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Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT, and DNA-Binding Studies of (E)-2-(3-Hydroxy-4-Methoxybenzylidene)Hydrazinecarbothioamide

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Abstract

(E)-2-(3-Hydroxy-4-methoxybenzylidene)hydrazinecarbothioamide 3 was synthesized by reacting thiosemicarbazide with 2-hydorxy-3-methoxybenzaldehyde in dry ethanol. The structure was elucidated by spectroscopic (FT-IR, 1H NMR, and 13C NMR) and single crystal X-ray diffraction techniques. A detailed analysis of the intermolecular interactions has been performed based on the Hirshfeld surfaces and their associated two-dimensional fingerprint plots. DFT, spectroscopic, and electrochemical DNA-binding analysis confirmed that the compound is reactive to bind with DNA. Viscometric studies suggested that compound 3 has a mixed mode of interaction and intercalated into the DNA base pairs predominantly along with the possibility of electrostatic interactions.

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References

  1. Qin, W., Long, S., Panunzio, M., & Biondi, S. (2013). Schiff bases: a short survey on an evergreen chemistry tool. Molecules, 18(10), 12264–12289.

    Article  CAS  Google Scholar 

  2. Yoon, T. P., & Jacobsen, E. N. (2003). Privileged chiral catalysts. Science, 299(5613), 1691–1693.

    Article  CAS  Google Scholar 

  3. Whiteoak, C. J., Salassa, G., & Kleij, A. W. (2012). Recent advances with π-conjugated salen systems. Chemical Society Reviews, 41(2), 622–631.

    Article  CAS  Google Scholar 

  4. Szumna, A. (2010). Inherently chiral concave molecules—from synthesis to applications. Chemical Society Reviews, 39(11), 4274–4285.

    Article  CAS  Google Scholar 

  5. Frischmann, P. D., & MacLachlan, M. J. (2013). Metallocavitands: an emerging class of functional multimetallic host molecules. Chemical Society Reviews, 42(3), 871–890.

    Article  CAS  Google Scholar 

  6. Gupta, L. K., & Sutar, A. K. (2008). Catalytic activities of Schiff base transition metal complexes. Coordination Chemistry Reviews, 252(12–14), 1420–1450.

    Article  CAS  Google Scholar 

  7. Zhang, J., Xu, L., & Wong, W. Y. (2018). Energy materials based on metal Schiff base complexes. Coordination Chemistry Reviews, 355, 180–198.

    Article  CAS  Google Scholar 

  8. Khuhawar, M. Y., Mughal, M. A., & Channar, A. H. (2004). Synthesis and characterization of some new Schiff base polymers. European Polymer Journal, 40(4), 805–809.

    Article  CAS  Google Scholar 

  9. Sánchez, C. O., Bèrnede, J. C., Cattin, L., Makha, M., & Gatica, N. (2014). Schiff base polymer based on triphenylamine moieties in the main chain. Characterization and studies in solar cells. Thin Solid Films, 562, 495–500.

    Article  Google Scholar 

  10. Foo, K. L., Ha, S. T., Lin, C. M., Lin, H. C., Lee, S. L., Yeap, G. Y., & Sastry, S. S. (2015). Synthesis, characterization and mesomorphic properties of new symmetrical dimer liquid crystals derived from benzothiazole. Karbala International Journal of Modern Science, 1(3), 152–158.

    Article  Google Scholar 

  11. Ha, S. T., Koh, T. M., Lee, S. L., Yeap, G. Y., Lin, H. C., & Ong, S. T. (2010). Synthesis of new Schiff base ester liquid crystals with a benzothiazole core. Liquid Crystals, 37(5), 547–554.

    Article  CAS  Google Scholar 

  12. Jia, Y., & Li, J. (2014). Molecular assembly of Schiff base interactions: construction and application. Chemical Reviews, 115(3), 1597–1621.

    Article  Google Scholar 

  13. Kajal, A., Bala, S., Kamboj, S., Sharma, N., & Saini, V. (2013). Schiff bases: a versatile pharmacophore. Journal of Catalysts, 2013, 1–14.

    Article  Google Scholar 

  14. Hameed, A., al-Rashida, M., Uroos, M., Abid Ali, S., & Khan, K. M. (2017). Schiff bases in medicinal chemistry: a patent review (2010-2015). Expert Opinion on Therapeutic Patents, 27(1), 63–79.

    Article  CAS  Google Scholar 

  15. Desai, S. Β., Desai, P. B., & Desai, K. R. (2001). Synthesis of some Schiff bases, thiazolidinones and azetidinones derived from 2, 6-diaminobenzo [1, 2-d: 4, 5-d'] bisthiazole and their anticancer activities. Heterocyclic Communications, 7(1), 83–90.

    Article  CAS  Google Scholar 

  16. Przybylski, P., Huczynski, A., Pyta, K., Brzezinski, B., & Bartl, F. (2009). Biological properties of Schiff bases and azo derivatives of phenols. Current Organic Chemistry, 13(2), 124–148.

