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Synthesis, spectroscopic (FT-IR and NMR), DFT and molecular docking studies of ethyl 1-(3-nitrophenyl)-5-phenyl-3-((4-(trifluoromethyl)phenyl)carbamoyl)-1H-pyrazole-4-carboxylate

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Abstract

Trifluoromethyl group containing pyrazole-3-carboxamide derivative is synthesized and the structure of the molecule (E3N5PC) has been verified by using FT-IR, 1H NMR, 13C NMR spectroscopic methods and elemental analysis. In order to determine the theoretical characterization, spectroscopic and electronic properties of the title compound, DFT calculations employing B3LYP method with 6-311 + + G(d, p) basis set has been carried out by utilizing Gaussian 09w package program. In addition, VEDA 4xx software has been used to determine the vibrational frequencies of the title molecule with potential energy distribution percentage. Chemical selectivity and reactivity of the drug molecule, which helps to improve the stability of the molecule, are analyzed via NBO calculations. Molecular docking is to find the best fit orientation of the title molecule with the cannabinoid receptor1.

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References

  1. S. Fustero, M. Sanchez-Rosello, P. Barrio, A. Simon-Fuentes, Chem. Rev. 111, 6984 (2011)

    Article  CAS  PubMed  Google Scholar 

  2. S. Fustero, A. Simon-Fuentes, J.F. Sanz-Cervera, Org. Prep. Proced. Int. 41(4), 253 (2009)

    Article  CAS  Google Scholar 

  3. S. Mert, R. Kasimogullari, S. Ok, J. Postdr. Res. 2(4), 64 (2014)

    Google Scholar 

  4. R. Nithyabalaji, H. Krishnan, R. Sribalan, J. Mol. Struct. 1186, 1 (2019)

    Article  CAS  Google Scholar 

  5. K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y.N. Mabkhot, F.A. Al-Aizari, M. Ansar, Molecules 23(1), 134 (2018)

    Article  PubMed Central  CAS  Google Scholar 

  6. F.E. Bennani, L. Doudach, Y. Cherrah, Y. Ramli, K. Karrouchi, M. Ansar, M.E.A. Faouzi, Bioorg. Chem. 97, 103470 (2020)

    Article  CAS  PubMed  Google Scholar 

  7. A. Bekhit, A. Hymete, E.D.A. Bekhit, A. Damtew, Y.H. Aboul-Enein, Mini Rev. Med. Chem. 10(11), 1014 (2010)

    Article  CAS  PubMed  Google Scholar 

  8. M. Abdel-Aziz, G.E.D.A. Abuo-Rahma, A.A. Hassan, Eur. J. Med. Chem. 44(9), 3480 (2009)

    Article  CAS  PubMed  Google Scholar 

  9. D.K. Aneja, P. Lohan, S. Arora, C. Sharma, K.R. Aneja, O. Prakash, Org. Med. Chem. Lett. 1(1), 15 (2011)

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  10. F.K. Keter, J. Darkwa, Biometals 25(1), 9 (2012)

    Article  CAS  PubMed  Google Scholar 

  11. S.G. Küçükgüzel, S. Şenkardeş, Eur. J. Med. Chem. 97, 786 (2015)

    Article  PubMed  CAS  Google Scholar 

  12. H. Kumar, D. Saini, S. Jain, N. Jain, Eur. J. Med. Chem. 70, 248 (2013)

    Article  CAS  PubMed  Google Scholar 

  13. G.M. Nitulescu, C. Draghici, O.T. Olaru, Int. J. Mol. Sci. 14(11), 21805 (2013)

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  14. P.D. Sauzem, P. Machado, M.A. Rubin, G.D.S. Sant’Anna, H.B. Faber et al., Eur. J. Med. Chem. 43(6), 1237 (2008)

