir, Y. Sert, İ. Koca, and İ. Gülçin, “Discovery of Sulfadrug–Pyrrole Conjugates as Carbonic Anhydrase and Acetylcholinesterase Inhibitors,” Archiv Der Pharmazie 355, no. 1 (2022): 2100242. doi:10.1002/ardp.202100242
  • V. Nayak Badavath, A. Kumar, P. K. Samanta, S. Maji, A. Das, G. Blum, A. Jha, and A. Sen, “Determination of Potential Inhibitors Based on Isatin Derivatives against SARS-CoV-2 Main Protease (Mpro): A Molecular Docking, Molecular Dynamics and Structure-Activity Relationship Studies,” Journal of Biomolecular Structure and Dynamics 40, no. 7 (2022): 3110–28. doi:10.1080/07391102.2020.1845800
  • H. S. Ibrahim, S. M. Abou-Seri, N. S. M. Ismail, M. M. Elaasser, M. H. Aly, and H. A. Abdel-Aziz, “Bis-Isatin Hydrazones with Novel Linkers: Synthesis and Biological Evaluation as Cytotoxic Agents,” European Journal of Medicinal Chemistry 108 (2016): 415–22. doi:10.1016/j.ejmech.2015.11.047
  • Bruker, APEX4, SAINT. (Madison, WI: Bruker AXS LLC, 2021).
  • L. Krause, R. Herbst-Irmer, G. M. Sheldrick, and D. Stalke, “SADABS-2016/2. Bruker AXS Area Detector Scaling and Absorption Correction,” Journal of Applied Crystallography 48, no. Pt 1 (2015): 3–10. doi:10.1107/S1600576714022985
  • G. M. Sheldrick, “Using Phases to Determine the Space Group,” Acta Crystallographica Section A, Foundations and Advances 71, no. Pt 1 (2015): 3–8. doi:10.1107/S2053273314026370
  • G. M. Sheldrick, “Crystal Structure Refinement with SHELXL,” Acta Crystallographica. Section C, Structural Chemistry 71, no. Pt 1 (2015): 3–8. doi:10.1107/S2053229614024218
  • P. R. Spackman, M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, D. Jayatilaka, and M. A. Spackman, “Crystal Explorer: A Program for Hirshfeld Surface Analysis, Visualization and Quantitative Analysis of Molecular Crystals,” Journal of Applied Crystallography 54 (2021): 3.
  • A. D. Becke, “Density‐Functional Thermochemistry. III. The Role of Exact Exchange,” Journal of Chemical Physics. 98, no. 7 (1993): 5648–52. doi:10.1063/1.464913
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Peterson, H. Nakatsuji, et al., Gaussian 16, Revision B.01 (Wallingford, CT: Gaussian, Inc., 2016).
  • R. Dennington, T. Keith, and J. Millam, GaussView, Version 5 (Shawnee Mission, KS: Semichem Inc., 2016).
  • S. Dallakyan and A. J. Olson, “Small-Molecule Library Screening by Docking with PyRx,” Chemical Biology (2014): 243–50.
  • Discovery Studio Visualizer. Dassault Systèmes, San Diego, 2021. http://www.3dsbiovia.com/.
  • F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, “Tables of Bond Lengths Determined by X-Ray and Neutron Diffraction. Part 1. Bond Lengths in Organic Compounds,” Journal of the Chemical Society, Perkin Transactions 2, no. 12 (1987): S1–S18. doi:10.1039/p298700000s1
  • K. Robeyns, T. Rohand, R. Bouhfid, E. M. Essassi, and L. Van Meervelt, “Ethyl 2-(2,3-Dioxoindolin-1-yl)Acetate,” Acta Crystallographica Section E Structure Reports Online 63, no. 4 (2007): o1747–8. doi:10.1107/S1600536807010951
  • K. Mamari, H. Zouihri, E. M. Essassi, and S. W. Ng, “1-Tetradecylindoline-2,3-Dione,” Acta Crystallographica. Section E, Structure Reports Online 66, no. Pt 6 (2010): o1410. doi:10.1107/S1600536810018258
  • F. Z. Qachchachi, Y. Kandri Rodi, A. Haoudi, E. M. Essassi, F. Capet, and H. Zouihri, “IUCRData, 1-(3-Bromopropyl)Indoline-2,3-Dione,” IUCrData 1, no. 4 (2016): x160593. doi:10.1107/S2414314616005939
  • F.-Z. Qachchachi, F. Ouazzani Chahdi, H. Misbahi, M. Bodensteiner, and L. El Ammari, “1-Dodecylindoline-2,3-Dione,” Acta Crystallographica. Section E, Structure Reports Online 70, no. Pt 2 (2014): o229. doi:10.1107/S1600536814001792
  • G. J. Palenik, A. E. Koziol, A. R. Katritzky, and W.-Q. Fan, “Nonbonded Interactions. The Influence of Lone Pair Repulsions on Bond Lengths,” Journal of the Chemical Society, Chemical Communications, no. 9 (1990): 715–6. doi:10.1039/c39900000715
  • I. Rayni, Y. El. Bakri, C.-H. Lai, J. Sebhaoui, E. M. Essassi, and J. T. Mague, “Crystal Structure, DFT Study and Hirshfeld Surface Analysis of 1-Nonyl-2,3-Dihydro-1H-Indole-2,3-Dione,” Acta Crystallographica Section E, Crystallographic Communications 75, no. Pt 8 (2019): 1140–4. doi:10.1107/S2056989019009691
  • I. Rayni, Y. El. Bakri, C.-H. Lai, L. El Ghayati, E. M. Essassi, and J. T. Mague, “Synthesis, Crystal Structure, DFT Calculations and Hirshfeld Surface Analysis of 2-(1-Decyl-2-Oxoindolin-3-Ylidene)Propanedinitrile,” Acta Crystallographica. Section E, Crystallographic Communications 75, no. Pt 1 (2019): 21–5. doi:10.1107/S2056989018017267
  • K. Fukui, “Role of Frontier Orbitals in Chemical Reactions,” Science (New York, N.Y.) 218, no. 4574 (1982): 747–54. doi:10.1126/science.218.4574.747
  • R. G. Parr and R. G. Pearson, “Absolute Hardness: Companion Parameter to Absolute Electronegativity,” Journal of the American Chemical Society 105, no. 26 (1983): 7512–6. doi:10.1021/ja00364a005

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