    Article  CAS  Google Scholar 

  17. Aziz, A. A. A., Salem, A. N. M., Sayed, M. A., & Aboaly, M. M. (2012). Synthesis, structural characterization, thermal studies, catalytic efficiency and antimicrobial activity of some M (II) complexes with ONO tridentate Schiff base N-salicylidene-o-aminophenol (saphH2). Journal of Molecular Structure, 1010, 130–138.

    Article  Google Scholar 

  18. Sokmen, B. B., Gumrukcuoglu, N., Ugras, S., Sahin, H., Sagkal, Y., & Ugras, H. I. (2015). Synthesis, antibacterial, antiurease, and antioxidant activities of some new 1,2,4-triazole Schiff base and amine derivatives. Applied Biochemistry and Biotechnology, 175(2), 705–714.

    Article  CAS  Google Scholar 

  19. Vukovic, N., Sukdolak, S., Solujic, S., & Niciforovic, N. (2010). Substituted imino and amino derivatives of 4-hydroxycoumarins as a novel antioxidant, antibacterial and antifungal agents: synthesis and in vitro assessments. Food Chemistry, 120(4), 1011–1018.

    Article  CAS  Google Scholar 

  20. Hassan, A. M., Nassar, A. M., Hussien, Y. Z., & Elkmash, A. N. (2012). Synthesis, characterization and biological evaluation of Fe(III), Co(II), Ni(II), Cu(II), and Zn(II) complexes with tetradentate Schiff base ligand derived from protocatechualdehyde with 2-aminophenol. Applied Biochemistry and Biotechnology, 167(3), 581–594.

    Article  CAS  Google Scholar 

  21. Joseph, J., & Nagashri, K. (2012). Novel copper-based therapeutic agent for anti-inflammatory: synthesis, characterization, and biochemical activities of copper(II) complexes of hydroxyflavone Schiff bases. Applied Biochemistry and Biotechnology, 167(5), 1446–1458.

    Article  CAS  Google Scholar 

  22. Arshad, N., Perveen, F., Saeed, A., Channar, P. A., Farooqi, S. I., Larik, F. A., & Mirza, B. (2017). Spectroscopic, molecular docking and structural activity studies of (E)-N′-(substituted benzylidene/methylene) isonicotinohydrazide derivatives for DNA binding and their biological screening. Journal of Molecular Structure, 1139, 371–380.

    Article  CAS  Google Scholar 

  23. Arshad, N., Channar, P. A., Saeed, A., Farooqi, S. I., Javeed, A., Larik, F. A., & Flörke, U. (2018). Structure elucidation, DNA binding, DFT, molecular docking and cytotoxic activity studies on novel single crystal (E)-1-(2-fluorobenzylidene) thiosemicarbazide. Journal of Saudi Chemical Society.

  24. Version, S.A. (2005). Version 2.1-4, SAINT+ version 7.23a and SADABS version 2004/1. Madison, Wisconsin, USA: Bruker Analytical Xray Systems, Inc..

    Google Scholar 

  25. Sheldrick, G. M. (2008). A short history of SHELX. Acta Crystallographica Section A: Foundations of Crystallography, 64(1), 112–122.

    CAS  Google Scholar 

  26. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., et al. (2009). Gaussian 09 revision a.1. Wallingford CT: Gaussian, Inc..

    Google Scholar 

  27. Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D., & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia.

  28. Bernstein, J., Davis, R. E., Shimoni, L., & Chang, N. L. (1995). Patterns in hydrogen bonding: functionality and graph set analysis in crystals. Angewandte Chemie International Edition in English, 34(15), 1555–1573.

    Article  CAS  Google Scholar 

  29. Hirshfeld, F. L. (1977). Bonded-atom fragments for describing molecular charge densities. Theoreticachimica Acta, 44(2), 129–138.

    CAS  Google Scholar 

  30. Spackman, M. A., & Jayatilaka, D. (2009). Hirshfeld surface analysis. CrystEngComm, 11(1), 19–32.

    Article  CAS  Google Scholar 

  31. Venkatesan, P., Thamotharan, S., Ilangovan, A., Liang, H., & Sundius, T. (2016). Crystal structure, Hirshfeld surfaces and DFT computation of NLO active (2E)-2-(ethoxycarbonyl)-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl) amino] prop-2-enoic acid. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 153, 625–636.

    Article  CAS  Google Scholar 

  32. Hathwar, V. R., Sist, M., Jørgensen, M. R., Mamakhel, A. H., Wang, X., Hoffmann, C. M., & Iversen, B. B. (2015). Quantitative analysis of intermolecular interactions in orthorhombic rubrene. IUCrJ, 2(5), 563–574.

    Article  CAS  Google Scholar 

  33. McKinnon, J. J., Jayatilaka, D., & Spackman, M. A. (2007). Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces. Chemical Communications, (37), 3814–3816.

  34. Abraham, C. S., Prasana, J. C., & Muthu, S. (2017). Quantum mechanical, spectroscopic and docking studies of 2-amino-3-bromo-5-nitropyridine by density functional method. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 181, 153–163.

