Issue

Vol. 31 No. 5 (2019): Vol 31 Issue 5

Copyright (c) 2019 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Nickel Oxide-Catalyzed Synthesis of 4-Amino-2H-Chromenes: Its Application in Antimicrobial Studies and Towards Protein Docking

A. Neela
Department of Chemistry, Rani Anna Govt. College for Women, Manonmaniam Sundaranar University, Abishekapatti, Tirunelveli-627012, India
T. Clarina
Department of Chemistry, Sarah Tucker College, Manonmaniam Sundaranar University, Abishekapatti, Tirunelveli-627012, India
https://orcid.org/0000-0003-3082-7562
V. Rama
Department of Chemistry, Sarah Tucker College, Manonmaniam Sundaranar University, Abishekapatti, Tirunelveli-627012, India
https://orcid.org/0000-0001-5384-5865

Corresponding Author(s) : V. Rama

rama242002@gmail.com

Asian Journal of Chemistry, Vol. 31 No. 5 (2019): Vol 31 Issue 5

Abstract

This work involves the synthesis of densely functionalized 2-amino-4H-chromenes by domino Knoevenagel-Michael-cyclization reaction of aromatic aldehydes, β-naphthol and malononitrile in the presence of a catalytic amount of a heterogeneous and reusable green NiO nanoparticle at 50 °C. The biogenic nickel oxide nanoparticles are characterized by Fourier transform infrared radiation, X-ray diffraction analysis, scanning electron microscopy and transmission electron microscopy. The synthesized chromenes are characterized by IR, NMR spectra. The synthesized chromene derivatives are studied for microbial inhibition by Kirby-Bauer disc diffusion method using amikacin and flucanazole as positive control. The compounds are found to have good to moderate antimicrobial activities. Their bio evaluation has been carried out with a protein and identified promising ligands for Mycobacterium tuberculosis InhA through molecular docking.

