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Research Articles

Ambroxol: Insight into the Crystal Structure, Hirshfeld Surface Analysis and Computational Study

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Pages 2599-2617 | Received 10 Nov 2021, Accepted 25 Feb 2022, Published online: 14 Mar 2022

References

  • János Fischer and C. Robin Ganellin, Analogue-Based Drug Discovery (Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA, 2006), 544.
  • “Coronavirus disease (COVID-19),” World Health Organization, last modified November 3, 2021, https://www.who.int/health-topics/coronavirus#tab=tab_1 (accessed November 10, 2021).
  • “WHO Director-General's opening remarks at the media briefing on COVID-19 - 11 March 2020,” World Health Organization, last modified March 11, 2020, https://www.who.int/dg/speeches/detail/who-director-general-s-opening-remarks-at-the-media-briefing-on-covid-19–-11-march-2020 (accessed November 10, 2021).
  • “WHO Coronavirus (COVID-19) Dashboard,” World Health Organization, last modified November 10, 2021, https://covid19.who.int/ (accessed November 10, 2021).
  • “COVID-19 vaccines,” World Health Organization, last modified November 3, 2021, https://www.who.int/emergencies/diseases/novel-coronavirus-2019/covid-19-vaccines (accessed November 10, 2021).
  • Myasar Alkotaji, “Azithromycin and Ambroxol as Potential Pharmacotherapy for SARS-CoV-2,” International Journal of Antimicrobial Agents 56, no. 6 (2020): 106192. doi:10.1016/j.ijantimicag.2020.106192.
  • Burak Ay, Onur Şahin, Burcu Saygıdeğer Demir, Yasemin Saygideger, José M. López-de-Luzuriaga, Ghodrat Mahmoudi, and Damir A. Safin, “Antitumor Effects of Novel Nickel–Hydrazone Complexes in Lung Cancer Cells,” New Journal of Chemistry 44, no. 21 (2020): 9064–72. doi:10.1039/D0NJ00921K.
  • Burcu Saygıdeğer Demir, Ghodrat Mahmoudi, Aycan Sezan, Ezgi Derinöz, Eylem Nas, Yasemin Saygideger, Fedor I. Zubkov, Ennio Zangrando, and Damir A. Safin, “Evaluation of the Antitumor Activity of a Series of the Pincer-Type Metallocomplexes Produced from Isonicotinohydrazide Derivative,” Journal of Inorganic Biochemistry 223 (2021): 111525. doi:10.1016/j.jinorgbio.2021.111525.
  • Alexey A. Shiryaev, Anastasiya N. Goncharenko, Tatyana M. Burkhanova, Larisa E. Alkhimova, Maria G. Babashkina, Ravikumar Chandrasekaran, and Damir A. Safin, “A Chiral (1R,2R)-N,N′-Bis-(Salicylidene)-1,2-Diphenyl-1,2-Ethanediamine Schiff Base Dye: synthesis, Crystal Structure, Hirshfeld Surface Analysis, Computational Study, Photophysical Properties and in Silico Antifungal Activity,” Journal of the Iranian Chemical Society 18, no. 11 (2021): 2897–911. doi:10.1007/s13738-021-02237-5.
  • Maria G. Babashkina, Antonio Frontera, Alexander V. Kertman, Yasemin Saygideger, Swaminathan Murugavel, and Damir A. Safin, “Favipiravir: insight into the Crystal Structure, Hirshfeld Surface Analysis and Computational Study,” Journal of the Iranian Chemical Society 19, no. 1 (2022): 85–94. doi:10.1007/s13738-021-02285-x.
  • Larisa E. Alkhimova, Maria G. Babashkina, and Damir A. Safin, “Computational Analysis of Aspirin,” Journal of Molecular Structure 1251 (2022): 131975. doi:10.1016/j.molstruc.2021.131975.
  • Artem V. Sharov, Tatyana M. Burkhanova, Tugba Taskin-Tok, Maria G. Babashkina, and Damir A. Safin, “Computational Analysis of Molnupiravir,” International Journal of Molecular Sciences 23, no. 3 (2022): 1508. doi:10.3390/ijms23031508.
  • Tatyana M. Burkhanova, Maria G. Babashkina, Tugba Taskin-Tok, Artem V. Sharov, and Damir A. Safin, “Naphthalene-Based bis-N-Salicylidene Aniline Dyes: Crystal Structures, Hirshfeld Surface Analysis, Computational Study and Molecular Docking with the SARS-CoV-2,” Journal of the Iranian Chemical Society (2021). doi:10.1007/s13738-021-02438-y.
  • Colin R. Groom, Ian J. Bruno, Matthew P. Lightfoot, and Suzanna C. Ward, “The Cambridge Structural Database,” Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials 72, no. Pt 2 (2016): 171–9. doi:10.1107/S2052520616003954.
  • M. R. Caira, A. Foppoli, M. E. Sangalli, L. Zema, and F. Giordano, “Thermal and Structural Properties of Ambroxol Polymorphs,” Journal of Thermal Analysis and Calorimetry 77, no. 2 (2004): 653–62. doi:10.1023/B:JTAN.0000039001.05945.42.
