Advertisement

Research on Chemical Intermediates

, Volume 43, Issue 11, pp 6131–6154 | Cite as

Synthesis, crystal structure and molecular docking studies of novel 2-(4-(4-substitutedphenylsulfonyl)piperazin-1-yl)quinolone-3-carbaldehyde derivatives

  • Nivedita Rathnakar Desai
  • Krishnaswamy Gurunathan
  • Parameshwar Adimule Suchetan
  • Aruna Kumar Doyjide Basappa
  • Shivalingegowda Naveen
  • Neratur Krishnappagowda Lokanath
  • Swamy Sreenivasa
Article

Abstract

The present work reports the synthesis of novel 2-(4-(4-substitutedphenylsulfonyl) piperazin-1-yl) quinolone-3-carbaldehyde derivatives, namely, 2-(4-tosylpiperazin-1-yl)quinoline-3-carbaldehyde (4a), 2-(4-(4-nitrophenylsulfonyl)piperazin-1-yl)quinoline-3-carbaldehyde (4b) and 2-(4-(4-tert-butylphenylsulfonyl) piperazin-1-yl)quinoline-3-carbaldehyde (4c). These compounds have been characterized by FT-IR, 1H-NMR, 13C-NMR and LCMS. Further, the structures of compounds 4b and 4c have been elucidated by single crystal X-ray diffraction studies. The asymmetric unit of 4b contains two molecules (A and B) and that of 4c contains one. The piperazine ring in both the molecules 4b and 4c has chair conformation and the aldehyde group is twisted with respect to the quinoline group, respectively, by 13.3 (3)°, 18.2 (3)° and 11.2 (3)° in Molecule A & B of 4b and 4c due to the bulky piperazinyl group present in the ortho position. The crystal structures of both features interactions of the type C-H…O, C-H…πaryl and πaryl… πaryl, leading to a three-dimensional (3D) supramolecular architecture in 4b and a one-dimensional (1D) architecture in 4c. The various intermolecular interactions exhibited in 4b and 4c are well supported by Hirshfeld surface and fingerprint plots analysis. Further, the three compounds were evaluated for their in-silico antimicrobial activity. In-silico molecular docking studies were carried out in order to know the binding modes of the synthesized compounds with DNA Gyrase A and N-myristoyltranferase as target proteins for antibacterial and antifungal docking studies, respectively.

Keywords

2-(4-(4-substitutedphenylsulfonyl)piperazin-1-yl)quinolone-3-carbaldehyde In-silico molecular docking studies Crystal structure Hirshfeld surfaces Antibacterial activity Antifungal activity 

Notes

Acknowledgements

The authors acknowledge I.O.E., Vijnana Bhavana, University of Mysore, Mysuru-6 for single-crystal X-ray data collection. Also the laboratory facilities provided to carry out research work by Tumkur University are greatly acknowledged.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11164_2017_2981_MOESM1_ESM.docx (627 kb)
Supplementary material 1 (DOCX 627 kb)