Keywords

2-Amino-4H-chromenes Knoevenagel-Michael cyclization Antimicrobial activity Molecular docking
Neela, A., Clarina, T., & Rama, V. (2019). Nickel Oxide-Catalyzed Synthesis of 4-Amino-2H-Chromenes: Its Application in Antimicrobial Studies and Towards Protein Docking. Asian Journal of Chemistry, 31(5), 1049–1056. Retrieved from https://asianpubs.org/index.php/ajchem/article/view/247
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. M.M. Khafagy, A.H.F. Abd El-Wahab, F.A. Eid and A.M. El-Agrody, Farmaco, 57, 715 (2002); https://doi.org/10.1016/S0014-827X(02)01263-6.
  2. W.P. Smith, L.S. Sollis, D.P. Howes, C.P. Cherry, D.I. Starkey, N.K.J. Cobley, H. Weston, J. Scicinski, A. Merritt, A. Whittington, P. Wyatt, N. Taylor, D. Green, R. Bethell, S. Madar, R.J. Fenton, P.J. Morley, T. Pateman and A. Beresford, Med. Chem., 41, 787 (1998); https://doi.org/10.1021/jm970374b.
  3. K. Hiramoto, A. Nasuhara, K. Michiloshi, T. Kato and K. Kikugawa, Mutat. Res., 395, 47 (1997); https://doi.org/10.1016/S1383-5718(97)00141-1.
  4. G. Bianchi and A. Tava, Agric. Biol. Chem., 51, 2001 (1987); https://doi.org/10.1080/00021369.1987.10868286.
  5. S.J. Mohr, M.A. Chirigos, F.S. Fuhrman and J.W. Pryor, Cancer Res.,35, 3750 (1975).
  6. D.R. Anderson, S. Hegde, E. Reinhard, L. Gomez, W.F. Vernier, L. Lee, S. Liu, A. Sambandam, P.A. Snider and L. Masih, Bioorg. Med. Chem. Lett., 15, 1587 (2005); https://doi.org/10.1016/j.bmcl.2005.01.067.
  7. F. Eiden and F. Denk, Arch. Pharm., 324, 353 (1991); https://doi.org/10.1002/ardp.19913240606.
  8. S. Makarem, A.A. Mohammadi and A.R. Fakhari, Tetrahedron Lett., 49, 7194 (2008); https://doi.org/10.1016/j.tetlet.2008.10.006.
  9. M. Chen, C. Xie and L. Liu, J. Chem. Eng. Data, 55, 5297 (2010); https://doi.org/10.1021/je100344z.
  10. A.G.A. Elagamay and F.M.A.A. El-Taweel, Indian J. Chem., 29B, 885 (1990).
  11. M.M. Heravi, B. Baghernejad and H.A. Oskooie, J. Chin. Chem. Soc. (Taipei), 55, 659 (2008); https://doi.org/10.1002/jccs.200800098.
  12. M.M. Heravi, K. Bakhtiari, V. Zadsirjan, F.F. Bamoharram and O.M. Heravi, Bioorg. Med. Chem. Lett., 17, 4262 (2007); https://doi.org/10.1016/j.bmcl.2007.05.023.
  13. N.K. Shah, N.M. Shah, M.P. Patel and R.G. Patel, J. Chem. Sci., 125, 525 (2013); https://doi.org/10.1007/s12039-013-0421-y.
  14. L. Chen, X.J. Huang, Y.Q. Li, M.Y. Zhou and W.J. Zheng, Monatsh. Chem., 140, 45 (2009); https://doi.org/10.1007/s00706-008-0008-3.
  15. F.K. Behbahani and S. Maryam, J. Korean Chem. Soc., 57, 357 (2013); https://doi.org/10.5012/jkcs.2013.57.3.357.
  16. Z. Afsaneh, M. Roghieh, S. Maliheh, K. Sussan, S.E. Ardestani and F. Alireza, Iran. J. Pharm. Res., 12, 679 (2013).
  17. H.M. Al-Matar, K.D. Khalil, H. Meier, H. Kolshorn and M.H. Elnagdi, ARKIVOC, 288 (2008); https://doi.org/10.3998/ark.5550190.0009.g27.
  18. B. Baghernejad, M.M. Heravi and H.A. Oskooie, J. Korean Chem. Soc., 53, 631 (2009); https://doi.org/10.5012/jkcs.2009.53.6.631.
  19. S.R. Kolla and Y.R. Lee, Tetrahedron, 67, 8271 (2011); https://doi.org/10.1016/j.tet.2011.08.086.
  20. D. Kumar, V.B. Reddy, B.G. Mishra, R.K. Rana, M.N. Nadagouda and R.S. Varma, Tetrahedron, 63, 3093 (2007); https://doi.org/10.1016/j.tet.2007.02.019.
  21. T.S. Jin, A.Q. Wang, X. Wang, J.S. Zhang and T.S. Li, Synlett, 871 (2004); https://doi.org/10.1055/s-2004-820025.
  22. R.L. Magar, P.B. Thorat, V.B. Jadhav, S.U. Tekale, S.A. Dake, B.R. Patil and R.P. Pawar, J. Mol. Catal. Chem., 374-375, 118 (2013); https://doi.org/10.1016/j.molcata.2013.03.022.
  23. S. Khaksar, A. Rouhollahpour and S.M. Talesh, J. Fluor. Chem., 141, 11 (2012); https://doi.org/10.1016/j.jfluchem.2012.05.014.
  24. M.P. Surpur, S. Kshirsagar and S.D. Samant, Tetrahedron Lett., 50, 719 (2009); https://doi.org/10.1016/j.tetlet.2008.11.114.
  25. D.S. Raghuvanshi and K.N. Singh, ARKIVOC, 305 (2010); https://doi.org/10.3998/ark.5550190.0011.a25.
  26. J.M. Khurana, B. Nand and P. Saluja, Tetrahedron, 66, 5637 (2010); https://doi.org/10.1016/j.tet.2010.05.082.
  27. A.V.B.K. Borhade, B.K. Uphade and D.R. Tope, J. Chem. Sci., 125, 583 (2013); https://doi.org/10.1007/s12039-013-0396-8.
  28. A.A. Harb, A.M. El-Maghraby and S.A. Metwally, Coll. Czech. Chem. Commun., 57, 1570 (1992); https://doi.org/10.1135/cccc19921570.
  29. B. Mahesh and S. Satish, World J. Agric. Sci., 4, 839 (2008).
  30. K. Soo-Hwan, H.S. Lee, D.S. Ryu, S.J. Choi and D.S. Lee, Korean J. Microb. Biotechnol., 39, 77 (2011).
  31. O. Trott and A.J. Olson, J. Comput. Chem., 31, 455 (2010).
  32. H.T. Zhang, J. Ding and G.M. Chow, Mater. Res. Bull., 44, 1195 (2009); https://doi.org/10.1016/j.materresbull.2008.09.042.
  33. B.S. Siddiqui, F. Afshan, Ghiasuddin, S. Faizi, S.N.H. Naqvi and R.M. Tariq, Phytochemistry, 53, 371 (2000); https://doi.org/10.1016/S0031-9422(99)00548-8.
  34. Q. Huang, D. Li, Y. Sun, Y. Lu, X. Su, H. Yang, Y. Wang, W. Wang, N. Shao, J. Hong and C. Chen, Nanotechnology, 18, 105104 (2007); https://doi.org/10.1088/0957-4484/18/10/105104.
  35. J. Parekh and S.V. Chanda, Turk. J. Biol., 31, 53 (2006).
  36. D. Mandal, M.E. Bolander, D. Mukhopadhyay, G. Sarkar and P. Mukherjee, Appl. Microbiol. Biotechnol., 69, 485 (2006); https://doi.org/10.1007/s00253-005-0179-3.
  37. X.-S. Wang, G.-S. Yang and G. Zhao, Tetrahedron, 19, 709 (2008); https://doi.org/10.1016/j.tetasy.2008.02.018.
  38. A.F. Latif, Indian J. Chem., 29B, 664 (1990).
  39. R. Siva Kumar, P. Kumarnallasivan, P.R. Vijai Anand, R. Pradeepchandran, K.N. Jayaveera and R. Venkatnarayanan, Der Pharm. Chem., 2, 100 (2010).
  40. T. Clarina, G.R. Priya Dharsini and V. Rama, Chem. Sci. Trans., 6, 523 (2017); https://doi.org/10.7598/cst2017.1413.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 1