Schiff base of isoniazid and ketoprofen: synthesis, X-ray crystallographic, spectroscopic, antioxidant, and computational studies
Schiff base of isoniazid and ketoprofen: synthesis, X-ray crystallographic, spectroscopic, antioxidant, and computational studies
Ketoprofen and isoniazid together are a potential combination of a nonsteroidal antiinflammatory drugand an antitubercular medicine to treat tuberculosis and associated symptoms like fever and fatigue. The Schiff baseof isoniazid with ketoprofen is synthesized in this research. Infrared spectroscopy (IR) and X-ray diffraction (XRD)analysis of the crystal packing proved the formation of the Schiff base and the existence of N-H· · ·O hydrogen bondsbetween the hydrogen-bonded dimer of the Schiff base. The complete geometrical optimization of the monomer andhydrogen-bonded dimer of the Schiff base is performed utilizing M06-2X/6-31G(d,p) level theory and compared withthe experimental data to optimize the molecular structure. The effect of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicalscavenging activity shows that the synthesized Schiff base has improved antioxidant activity. Molecular docking studiesagainst Mycobacterium tuberculosis (Mtb) RNA polymerase-related targets with PDB codes 2M6O and 4KBJ and lungsurfactant protein A (SP-A) with PDB ID 5FFT suggest that it can be screened as a potent drug against Mtb infectionof the lungs. Frontier orbital theory analysis shows a high energy gap between the HOMO and LUMO, which suggeststhat the reported Schiff base might be a bioactive compound. Different experimental (XRD, IR, thermal gravimetricanalysis, differential scanning calorimetry) and computational studies correlate and validate findings related to this novelSchiff base.
___
- 1. Kwiatkowska, S.; Piasecka, G.; Zieba, M.; Piotrowski, W.; Nowak, D. Respir. Med. 1999, 93, 272-276.
- 2. Walubo, A.; Smith, P. J.; Folb, P. I. Biomed. Environ. Sci. 1995, 8, 106-113.
- 3. Strausz, J.; Muller-Quernheim, J.; Steppling, H.; Nagel, M.; Ferlinz, R. Pub. Med. 1990, 44, 222-223.
- 4. Charles, M. H.; Simon, J. G.; John, H. Int. J. Pharm. 2003, 261,165-169.
- 5. Yalcin, T.; Gulgun, Y.; Umit, G. Farmaco 1999, 54, 648-652.
- 6. Jachowicz, R.; Nurnberg, E.; Pieszczek, B. Int. J. Pharm. 2000, 206, 13-21.
- 7. Lagrange, F.; P´enhourcq, F.; Matoga, M.; Bannwarth, B. J. Pharm. Biomed. Anal. 2000, 23, 793-802.
- 8. Tettey-Amlalo, R. N. O.; Kanfer, I. J. Pharm. Biomed. Anal. 2009, 50, 580-586.
- 9. Vergote, G. J.; Vervaet, C.; Driessche, I. V. Int. J. Pharm. 2001, 219, 81-87.
- 10. Makiko, F.; Naohide, H.; Kumi, S. Int. J. Pharm. 2000, 20, 117-125.
- 11. Schultheiss, N.; Newman, A. Cryst. Growth Des. 2009, 9, 2950-2967.
- 12. Jones, W. D. S.; Motherwell, A. V. MRS Bull. 2006, 31, 875-879.
- 13. Almarsson, O.; Zaworotko, M. J. Chem. Commun. 2004, 17, 1889-1896.
- 14. Mashhadi, S. M. A.; Yunus, U.; Bhatti, M. H.; Tahir, M. N. J. Mol. Struc. 2014, 1076, 446-452.
- 15. Mashhadi, S. M. A.; Yunus, U.; Bhatti, M. H.; Ahmad, I.; Tahir, M. N. J. Mol. Struc. 2016, 1117, 17-21.
- 16. Sathe, B. S.; Jaychandran, E.; Jagtap, V. A.; Sreenivasa, Int. J. Pharm. Res. Dev. 2011, 3, 164-169.
- 17. Sondhi, S. M.; Singh, N.; Kumar, A.; Lozach, O.; Meijer, L. Bioorg. Med. Chem. 2006, 14, 3758-3765.
- 18. Pandey, A.; Dewangan, D.; Verma, S.; Mishra, A.; Dubey, R. D. Int. J. Chem. Tech. Res. 2011, 3, 178-184.
- 19. Chinnasamy, R. P.; Sundararajan, R.; Govindaraj, S. J. Adv. Pharm. Tech. Res. 2010, 1, 342-347.
- 20. Wei, D.; Li, N.; Lu, G.; Yao, K. Science in China B 2006, 49, 225-229.
- 21. Sidwell, R. W.; Huffman, J. H.; Khare, G. P.; Allen, L. B.; Witkowski, J. T.; Robins, R. K. Science 1972, 177, 705-706.