References

  1. 1.
    A. Kumar, K. Srivastava, R. Kumar, S.K. Puri, P.M.S. Chauhan, Bioorg. Med. Chem. Lett. 20, 7059 (2010)CrossRefGoogle Scholar
  2. 2.
    R. Arancibia, F. Dubar, B. Pradines, I. Forfar, D. Dive, A.H. Klahn, Bioorg. Med. Chem. 18, 8085 (2010)CrossRefGoogle Scholar
  3. 3.
    P.A. Leatham, H.A. Bird, V. Wright, D. Seymour, A. Gordon, Eur. J. Rheumatol. Inflamm. 6, 209 (1983)Google Scholar
  4. 4.
    W.A. Denny, W.R. Wilson, D.C. Ware, G.J. Atwell, J.B. Milbank, R.J. Stevenson. U.S Patent 7064117, (2006)Google Scholar
  5. 5.
    V.R. Solomon, C.H.H. Lee, Bioorg. Med. Chem. 18, 1563 (2010)CrossRefGoogle Scholar
  6. 6.
    A. Mahamoud, J. Chevalier, A. Davin-Regli, J. Barbe, J.-M. Pages, Curr. Drug Targ. 7, 843 (2006)CrossRefGoogle Scholar
  7. 7.
    W.D. Wilson, M. Zhao, S.E. Patterson, R.L. Wydra, L. Janda, L. Strekowski, Med. Chem. Res. 2, 102 (1992)Google Scholar
  8. 8.
    L. Strekowski, J.L. Mores, V.A. Honkan, A. Czarny, M.T. Cegla, S.E. Patterson, R.L. Wydra, R.F. Schinazi, J. Med. Chem. 34, 1739 (1991)CrossRefGoogle Scholar
  9. 9.
    A. Wilhelmsson, J. Goos-Nilsson, Wrobel. Bioorg. Med. Chem. Lett. 20, 209 (2010)CrossRefGoogle Scholar
  10. 10.
    S. Gemmaa, S. Butini, G. Campiani, M. Brindisi, S. Zanoli, M. Pia Romano, P. Tripaldi, L. Savini, I. Fiorini, G. Borrelli, E. Novellino, G. Maga, Bioorg. Med. Chem. Lett. 21, 2776 (2011)CrossRefGoogle Scholar
  11. 11.
    F. Sliman, M. Blairvacq, E. Durieu, L. Meijer, J. Rodrigo, D. Desmaële, Bioorg. Med. Chem. Lett. 20, 2801 (2010)CrossRefGoogle Scholar
  12. 12.
    Y. Yang, L. Shi, Y. Zhou, H.-Q. Li, Z.-W. Zhu, H.-L. Zhu, Bioorg. Med. Chem. Lett. 20, 6653 (2010)CrossRefGoogle Scholar
  13. 13.
    B. Alka, A.B. Sharma, S.D. Reddy, A. Singh, A. S, Eur. J. Med. Chem. 45, 2656 (2010)CrossRefGoogle Scholar
  14. 14.
    S. Jacek, F. Barbara, L. Nowinski, Pharmacol Rep. 63, 455 (2011)Google Scholar
  15. 15.
    G.S. Hassan, IntJ Pharm Pharm Sci. 3(4), 441 (2011)Google Scholar
  16. 16.
    S.D. Desai, A.M. Mehta, Res. J. Chem. Sci. 4(5), 14 (2014)Google Scholar
  17. 17.
    A. Pietrzycka, M.S.T. Pietrzycka, A.M. Waszkielewicz, H. Marona, Acta Pol Drug Res. 63(1), 19 (2006)Google Scholar
  18. 18.
    W. Cunico, C.R. Gomes, W.T. Harrison, M. Wardell, J.L. Wardell, S.M. Waedell, Z KRIST 224(9), 461 (2009)CrossRefGoogle Scholar
  19. 19.
    C. Meri Koksal Akkoc, M.Y. Yukse, I. Durmaz, R. Cetin Atalay, J. Med. Chem. 52(23), 7817 (2009)CrossRefGoogle Scholar
  20. 20.
    K.R. Varadaraju, J.R. Kumar, L. Mallesha, A. Muruli, K.N. Mohana, C.K. Mukunda, U. Sharanaiah, Int J Alzheimers Dis., Article ID 653962, 1 (2012)Google Scholar
  21. 21.
    F. Berardi, C. Abate, S. Ferorelli, V. Uricchio, N.A. Colabufo, M. Niso, R. Perron, J. Med. Chem. 52(23), 7817 (2009)CrossRefGoogle Scholar
  22. 22.
    S.A. Jeon, H.A. Choo, W.K. Park, H.W. Rhim, S.Y. Ko, Y.S. Cho, H.Y. Koh, A.N. Pae, Bull. Korean Chem. Soc. 28(2), 285 (2007)CrossRefGoogle Scholar
  23. 23.
    J.J. Marugan, W. Zheng, O. Motabar, N. Southall, E. Goldin, W. Westbroek, B.K. Stubblefield, E. Sidransky, R.A. Aungst, W. Lea, W. Lea, A. Simeonov, W. Leister, C.P. Austin, J. Med. Chem. 54(4), 1033 (2011)CrossRefGoogle Scholar
