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Synthesis and crystal structure of bis-chalcone-derived fused-ring pyrazoline having an unusual substitution pattern

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Abstract

Pyrazolines are an important class of heterocyclic compounds with diverse applications. A novel bis-chalcone-derived fused ring pyrazoline has been obtained by the reaction of bis-chalcone with hydrazine hydrate in acetic acid solvent having a catalytic amount of HCl and characterized by IR, 1H and 13C NMR, GC–MS, and finally by X-ray single crystal analysis. Interestingly, the in situ post-cyclization substitution pattern on pyrazoline ring nitrogen is entirely different from the previously reported related pyrazoline derivatives. The new compound crystallizes out from its ethanolic solution, which has monoclinic crystal lattice with P21/c space group, a = 6.1001(4) Å, b = 38.602(2) Å, c = 7.7332(5) Å, α = 90°, β = 113.039(3)°, γ = 90°, V = 1675.73(19) Å3, Z = 4, crystal size = 0.38 × 0.30 × 0.18 mm3, and R int = 0.043.

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References

  1. Elinson MN, Nasybullin RF, Ryzhkov FV, Zaimovskaya TA, Nikishin GI (2015) Monatsh Chem 146:631

    Article  CAS  Google Scholar 

  2. Albuquerque HMT, Santos CMM, Cavaleiro JAS, Silva AMS (2014) Curr Org Chem 18:2750

    Article  CAS  Google Scholar 

  3. Seebacher W, Michl G, Belaj F, Brun R, Saf R, Weis R (2003) Tetrahedron 59:2811

    Article  CAS  Google Scholar 

  4. Tong X, Chen R, Zhang TT, Han Y, Tang WJ, Liu XH (2015) Bioorg Med Chem 23:515

    Article  CAS  Google Scholar 

  5. Montoya A, Quiroga J, Abonia R, Derita M, Sortino M, Ornelas A, Zacchino S, Insuasty B (2016) Molecules 21:969

    Article  Google Scholar 

  6. Kaplancikli ZA, Ozdemir A, Turan-Zitouni G, Altintop MD, Can OD (2010) Eur J Med Chem 45:4383

    Article  CAS  Google Scholar 

  7. Bhandari S, Tripathi AC, Saraf SK (2013) Med Chem Res 22:5290

    Article  CAS  Google Scholar 

  8. Jadhav SY, Shirame SP, Kulkarni SD, Patil SB, Pasale SK, Bhosale RB (2013) Bioorg Med Chem Lett 23:2575

    Article  CAS  Google Scholar 

  9. Evranos-Aksoz B, Onurdag FK, Ozgacar SO (2015) Z Naturforsch C 70:183

    Article  CAS  Google Scholar 

  10. Elmeligie S, Khalil NA, Ahmed EM, Emam SH, Zaitone SAB (2016) Biol Pharm Bull 39:1611

    Article  CAS  Google Scholar 

  11. Bruno O, Bondavalli F, Ranise A, Schenone P, Losasso C, Cilenti L, Matera C, Marmo E (1990) Farmaco 45:147

    CAS  Google Scholar 

  12. Harikrishna N, Isloor AM, Ananda K, Obaid A, Fun HK (2016) New J Chem 40:73

    Article  CAS  Google Scholar 

  13. Ahn JH, Kim HM, Jung SH, Kang SK, Kim KR, Rhee SD, Yang SD, Cheon HG, Kim SS (2004) Bioorg Med Chem Lett 14:4461

    Article  CAS  Google Scholar 

  14. Amr AE, AL-Omar MA, Abdalla MM (2016) Lat Am J Pharm 35:950

    Google Scholar 

  15. Lee Y, Kim BS, Ahn S, Koh D, Lee YH, Shin SY, Lim Y (2016) Bioorg Chem 68:166

    Article  CAS  Google Scholar 

  16. Havrylyuk D, Zimenkovsky B, Vasylenko O, Lesyk R (2013) J Heterocycl Chem 50:E55

    Article  CAS  Google Scholar 

  17. Mete E, Comez B, Gul HI, Gulcin I, Supuran CT (2016) J Enz Inhib Med Chem 31:1

    Article  CAS  Google Scholar 

  18. Szukalski A, Haupa K, Miniewicz A, Mysliwiec J (2015) J Phys Chem C 119:10007