  • Mark A. Spackman and Dylan Jayatilaka, “Hirshfeld Surface Analysis,” CrystEngComm 11, no. 1 (2009): 19–32. doi:10.1039/B818330A.
  • Mark A. Spackman, and Joshua J. McKinnon, “Fingerprinting Intermolecular Interactions in Molecular Crystals,” CrystEngComm 4, no. 66 (2002): 378–92. doi:10.1039/B203191B.
  • Peter R. Spackman, Michael J. Turner, Joshua J. McKinnon, Stephen K. Wolff, Daniel J. Grimwood, Dylan Jayatilaka, and Mark A. Spackman, “CrystalExplorer: A Program for Hirshfeld Surface Analysis, Visualization and Quantitative Analysis of Molecular Crystals,” Journal of Applied Crystallography 54, no. Pt 3 (2021): 1006–11. doi:10.1107/S1600576721002910.
  • Christian Jelsch, Krzysztof Ejsmont, and Loic Huder, “The Enrichment Ratio of Atomic Contacts in Crystals, an Indicator Derived from the Hirshfeld Surface Analysis,” IUCrJ 1, no. Pt 2 (2014): 119–28. doi:10.1107/S2052252514003327.
  • Roy Dennington, Todd A. Keith, and John M. Millam, GaussView Version 6.0 (Shawnee Mission, KS: Semichem Inc., 2016).
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. and D. J. Fox. 2013. Gaussian 09, Revision D.01.
  • R. Krishnan, J. S. Binkley, R. Seeger, and J. A. Pople, “Self‐Consistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions,” The Journal of Chemical Physics 72, no. 1 (1980): 650–4. doi:10.1063/1.438955.
  • Axel D. Becke, “Density‐Functional Thermochemistry. III. The Role of Exact Exchange,” The Journal of Chemical Physics 98, no. 7 (1993): 5648–52. doi:10.1063/1.464913.
  • Michael J. Frisch, John A. Pople, and J. Stephen Binkley, “Self‐Consistent Molecular Orbital Methods 25. Supplementary Functions for Gaussian Basis Sets,” The Journal of Chemical Physics 80, no. 7 (1984): 3265–9. doi:10.1063/1.447079.
  • Michal H. Jamroz, “Vibrational Energy Distribution Analysis (VEDA): Scopes and Limitations,” Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 114 (2013): 220–30.
  • Oleg Trott and Arthur J. Olson, “AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading,” Journal of Computational Chemistry 31, no. 2 (2010): 455–61. doi:10.1002/jcc.21334.
  • Helen M. Berman, John Westbrook, Zukang Feng, Gary Gilliland, T. N. Bhat, Helge Weissig, Ilya N. Shindyalov, and Philip E. Bourne, “The Protein Data Bank,” Nucleic Acids Research 28, no. 1 (2000): 235–42. doi:10.1093/nar/28.1.235.
  • BIOVIA Discovery Studio, (San Diego: Dassault Systèmes, 2020).
  • Garrett M. Morris, Ruth Huey, William Lindstrom, Michel F. Sanner, Richard K. Belew, David S. Goodsell, and Arthur J. Olson, “AutoDock4 and AutoDockTools4: Automated Docking with Selective Receptor Flexibility,” Journal of Computational Chemistry 30, no. 16 (2009): 2785–91. doi:10.1002/jcc.21256.
  • P. Geerlings, F. De Proft, and W. Langenaeker, “Conceptual Density Functional Theory,” Chemical Reviews 103, no. 5 (2003): 1793–874. doi:10.1021/cr990029p.
  • Can Alaşalvar, Nuri Öztürk, Alaa A.-M. Abdel-Aziz, Halil Gökçe, Adel S. El-Azab, Manal A. El-Gendy, and Yusuf Sert, “Molecular Structure, Hirshfeld Surface Analysis, Spectroscopic (FT-IR, Laser-Raman, UV–Vis. and NMR), HOMO-LUMO and NBO Investigations on N-(12-Amino-9,10-Dihydro-9,10-Ethanoanthracen-11-yl)-4-Methylbenzenesulfonamide,” Journal of Molecular Structure 1171 (2018): 696–705. doi:10.1016/j.molstruc.2018.06.038.
  • Yusuf Sert, Mehmet Gümüş, Halil Gökçe, İbrahim Kani, and İrfan Koca, “Molecular Docking, Hirshfeld Surface, Structural, Spectroscopic, Electronic, NLO and Thermodynamic Analyses on Novel Hybrid Compounds Containing Pyrazole and Coumarin Cores,” Journal of Molecular Structure 1171 (2018): 850–66. doi:10.1016/j.molstruc.2018.06.069.
  • Dhaybia Douche, Yusuf Sert, Silvia A. Brandán, Ameed A. Kawther, Bayram Bilmez, Necmi Dege, Ahmed El Louzi, Khalid Bougrin, Khalid Karrouchi, and Banacer Himmi, “5-((1H-Imidazol-1-yl)Methyl)Quinolin-8-ol as Potential Antiviral SARS-CoV-2 Candidate: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT and Molecular Docking Studies,” Journal of Molecular Structure 1232 (2021): 130005. doi:10.1016/j.molstruc.2021.130005.
  • İrfan Çapan, Mehmet Gümüş, Halil Gökce, Hidayet Çetin, Yusuf Sert, and İrfan Koca, “Synthesis, Dielectric Properties, Molecular Docking and ADME Studies of Pyrrole-3-Ones,” Journal of Biomolecular Structure and Dynamics (2021): 1–17. doi:10.1080/07391102.2021.1914174.

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