    Article  CAS  PubMed  Google Scholar 

  15. D. Secci, A. Bolasco, P. Chimenti, S. Carradori, Curr. Med. Chem. 18(33), 5114 (2011)

    Article  CAS  PubMed  Google Scholar 

  16. S. Mert, R. Kasımoğulları, T. Iça, F. Çolak, A. Altun, S. Ok, Eur. J. Med. Chem. 78, 86 (2014)

    Article  CAS  PubMed  Google Scholar 

  17. A. Bayrakdar, H.H. Kart, S. Elcin, H. Deligoz, M. Karabacak, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 136, 607 (2015)

    Article  CAS  Google Scholar 

  18. B. Sathya, S. Karthi, K. Ajaijawahar, M. Prasath, Res. Chem. Intermed. 46(10), 4475 (2020)

    Article  CAS  Google Scholar 

  19. M. Govindammal, M. Prasath, S. Kamaraj, B. Sathya, Biocatal. Agric. Biotechnol. 18, 101086 (2019)

    Article  Google Scholar 

  20. B. Sathya, M. Prasath, Res. Chem. Intermed. 47, 2775 (2021)

    Article  CAS  Google Scholar 

  21. B. Sathya, M. Prasath, Res. Chem. Intermed. 45, 2135 (2019)

    Article  CAS  Google Scholar 

  22. G. Mol, D. Aruldhas, Bull. Pure Appl. Sci. Chem. 37(1), 20 (2018)

    Article  Google Scholar 

  23. J.I. Ahamed, M.F. Valan, K. Pandurengan et al., Res. Chem. Intermed. 47, 759 (2021)

    Article  CAS  Google Scholar 

  24. R. Kasımoğulları, H. Duran, A.S. Yağlıoğlu, S. Mert, I. Demirtaş, Chem. Month. 146(10), 1743 (2015)

    Article  CAS  Google Scholar 

  25. R. Kasımoğulları, M. Maden, A.S. Yağlıoğlu, S. Mert, I. Demirtaş, Indian J. Chem. 54B, 1134 (2015)

    Google Scholar 

  26. R. Kasımoğulları, M. Bülbül, S. Mert, H. Güleryüz, J. Enzyme Inhib. Med. Chem. 26(2), 231 (2011)

    Article  PubMed  CAS  Google Scholar 

  27. Gaussian09 RA. 1, mj frisch, gw trucks, hb schlegel, ge scuseria, ma robb, jr cheeseman, g. Scalmani, v. Barone, b. Mennucci, ga petersson et al., (gaussian. Inc, Wallingford CT, 2009)

  28. A. Frisch, A. Nielsen, A. Holder, Gauss View Molecular Visualization Program User Manual (Gaussian Inc, Pittsburg, 2001)

    Google Scholar 

  29. M.H. Jamróz, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 114, 220 (2013)

    Article  CAS  Google Scholar 

  30. F. Scalambra, S. Rudić, A. Romerosa, Eur. J. Inorg. Chem. 2019(8), 1155 (2019)

    Article  CAS  Google Scholar 

  31. D. Lin-Vien, N.B. Colthup, W.G. Fateley, J.G. Grasselli, The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules (Elsevier, 1991)

    Google Scholar 

  32. N.P. Roeges, J. Baas, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures (Wiley, 1994)

    Google Scholar 

  33. S.E. Krikorian, M. Mahpour, Spectrochim. Acta Part A Mol. Spectrosc. 29(7), 1233 (1973)

    Article  CAS  Google Scholar 

  34. T. Miyazawa, J. Mol. Spectrosc. 4(1–6), 168 (1960)

    Article  CAS  Google Scholar 

  35. B.C. Smith, Infrared Spectral Interpretation: A Systematic Approach (CRC Press, 1998)

    Google Scholar 

  36. T.B. Issa, F. Sayari, H. Ghalla, L. Benhamada, J. Mol. Struct. 1178, 436 (2019)

    Article  CAS  Google Scholar 

  37. B. Nie, J. Stutzman, A. Xie, Biophys. J. 88(4), 2833 (2005)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. K.-I. Takei, R. Takahashi, T. Noguchi, J. Phys. Chem. B 112(21), 6725 (2008)