  24. 24.
    V.S.R. Nirogi, A.D. Deshpande, A.K. Chindhe, R. Kambhampati, A.K. Shinde, P.K. Dubey, Der Pharma Chem. 4(3), 909 (2012)Google Scholar
  25. 25.
    A.M. Qandil, Pharmaceuticals 5, 460 (2012)CrossRefGoogle Scholar
  26. 26.
    S. Berg, M. Bergh, S. Hellberg, K. Hogdin, Y. Lo-Alfredsson, P. Soderman, S. von Berg, T. Weigelt, M. Ormo, Y. Xue, J. Tucker, J. Neelissen, E. Jerning, Y. Nilsson, R. Bhat, J. Med. Chem. 55, 9107 (2012)CrossRefGoogle Scholar
  27. 27.
    M.M.J. Al-Mudhafar, M.Q. Abdulkadir, A.A. Mohammed, F.A. Al-hilli, A.M. Hussian, Pharmacie Globale (IJCP) 6(2), 1 (2009)Google Scholar
  28. 28.
    C.S. Anandakumar, S.B. Benaka Prasad, K. Vinay, S. Chandrappa, N.R. Thimmegowda, Y.C. Sunil Kumar, S. Swarup, K.S. Rangappa, Eur. J. Med. 44, 1223 (2009)CrossRefGoogle Scholar
  29. 29.
    Z.-K. Wan, E. Chenail, H.-Q. Li, M. Ipek, J. Xiang, V. Suri, S. Hahm, J. Bard, K. Svenson, X. Xu, X. Tian, M. Perreault, T.S. Mansour, J. Tobin, E. Saiah, Med. Chem. Lett. 4, 118 (2013)CrossRefGoogle Scholar
  30. 30.
    B. Kandagatla, S.C. Rao, K.M. Kumar, N. Mulakayala, Der Pharma Chemica 4(6), 2502 (2012)Google Scholar
  31. 31.
    P. Zajdel, K. Marciniec, A. Maslankiewicz, K. Grychowska, G. Satala, B. Duszynska, T. Lenda, A. Siwek, G. Nowak, A. Partyka, A. Wesolowska, M. Pawlowski, Eur. J. Med. 60, 42 (2013)CrossRefGoogle Scholar
  32. 32.
    H. Eshghia, M. Rahimizadeha, M. Zokaeib, S. Eshghic, S. Eshghic, Z. Faghihia, E. Tabasib, M. Kihanyana, Eur. J. Chem. 2(1), 47 (2011)CrossRefGoogle Scholar
  33. 33.
    A. Kamal, P. Swapna, R. Shetti, A.B. Shaik, M.P. Narasimha Rao, S. Gupta, Eur. J. Med. 62, 661 (2013)CrossRefGoogle Scholar
  34. 34.
    I.P. Shvedaite, E.B. Udrenaite, N.A. Lauzhikene, P.G. Gaidyalis, Pharm. Chem. J. 33(6), 313 (1999)CrossRefGoogle Scholar
  35. 35.
    V.K. Jain, B. Jain, U.K. Sharma, D. Saha, Int. J. Pharm. Res. 3(1), 66 (2011)Google Scholar
  36. 36.
    M. Yarim, M. Koksal, I. Durmaz, R. Atalay, Int. J. Mol. Sci. 13, 8071 (2012)CrossRefGoogle Scholar
  37. 37.
    F. Hayat, E. Yoo, H. Rhim, H.Y.P. Choo, Bull. Korean Chem. Soc. 34(2), 495 (2013)CrossRefGoogle Scholar
  38. 38.
    T.H.S. Borrmann, D.C.G. Bertarelli, W. Li, N.C. Florin, A.B. Scheiff, C.E. Muller, J. Med. Chem. 52, 3994 (2009)CrossRefGoogle Scholar
  39. 39.
    Y. Wang, J.B. Petersen, F. Wang, T.J. Kiesow, T.L. Graybill, Z. Yang, J.J. Foley, G.E. Hunsberger, D.B. Schmidt, H.M. Sarau, A.C.S. Elizabeth, L.S. Fisher, M.S. McQueney, K.L. Widdowson, Bioorg. Med. Chem. Lett. 19, 114 (2009)CrossRefGoogle Scholar
  40. 40.
    J. Xiang, Z.K. Wan, H.Q. Li, M. Ipek, E. Binnun, J. Nunez, L. Chen, J.C. McKew, T.S. Mansour, X. Xu, V. Suri, M. Tam, Y. Xing, X. Li, S. Hahm, J. Tobin, E. Saiah, J. Med. Chem. 51, 4068 (2008)CrossRefGoogle Scholar
  41. 41.
    S. Oh, H.I. Moon, I.H. Son, J.C. Jung, Molecules 12, 1125 (2007)CrossRefGoogle Scholar
  42. 42.
