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Research Articles

Synthesis, X-Ray Structural Analysis and Computational Studies of a Novel Bis(2-Thienyl)Disulfide Derivative

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Pages 2852-2860 | Received 25 Jun 2020, Accepted 09 Nov 2020, Published online: 30 Nov 2020

References

  • J. A. Joule and K. Mills, Heterocyclic Chemistry, 4th ed. (Oxford: Blackwell, 2000).
  • A. P. Taylor, R. P. Robinson, Y. M. Fobian, D. C. Blakemore, L. H. Jones, and O. Fadeyi, “Modern Advances in Heterocyclic Chemistry in Drug Discovery,” Organic & Biomolecular Chemistry 14, no. 28 (2016): 6611–37.
  • G. Brahmachari, Green Synthetic Approaches for Biologically Relevant Heterocycles (Netherlands: Elsevier, 2014).
  • A. C. Flick, C. A. Leverett, H. X. Ding, E. McInturff, S. J. Fink, C. J. Helal, and C. J. O'Donnell, “Synthetic Approaches to the New Drugs Approved during 2017,” Journal of Medicinal Chemistry 62, no. 16 (2019): 7340–82.
  • R. Shah, and P. K. Verma, “Therapeutic Importance of Synthetic Thiophene,” Chemistry Central Journal 12, no. 1 (2018): 137.
  • Y. N. Mabkhot, F. Alatibi, N. N. E. El-Sayed, S. Al-Showiman, N. A. Kheder, A. Wadood, A. Rauf, S. Bawazeer, and T. B. Hadda, “Antimicrobial Activity of Some Novel Armed Thiophene Derivatives and Petra/Osiris/Molinspiration (POM) Analyses,” Molecules 21, no. 2 (2016): 222.
  • A. M. Khalil, M. A. Berghot, and M. A. Gouda, “Synthesis and Antibacterial Activity of Some New Thiazole and Thiophene derivatives,” Eur J Med Chem44, no. 11 (2009): 4434–40.
  • M. Z. Elsabee, E. A. Ali, S. M. Mokhtar, and M. Eweis, “Synthesis, Characterization Polymerization and Antibacterial Properties of Novel Thiophene Substituted Acrylamide,” Reactive and Functional Polymers 71, no. 12 (2011): 1187–94.
  • M. K. Parai, G. Panda, V. Chaturvedi, Y. K. Manju, and S. Sinha, “Thiophene Containing Triarylmethanes as Antitubercular Agents,” Bioorganic & Medicinal Chemistry Letters 18, no. 1 (2008): 289–92.
  • L. Pulipati, P. Yogeeswari, D. Sriram, and S. Kantevari, “Click-Based Synthesis and Antitubercular Evaluation of Novel Dibenzo[b,d]Thiophene-1,2,3-Triazoles with Piperidine, Piperazine, Morpholine and Thiomorpholine Appendages,” Bioorganic & Medicinal Chemistry Letters 26, no. 11 (2016): 2649–54.
  • J. B. Hudson, E. A. Graham, N. Miki, G. H. N. Towers, L. L. Hudson, R. Rossi, A. Carpita, and D. Neri, “Photoactive Antiviral and Cytotoxic Activities of Synthetic Thiophenes and Their Acetylenic Derivatives,” Chemosphere 19, no. 8–9 (1989): 1329–43.
  • C. Mugnaini, A. Rabbito, A. Brizzi, N. Palombi, S. Petrosino, R. Verde, V. Di. Marzo, A. Ligresti, and F. Corelli, “Synthesis of Novel 2-(1-Adamantanylcarboxamido)Thiophene Derivatives. Selective Cannabinoid Type 2 (CB2) Receptor Agonists as Potential Agents for the Treatment of Skin Inflammatory Disease,” European Journal of Medicinal Chemistry 161, (2019): 239–51.
  • L. John, A. Dasan, R. S. Joseyphus, and I. H. Joe, “Molecular Docking, Structural Characterization, DFT and Cytotoxicity Studies of Metal(II) Schiff Base Complexes Derived from Thiophene-2-Carboxaldehyde and l-Histidine,” Journal of Molecular Structure 1198, (2019): 126934.
  • R. J. Cremlyn, An Introduction to Organosulfur Chemistry (New York: Wiley & Sons, 1996).
  • J. M. Fletcher, and R. A. Hughes, “A Novel Approach to the Regioselective Synthesis of a Disulfide-Linked Heterodimeric Bicyclic Peptide Mimetic of Brain-Derived Neurotrophic Factor,” Tetrahedron Letters 45, no. 38 (2004): 6999–7001.
  • Vivekananda M. Vrudhula, John F. MacMaster, Zhengong Li, David E. Kerr, and Peter D. Senter, “Reductively Activated Disulfide Prodrugs of Paclitaxel,” Bioorganic & Medicinal Chemistry Letters 12, no. 24 (2002): 3591–4.
  • Béatrice Roy, Stéphane Chambert, Michel Lepoivre, Anne-Marie Aubertin, Jan Balzarini, and Jean-Luc Décout, “Deoxyribonucleoside 2'- or 3'-Mixed Disulfides: Prodrugs to Target Ribonucleotide Reductase and/or to Inhibit HIV Reverse Transcription,” Journal of Medicinal Chemistry 46, no. 13 (2003): 2565–8.
  • Y. Mu, M. Nodwell, J. L. Pace, J. P. Shaw, and J. K. Judice, “Vancomycin Disulfide Derivatives as Antibacterial Agents,” Bioorganic & Medicinal Chemistry Letters 14, no. 3 (2004): 735–8.
  • Y. N. Mabkhot, J. M. A. Khaled, M. A. S. Sultan, N. S. H. Alharbi, S. S. Al-Showiman, H. A. Ghabbour, A. Alsayari, A. B. Muhsinah, and H. Algarni, “The Novel Economical Synthesis and Antimicrobial Activity of a Trithiocarbonate Derivative,” Bioorganic Chemistry 91, (2019): 103157