    Article  CAS  Google Scholar 

  19. Szukalski A, Miniewicz A, Haupa K, Przybyl B, Janczak J, Sobolewski AL, Mysliwiec J (2016) J Phys Chem C 120:14813

    Article  CAS  Google Scholar 

  20. Afsah EM, Kandeel EEDM, Khalifa MM, Hammouda WM (2007) Z Naturforsch B 62:540

    Article  CAS  Google Scholar 

  21. Levai A (2002) J Heterocycl Chem 39:1

    Article  CAS  Google Scholar 

  22. Abbas A, Flores-Holguin N, Naseer MM (2015) New J Chem 39:4359

    Article  CAS  Google Scholar 

  23. Abbas A, Hussain S, Hafeez N, Naseer MM (2014) Spectrochim Acta A 133:182

    Article  CAS  Google Scholar 

  24. Abbas A, Hussain S, Hafeez N, Hasan A, Naseer MM (2014) Spectrochim Acta A 127:32

    Article  CAS  Google Scholar 

  25. Abbas A, Nazir H, Naseer MM, Bolte M, Hussain S, Hafeez N, Hasan A (2014) Spectrochim Acta A 120:176

    Article  CAS  Google Scholar 

  26. Abbas A, Naseer MM (2014) Acta Chim Slov 61:792

    CAS  Google Scholar 

  27. Anam F, Abbas A, Lo KM, Zia-ur-Rehman, Hameed S, Naseer MM (2014) New J Chem 38:5617

    Article  CAS  Google Scholar 

  28. Song J, Zhao PS, Zhang WG (2010) Bull Korean Chem Soc 31:1875

    Article  CAS  Google Scholar 

  29. Asiri AM, Khan SA (2012) J Heterocycl Chem 49:1434

    Article  CAS  Google Scholar 

  30. Asiri AM, Khan SA (2011) Molecules 16:523

    Article  CAS  Google Scholar 

  31. Azam MA, Gomathy S, Alam F, Suresh B (2008) Indian J Heterocycl Chem 18:157

    CAS  Google Scholar 

  32. Hadi S, Rilyanti M (2010) Orient J Chem 26:775

    CAS  Google Scholar 

  33. Hadi S, Afriyani H, Anggraini WD, Qudus HI, Suhartati T (2015) Asian J Chem 27:1509

    Article  CAS  Google Scholar 

  34. Naseer MM, Hameed S (2012) Cryst Eng Comm 14:4247

    Article  CAS  Google Scholar 

  35. Ahmad M, Pervez H, Hadda TB, Toupet L, Naseer MM (2014) Tetrahedron Lett 55:5400

    Article  CAS  Google Scholar 

  36. Sheldrick GM (2008) Acta Crystallogr A 64:112

    Article  CAS  Google Scholar 

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Acknowledgements

We are grateful to HEC and QAU for financial support.

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Authors and Affiliations

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

    Shumaila Ashraf, Shahid Hameed & Muhammad Moazzam Naseer

  2. Department of Physics, University of Sargodha, Sargodha, 40100, Pakistan

    Muhammad Nawaz Tahir

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  1. Shumaila Ashraf
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  2. Shahid Hameed
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  3. Muhammad Nawaz Tahir
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  4. Muhammad Moazzam Naseer
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Correspondence to Muhammad Moazzam Naseer.

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Ashraf, S., Hameed, S., Tahir, M.N. et al. Synthesis and crystal structure of bis-chalcone-derived fused-ring pyrazoline having an unusual substitution pattern. Monatsh Chem 148, 1871–1875 (2017). https://doi.org/10.1007/s00706-017-1995-8

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  • DOI: https://doi.org/10.1007/s00706-017-1995-8

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