    J. Cumming, S. Babu, Y. Huang, C. Carrol, X. Chen, L. Favreau, W. Greenlee, T. Guo, M. Kennedy, K. Reshma, T. Le, G. Li, N. McHugh, P. Orth, L. Ozgur, E. Parker, K. Saionz, A. Stamford, C. Strickland, Bioorg. Med. Chem. Lett. 20, 2837 (2010)CrossRefGoogle Scholar
  43. 43.
    Bruker. APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA (2004)Google Scholar
  44. 44.
    G.M. Sheldrick, Acta Crystallogr. Sect. A71, 3 (2015)CrossRefGoogle Scholar
  45. 45.
    A.L. Spek, Acta. Cryst. A46, C34 (1990)Google Scholar
  46. 46.
    L.J. Farrugia, J. Appl. Cryst. 45, 849 (2012)CrossRefGoogle Scholar
  47. 47.
    C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P.A. Wood, J. Appl. Cryst. 41, 466 (2008)CrossRefGoogle Scholar
  48. 48.
    A.L. Spek, Acta. Cryst. D65, (2009)Google Scholar
  49. 49.
    S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka, M.A. Spackman, Crystal Explorer 3.0, University of Western Australia, Perth, Australia (2001)Google Scholar
  50. 50.
    K.S. Saikat, CrystEngComm 9, 1772 (2013)Google Scholar
  51. 51.
    K.S. Saikat, J. Mol. Structure. 70, 1064 (2014)Google Scholar
  52. 52.
    K. Wingen, J.S. Schwed, K. Isensee, L. Weizel, A. Živković, D. Odazic, H. Stark, Chem. Lett. 24(10), 2236–2239 (2014)CrossRefGoogle Scholar
  53. 53.
    G. Wu, D.H. Robertson, C.L. Brooks III, M. Vieth, J. Comput. Chem. 24, 1549–1562 (2003)CrossRefGoogle Scholar
  54. 54.
    C.A. Lipinski, Revolut. Drug Discov. Today Technol. 1(4), 337–341 (2004)CrossRefGoogle Scholar
  55. 55.
    J.H. Cabral, A.P. Jackson, C.V. Smith, N. Shikotra, A. Maxwell, R.C. Liddington, Nature 388, 903–906 (1997)CrossRefGoogle Scholar
  56. 56.
    J.M. Berger, S.J. Gamblin, S.C. Harrison, J.C. Wang, Nature 379(6562), 225–232 (1996)CrossRefGoogle Scholar
  57. 57.
    S. Sogabe, M. Masubuchi, K. Sakata, T.A. Fukami, K. Morikami, Y. Shiratori, H. Ebiike, K. Kawasaki, Y. Aoki, N. Shimma, A.D. Arcy, F.K. Winkler, D.W. Banner, T. Ohtsuka, Chem. Biol. 9(2), 1119–1128 (2002)CrossRefGoogle Scholar
  58. 58.
    K.K. Prasad, M.P. Toraskar, V.J. Kadam, Mini Rev. Med. Chem. 8, 142–149 (2008)CrossRefGoogle Scholar
  59. 59.
    V. Chandramohan, A. Kaphle, M. Chekuri, S. Gangarudraiah, G. Bychapur Siddaiah, Mini Rev. Med. Chem. 8, 142–149 (2008)CrossRefGoogle Scholar
  60. 60.
    M. Dammalli, V. Chandramohan, Asian Pacific J. Trop. Dis. 4, S635–S640 (1975)CrossRefGoogle Scholar
  61. 61.
    D. Cremer, J.A. Pople, J. Am. Chem. Soc. 97(6), 1354–1358 (1975)CrossRefGoogle Scholar
  62. 62.
    J. Bernstein, R.E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. Int. Ed. Engl. 34, 1555–1573 (1995)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2017

Authors and Affiliations

  • Nivedita Rathnakar Desai
    • 1
  • Krishnaswamy Gurunathan
    • 1
  • Parameshwar Adimule Suchetan
    • 1
  • Aruna Kumar Doyjide Basappa
    • 1
  • Shivalingegowda Naveen
    • 2
  • Neratur Krishnappagowda Lokanath
    • 3
  • Swamy Sreenivasa
    • 1
  1. 1.Department of Studies and Research in ChemistryTumkur UniversityTumkurIndia
  2. 2.Institution of ExcellenceUniversity of MysoreMysoreIndia
  3. 3.Department of Studies in PhysicsUniversity of MysoreMysoreIndia

Personalised recommendations