    Article  CAS  PubMed  Google Scholar 

  39. N. Issaoui, H. Ghalla, F. Bardak, M. Karabacak, N.A. Dlala et al., J. Mol. Struct. 1130, 659 (2017)

    Article  CAS  Google Scholar 

  40. N. Sundaraganesan, K.S. Kumar, C. Meganathan, B.D. Joshua, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 65(5), 1186 (2006)

    Article  CAS  Google Scholar 

  41. N. Wu, X. She, D. Yang, X. Wu, F. Su, Y. Chen, J. Mater. Chem. 22(33), 17254 (2012)

    Article  CAS  Google Scholar 

  42. V. Aswathy, Y.S. Mary, P. Jojo, C.Y. Panicker, A. Bielenica et al., J. Mol. Struct. 1134, 668 (2017)

    Article  CAS  Google Scholar 

  43. Y.S. Mary, V. Aswathy, C.Y. Panicker, A. Bielenica, P. Brzózka et al., RSC Adv. 6(113), 111997 (2016)

    Article  CAS  Google Scholar 

  44. Y.S. Mary, C.Y. Panicker, T. Yamuna, M. Siddegowda, H. Yathirajan et al., Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 132, 491 (2014)

    Article  CAS  Google Scholar 

  45. V. Baron, M. Cossi, J. Tomasi, J. Chem. Phys. 107(8), 3210 (1997)

    Article  Google Scholar 

  46. H. Sklenar, J. Jäger, Int. J. Quantum Chem. 16(3), 467 (1979)

    Article  CAS  Google Scholar 

  47. I. Fleming, Molecular Orbitals and Organic Chemical Reactions (Wiley, 2011)

    Google Scholar 

  48. D. Sajan, L. Joseph, N. Vijayan, M. Karabacak, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 81(1), 85 (2011)

    Article  CAS  Google Scholar 

  49. N. Subramanian, N. Sundaraganesan, J. Jayabharathi, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 76(2), 259 (2010)

    Article  CAS  Google Scholar 

  50. L.D. Mendelsohn, J. Chem. Inf. Comput. Sci. 44(6), 2225 (2004)

    Article  CAS  Google Scholar 

  51. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew et al., J. Comput. Chem. 30(16), 2785 (2009)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  52. S.M.D. Rizvi, S. Shakil, M.A. Haneef, EXCLI J. 12, 831 (2013)

    PubMed  PubMed Central  Google Scholar 

  53. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt et al., J. Comput. Chem. 25(13), 1605 (2004)

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Vocational School of Higher Education for Healthcare Services, Igdir University, 76100, Igdir, Turkey

    Alpaslan Bayrakdar

  2. Altintas Vocational School, Kütahya Dumlupınar University, 43800, Kütahya, Turkey

    Samet Mert

  3. Faculty of Arts and Sciences, Kütahya Dumlupınar University, 43100, Kütahya, Turkey

    Rahmi Kasımoğulları

  4. Department of Physics, Periyar University PG Extension Centre, Dharmapuri, Tamilnadu, 636701, India

    Sathya Bangaru & Prasath Manivannan

  5. SSN Research Centre, SSN College of Engineering, Kalavakkam, Chennai, Tamilnadu, 603110, India

    Sathya Bangaru

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  1. Alpaslan Bayrakdar
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  5. Prasath Manivannan
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Correspondence to Alpaslan Bayrakdar or Prasath Manivannan.

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Bayrakdar, A., Mert, S., Kasımoğulları, R. et al. Synthesis, spectroscopic (FT-IR and NMR), DFT and molecular docking studies of ethyl 1-(3-nitrophenyl)-5-phenyl-3-((4-(trifluoromethyl)phenyl)carbamoyl)-1H-pyrazole-4-carboxylate. Res Chem Intermed 48, 2087–2109 (2022). https://doi.org/10.1007/s11164-022-04681-1

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