    Article  CAS  Google Scholar 

  35. Abraham, C. S., Prasana, J. C., Muthu, S., & Raja, M. (2018). Quantum computational studies, spectroscopic (FT-IR, FT-Raman and UV–vis) profiling, natural hybrid orbital and molecular docking analysis on 2, 4 dibromoaniline. Journal of Molecular Structure, 1160, 393–405.

    Article  CAS  Google Scholar 

  36. Zhan, C. G., Nichols, J. A., & Dixon, D. A. (2003). Ionization potential, electron affinity, electronegativity, hardness, and electron excitation energy: molecular properties from density functional theory orbital energies. The Journal of Physical Chemistry A, 107(20), 4184–4195.

    Article  CAS  Google Scholar 

  37. Shah, N. A., Khan, M. R., Ahmad, B., Noureen, F., Rashid, U., & Khan, R. A. (2013). Investigation of flavonoid composition and anti-free radical potential of Sidacordata. BMC Complementary and Alternative Medicine, 13(1), 276.

    Article  Google Scholar 

  38. Arshad, N., Ahmad, M., Ashraf, M. Z., & Nadeem, H. (2014). Spectroscopic, electrochemical DNA binding and in vivo anti-inflammatory studies on newly synthesized Schiff bases of 4-aminophenazone. Journal of Photochemistry and Photobiology B: Biology, 138, 331–346.

    Article  CAS  Google Scholar 

  39. Arshad, N., Bhatti, M. H., Farooqi, S. I., Saleem, S., & Mirza, B. (2016). Synthesis, photochemical and electrochemical studies on triphenyltin (IV) derivative of (Z)-4-(4-cyanophenylamino)-4-oxobut-2-enoic acid for its binding with DNA: biological interpretation. Arabian Journal of Chemistry, 9(3), 451–462.

    Article  CAS  Google Scholar 

  40. Farooqi, S. I., Arshad, N., Channar, P. A., Perveen, F., Saeed, A., Larik, F. A., & Javeed, A. (2018). Synthesis, theoretical, spectroscopic and electrochemical DNA binding investigations of 1, 3, 4-thiadiazole derivatives of ibuprofen and ciprofloxacin: cancer cell line studies. Journal of Photochemistry and Photobiology B: Biology, 189, 104–118.

    Article  CAS  Google Scholar 

  41. Arshad, N., & Farooqi, S. I. (2018). Cyclic voltammetric DNA binding investigations on some anticancer potential metal complexes: a review. Applied Biochemistry and Biotechnology, 186(4), 1090–1110.

    Article  CAS  Google Scholar 

  42. Janjua, N. K., Shaheen, A., Yaqub, A., Perveen, F., Sabahat, S., Mumtaz, M., et al. (2011). Flavonoid–DNA binding studies and thermodynamic parameters. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 79(5), 1600–1604.

    Article  CAS  Google Scholar 

  43. Zhang, G., Guo, J., Pan, J., Chen, X., & Wang, J. (2009). Spectroscopic studies on the interaction of morin–Eu (III) complex with calf thymus DNA. Journal of Molecular Structure, 923(1–3), 114–119.

    Article  CAS  Google Scholar 

  44. Shahabadi, N., Hadidi, S., & Taherpour, A. (2014). Synthesis, characterization, and DNA binding studies of a new Pt(II) complex containing the drug levetiracetam: combining experimental and computational methods. Applied Biochemistry and Biotechnology, 172(5), 2436–2454.

    Article  CAS  Google Scholar 

  45. Chu, L. F., Shi, Y., Xu, D. F., Yu, H., Lin, J. R., & He, Q. Z. (2015). Synthesis and biological studies of some lanthanide complexes of Schiff base. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 45(11), 1617–1626.

    Article  CAS  Google Scholar 

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Acknowledgements

The authors would like to thank all the mentioned departments of national and international universities/institutes for the accomplishment of research explored in this paper.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Pervaiz Ali Channar, Fayaz Ali Larik, Aamer Saeed, Syeda Aaliya Shehzadi & Nasir Abbas

  2. Department of Chemistry, Faculty of Sciences, Allama Iqbal Open University, Islamabad, 44000, Pakistan

    Nasima Arshad & Shahid Iqbal Farooqi

  3. Department of Physics, Faculty of Engineering, Hacettepe University, 06800, Beytepe, Ankara, Turkey

    Tuncer Hökelek

  4. Sulaiman Bin Abdullah Aba Al-Khail-Centre for Interdisciplinary Research in Basic Sciences (SA-CIRBS), International Islamic University, Islamabad, Islamabad, Pakistan

    Syeda Aaliya Shehzadi

  5. Department Chemie, Fakultätfür Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, 33098, Paderborn, Germany

    Ulrich Flörke

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  1. Pervaiz Ali Channar
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Channar, P.A., Arshad, N., Farooqi, S.I. et al. Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT, and DNA-Binding Studies of (E)-2-(3-Hydroxy-4-Methoxybenzylidene)Hydrazinecarbothioamide. Appl Biochem Biotechnol 189, 175–192 (2019). https://doi.org/10.1007/s12010-019-03008-y

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