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Vibrational Spectra of 3-(Adamantan-1-YL)-4-(2-Propen-1-YL)-1H-1,2,4-Triazole-5(4H)-Thione

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Journal of Applied Spectroscopy Aims and scope

Vibrational spectra of 3-(adamantan-1-yl)-4-(2-propen-1-yl)-1H-1,2,4-triazole-5(4H)-thione (C15H21N3S), which was promising for drug development, were studied experimentally and theoretically. The geometric structure and normal modes of the molecule and its dimer were calculated using quantum-mechanical density functional theory. It was shown that the experimentally obtained vibrational spectra were due to dimeric C15H21N3S structures. This conclusion was confirmed by spectra of the isotopically substituted compound with a deuterated imine. Bands at 1496 and 1549 cm–1 were identified as markers of dimer formation. Bands at 936 and 1244 cm–1 were found to be markers of intermolecular interactions of adamantane fragments.

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References

  1. G. Lamoureux and G. Artavia, Curr. Med. Chem., 17, 2967–2978 (2010).

    Article  Google Scholar 

  2. K. V. Derpoorten, J. Balzarini, E. D. Clercq, and J. H. Poupaert, Biomed. Pharmacother., 51, 464 (1997).

    Article  Google Scholar 

  3. E. B. Vilhauer, J. A. Brinkman, G. B. Naderi, B. F. Burkey, B. E. Dunning, K. Prasad, B. L. Mangold, M. E. Russell, and T. E. Hughes, J. Med. Chem., 46, 2774–2789 (2003).

    Article  Google Scholar 

  4. E. Antoniadou-Vyza, P. Tsitsa, E. Hytiroglou, and A. Tsantili-Kakoulidou, Eur. J. Med. Chem., 31, 105 (1996).

    Article  Google Scholar 

  5. A. A. Kadi, N. R. El-Brollosy, O. A. Al-Deeb, E. E. Habib, T. M. Ibrahim, and A. A. El-Emam, Eur. J. Med. Chem., 42, 235 (2007).

    Article  Google Scholar 

  6. S. Y. Sun, P. Yue, X. Chen, W. K. Hong, and R. Loran, Cancer Res., 62, 2430 (2002).

    Google Scholar 

  7. J. Bormann, Eur. J. Pharmacol., 166, 591–592 (1989).

    Article  Google Scholar 

  8. D. S. Schiller and Y. B. Fung, Clin. Ther., 29, 1862–1886 (2007).

    Article  Google Scholar 

  9. P. C. Wade, B. R. Vogt, N. P. Kissick, L. M. Simpkins, and D. M. Palmers, J. Med. Chem., 25, 331–333 (1982).

    Article  Google Scholar 

  10. B. Tozkoparan, E. Kupeli, E. Yesilada, and M. Ertan, Bioorg. Med. Chem., 15, 1808–1814 (2007).

    Article  Google Scholar 

  11. L. L. Gladkov, S. V. Gaponenko, E. V. Shabunya-Klyachkovskaya, A. N. Shimko, E. S. Al-Abdullah, and A. A. El-Emam, Spectrochim. Acta, Part A, 128, 874–879 (2014).

    Article  ADS  Google Scholar 

  12. F. A. M. Al-Omary, Y. S. Mary, C. Y. Panicker, A. A. El-Emam, I. A. Al-Swaidan, A. A. Al-Saadi, and C. V. Alsenoy, J. Mol. Struct., 1096, 1–14 (2015).

    Article  ADS  Google Scholar 

  13. M. S. Almutairi, A. M. Alanazi, E. S. Al-Abdullah, A. A. El-Emam, S. K. Pathak, R. Srivastava, O. Prasad, and L. Sinha, Spectrochim. Acta, Part A, 140, 1–14 (2015).

    Article  ADS  Google Scholar 

  14. S. V. Gaponenko, A. V. Glinistyi, E. V. Shabunya-Klyachkovskaya, and M. B. Shundalov, in: Proc. Int. Conf. "Fundamental Problems in Optics – 2014" [in Russian], Oct. 20–24, 2014, St. Petersburg (2014), pp. 83–84.

  15. M. S. Almutairi, M. M. Al-Shehri, A. A. El-Emam, S. W. Ng, and E. R. T. Tiekin, Acta Crystallogr., Sect. E: Struct. Rep. Online, 68, o656 (2012).

  16. S. H. R. Sebastian, Sr., M. I. Attia, M. S. Almutairi, A. A. El-Emam, C. Y. Panicker, I. A. Al-Swaidan, A. A. Al-Saadi, and C. V. Alsenoy, Spectrochim. Acta, Part A, 132, 295–304 (2014).

  17. L. Bistricic, G. Baranovic, and K. Mlinaric-Majerski, Spectrochim. Acta, Part A, 51, 1643–1664 (1995).

  18. D. N. Laikov, Chem. Phys. Lett., 281, 151–156 (1997).

    Article  ADS  Google Scholar 

  19. D. N. Laikov, "Development of an Economical Approach to Density-Functional Calculation of Molecules and Its Use to Solve Complicated Chemical Problems," Candidate′s Dissertation, Moscow (2000).

  20. K. Bahgat and S. Fraihat, Spectrochim. Acta, Part A, 135, 1145–1155 (2015).

  21. L. L. Gladkov, A. T. Gradyushko, A. M. Shulga, K. N. Solovyov, and A. S. Starukhin, J. Mol. Struct., 47, 463–493 (1978).

  22. K. N. Solov′ev, L. L. Gladkov, A. S. Starukhin, and S. F. Shkirman, Spectroscopy of Porphyrins: Vibrational States [in Russian], Nauka i Tekhnika, Minsk (1985), pp. 241–246.

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Authors and Affiliations

  1. Belarusian State Academy of Communications, 8-2 F. Skorina St., Minsk, 220114, Belarus

    L. L. Gladkov

  2. B. I. Stepanov Institute of Physics, National Academy of Sciences of Belarus, Minsk, Belarus

    A. S. Matsukovich, T. A. Pavich & S. V. Gaponenko

  3. College of Pharmacy, King Saud University, Riyadh, Saudi Arabia

    A. A. El-Emam

Authors
  1. L. L. Gladkov
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  2. A. S. Matsukovich
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  3. T. A. Pavich
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  4. S. V. Gaponenko
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  5. A. A. El-Emam
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Correspondence to L. L. Gladkov.

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Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 83, No. 6, pp. 869–876, November–December, 2016.

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Gladkov, L.L., Matsukovich, A.S., Pavich, T.A. et al. Vibrational Spectra of 3-(Adamantan-1-YL)-4-(2-Propen-1-YL)-1H-1,2,4-Triazole-5(4H)-Thione. J Appl Spectrosc 83, 924–930 (2017). https://doi.org/10.1007/s10812-017-0385-7

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  • DOI: https://doi.org/10.1007/s10812-017-0385-7

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