- 22. Witkowski, J. T.; Robins, R. K.; Khare, G. P.; Sidwell, R. W. J. Med. Chem. 1973, 16, 935-937.
- 23. Clemons, M.; Coleman, R. E.; Verma, S. Cancer Treat. Rev. 2004, 30, 325-332.
- 24. Budavari, S. The Merck Index ; Merck: Whitehouse Station, NJ, USA, 1996.
- 25. Haber, J. J. Czech Phys. 2001, 140, 596-604.
- 26. Walczak, K.; Gondela, A.; Suwi´nski, J. Eur. J. Med. Chem. 2004, 39, 849-853.
- 27. Holla, B. S.; Poojary, K. N.; Rao, B. S. Eur. J. Med. Chem. 2002, 37, 511-517.
- 28. Holla, B. S.; Veerendra, B.; Shivananda, M. K. Eur. J. Med. Chem. 2003, 38, 759-767.
- 29. Amir, M.; Shikha, K. Eur. J. Med. Chem. 2004, 39, 535-545.
- 30. Almasirad, A.; Tabatabai, S. A.; Faizi, M. Bioorg. Med. Chem. Lett. 2004, 14, 6057-6059.
- 31. Tarafder, M. T. H.; Kasbollah, A.; Saravanan, N. J. Biochem. Mol. Biol. Biophys. 2002, 6, 85-91.
- 32. Vicini, P.; Geronikaki, A.; Incerti, M. Bioorg. Med. Chem. 2003, 11, 4785-4789.
- 33. Bekircan, O.; Kahveci, B.; K¨u¸c¨uk, M. Turk. J. Chem. 2006, 30, 29-40.
- 34. Sanner, M. F. J. Mol. Graphics Mod. 1999, 17, 57-61.
- 35. Kumar, G. S. S.; Kumaresan, S.; Muthu Prabu, A. A.; Seethalakshmi, P. G. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2013, A-101, 244-263.
- 36. Tahir, M. N.; Khalid, M.; Islam, A.; Mashhadi, S. M. A.; Braga, A. A. C. J. Mol. Struct. 2017, 1127, 766-776.
- 37. Naseem, S.; Khalid, M.; Tahir, M. N.; Halim, M. A.; Braga, A. A. C.; Naseer, M. M.; Shafiq, Z. J. Mol. Struct. 2017, 1143, 235-244.
- 38. Arshad, M. N.; Al-Dies, A. M.; Asiri, A. M.; Khalid, M.; Birinji, A. S.; Al-Amry, K. A.; Braga, A. A. C. J. Mol. Struct. 2017, 1141, 142-156.
- 39. Sumrra, S. H.; Mushtaq, F.; Khalid, M.; Raza, M. A.; Nazar, M. F.; Ali, B.; Braga, A. A. C. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2018, 190, 197-207.
- 40. Sheela, N. R.; Muthu, S.; Sampathkrishnan, S. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014, 120, 237-251.
- 41. Hoque, M. M.; Halim, M. A.; Rahman, M. M.; Hossain, M. I.; Khan, M. W. J. Mol. Struct. 2013, 1054, 367-374.
- 42. Adeel, M.; Braga, A. A. C.; Tahir, M. N.; Haq, F.; Khalid, M.; Halim, M. A. J. Mol. Struct. 2017, 1131, 136-148.
- 43. Demircioglu, z.; Albayrak, C.; Buyukgungor. O. J. Mol. Struct. 2014, 1065, 210-222.
- 44. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
- 45. Stallings, C. L.; Stephanou, N. C.; Chu, L.; Hochschild, A.; Nickels, B. E. Cell 2009, 138, 146-159.
- 46. Frisch, M. J.; Nielsen, A. B.; Holder, A. J. GaussView User’s Manual; Gaussian Inc.: Pittsburgh, PA, USA, 2000.
- 47. Salazar, A. T.; Doughty, B. L. P.; Lewis, R. A.; Ghosh, S.; Parsy, M.; Simpson, P. J.; Dwyer, K. O.; Matthews, S. J.; Paget, M. S. Nucleic Acids Res. 2013, 41, 5679-5691.
- 48. Bekircan, O.; Bektas, H. Molecules 2008, 13, 2126-2135.
- 49. Kahveci, B.; Bekircan, O.; Karaoglu, S¸. A. Ind. J. Chem. 2005, 44, 2614-2617.
- 50. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. et al. Gaussian 09, Revision D.01 ; Gaussian, Inc.: Wallingford, CT, USA, 2009.
- 51. Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, 864-871.
- 52. Hanwell, M. D.; Curtis, D. E.; Lonie, D. C.; Vandermeersch, T.; Zurek, E.; Hutchison, G. R. J. Cheminform. 2012, 4, 1-17.
- 53. Goh, B. C.; Wu, H.; Rynkiewicz, V.; Schulten, K.; Seaton, B. A.; McCormack, F. X. Biochemistry 2016, 55, 3692-3701.