  • N. I. Astrakhantseva, V. G. Zhiryakov, and P. I. Abramenko, “Synthesis of 2-Mercapto-Substituted Thieno[2,3-d]Thiazoles and Benzothieno[3,2-d] Thiazoles,” Chemistry of Heterocyclic Compounds 12, no. 10 (1976): 1123–4.
  • K. Clarke, W. R. Fox, and R. M. Scrowston, “Condensed Isothiazoles. Part 5. Thieno[2,3-d]Isothiazoles and Thieno[3,2-d]Isothiazoles,” Journal of the Chemical Society, Perkin Transactions 1, (1980): 1029–37.
  • G. Capozzi, G. Modena, in The Chemistry of the Thiol Group, edited by S. Patai part 2, ch. 17, p. 801 (London: John & Sons, 1974), and references cited therein.
  • (a) A. A. Oswald and T. J. Wallance, in Organic Sulfur Compounds, edited by N. Kharash vol. 2, ch. 8 (New York: Pergamon Press, 1964).; (b) T. J. Wallance, A. Schriesheim, and W. Bartok, "The Base-catalyzed Oxidation of Mercaptans. III. Role of the Solvent and Effect of Mercaptan Structure on the Rate Determining Step1,2,” The Journal of Organic Chemistry 28 (1963): 1311–1314; (c) T. J. Wallance and A. Schriesheim, “Solvent Effects in the Base-Catalyzed Oxidation of Mercaptans with Molecular Oxygen,” The Journal of Organic Chemistry 27 (1962): 1514–1516.
  • C. Oefner, M. Bandera, A. Haldimann, H. Laue, H. Schulz, S. Mukhija, S. Parisi, L. Weiss, S. Lociuro, and G. E. Dale, “Increased Hydrophobic Interactions of Iclaprim with Staphylococcus aureus Dihydrofolate Reductase are Responsible for the Increase in Affinity and Antibacterial activity,” Journal of Antimicrobial Chemotherapy 63, no. 4 (2009): 687–98.
  • M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, P. R. Spackman, D. Jayatilaka, and M. A. Spackman, Crystal Explorer 17, (2017). University of Western Australia. http://hirshfeldsurface.net.
  • (a) M. J. Frisch, G.W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, GAUSSIAN 09. Revision A02. Wallingford CT: Gaussian Inc., 2009), and (b) T. Keith, J. Millam, GaussView, Version 4.1, R. Dennington II (Shawnee Mission, KS: Semichem Inc., 2007).
  • B. Marten, K. Kim, C. Cortis, R. A. Friesner, R. B. Murphy, M. N. Ringnalda, D. Sitkoff, and B. Honig, “New Model for Calculation of Solvation Free Energies: Correction of Self-Consistent Reaction Field Continuum Dielectric Theory for Short-Range Hydrogen-Bonding Effects,” The Journal of Physical Chemistry 100, no. 28 (1996): 11775–88.
  • D. J. Tannor, B. Marten, R. Murphy, R. A. Friesner, D. Sitkoff, A. Nicholls, M. Ringnalda, W. A. Goddard, and B. Honig, “Accurate First Principles Calculation of Molecular Charge Distributions and Solvation Energies from Ab Initio Quantum Mechanics and Continuum Dielectric Theory,” Journal of the American Chemical Society 116, no. 26 (1994): 11875–82.
  • R. Ditchfield, “Self-Consistent Perturbation Theory of Diamagnetism. I. A Gauge-Invariant LCAO Method for N.M.R. chemical Shifts,” Molecular Physics 27, no. 4 (1974): 789–807.
  • Krzysztof Wolinski, James F. Hinton, and Peter Pulay, “Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations,” Journal of the American Chemical Society 112, no. 23 (1990): 8251–60.
  • P. Labra-Vázquez, A. Galano, M. Romero-Ávila, M. Flores-Álamo, and M. A. Iglesias-Arteaga, “Unambiguous Assignment of 13C NMR Signals in Epimeric 4,5-epoxy3-Oxo-Steroids Assisted by X-Ray Diffraction and Gauge Invariant Atomic Orbitals Calculation of Absolute Isotropic Shieldings,”Arkivoc 2013, no. 4 (2013): 107–25.
  • P. Labra-Vázquez, A. Lugo-Aranda, M. Maldonado, R. Arcos-Ramos, M. Carreon-Castro, R. Santillan, and N. Farfán, “On the Molecular Structure of (E)-3-(9H-Fluoren-2-yl)-1-(Pyridin-2-yl)Prop-2-en-1-One,Theoretical Calculations and SXRD Studies,” Journal of Molecular Structure 1101, (2015): 116–23.
  • M. E. Ochoa, P. Labra-Vázquez, N. Farfán, and R. Santillan, “Designed Synthesis and Crystallization of Isomorphic Molecular Gyroscopes with Cell-like Bilayer Self-Assemblies,” Crystal Growth & Design 18, no. 5 (2018): 2795–803.
  • E. D. Glendening, A. E. Reed, J. E. Carpenter, and F. Weinhold, NBO Version 3.1 (Madison, WI: University of Wisconsin, 1998).
  • G. Sheldrick, “A Short History of ShelX,” Acta Crystallographica. Section A, Foundations of Crystallography 64, no. Pt 1 (2008): 112–22.
  • Sheldrick, G. M. SHELXTL-PC (Version 5.1) (Madison, WI: Siemens Analytical Instruments, Inc., 1997).

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