Research Articles

X-ray crystal structure of N'-[(1E)-1-(2,4-dihydroxyphenyl)-ethylidene]pyridine-4-carbohydrazide

1,093 Views358 Downloads1 Citations

PDF

Abstract

Schiff’s base of isonicotinyl hydrazide with 2’,4’-dihydroxy acetophenone (INH-RA) has been designed and synthesized as a part of library enumeration targeting the NS2B-NS3 protease of Dengue virus. Slow evaporation from methanol results in the formation of monoclinic crystals C2/c space group with eight molecules in the unit cell (a=20.0165(3) Å, b=7.7594(10) Å, c=19.4809(3) Å, α=90 °, β=111.368(1) °, γ=90 ° and Z=8).Three dimensional X-ray crystallographic structure of the compound has been determined and refined using SHELXS-97 and SHELXL-2014, respectively to a final R-value of 4.64%

References

  1. Bernstein, J.; Lott, W. A.; Steinberg, B. A.; Yale, H. L. Chemotherapy of experimental tuberculosis. V. Isonicotinic acid hydrazide (nydrazid) and related compounds. American Review of Tuberculosis and Pulmonary Diseases 1952, 65 (4), 357-364.
  2. Offe Hans, A.; Siefken, W.; Domagk, G. Hydrazinderivate und ihre Wirksamkeit gegenüber Mycobacterium tuberculosis. In Zeitschrift für Naturforschung B, 1952; Vol. 7, p 446.
  3. Fox, H. H.; Gibas, J. T. Synthetic Tuberculostats. IV. Pyridine Carboxylic Acid Hydrazides and Benzoic Acid Hydrazides. The Journal of Organic Chemistry 1952, 17 (12), 1653-1660.
  4. https://doi.org/10.1021/jo50012a013
  5. Krishna Murti, C. R. Isonicotinic Acid Hydrazide. In Mechanism of Action of Antimicrobial and Antitumor Agents, Corcoran, J. W.; Hahn, F. E.; Snell, J. F.; Arora, K. L., Eds. Springer Berlin Heidelberg: Berlin, Heidelberg, 1975, 10.1007/978-3-642-46304-4_43pp 623-652.
  6. Hearn, M. J.; Cynamon, M. H. Design and synthesis of antituberculars: preparation and evaluation against Mycobacterium tuberculosis of an isoniazid Schiff base. Journal of Antimicrobial Chemotherapy 2004, 53 (2), 185-191.
  7. https://doi.org/10.1093/jac/dkh041
  8. Thomas, A. B.; Tupe, P. N.; Badhe, R. V.; Nanda, R. K.; Kothapalli, L. P.; Paradkar, O. D.; Sharma, P. A.; Deshpande, A. D. Green route synthesis of Schiff's bases of isonicotinic acid hydrazide. Green Chemistry Letters and Reviews 2009, 2 (1), 23-27.
  9. https://doi.org/10.1080/17518250902922798
  10. Chohan, Z. H.; Arif, M.; Shafiq, Z.; Yaqub, M.; Supuran, C. T. In vitro antibacterial, antifungal & cytotoxic activity of some isonicotinoylhydrazide Schiff's bases and their cobalt (II), copper (II), nickel (II) and zinc (II) complexes. Journal of Enzyme Inhibition and Medicinal Chemistry 2006, 21 (1), 95-103.
  11. https://doi.org/10.1080/14756360500456806
  12. Hearn, M. J.; Cynamon, M. H.; Chen, M. F.; Coppins, R.; Davis, J.; Joo-On Kang, H.; Noble, A.; Tu-Sekine, B.; Terrot, M. S.; Trombino, D.; Thai, M.; Webster, E. R.; Wilson, R. Preparation and antitubercular activities in vitro and in vivo of novel Schiff bases of isoniazid. European Journal of Medicinal Chemistry 2009, 44 (10), 4169-4178.
  13. https://doi.org/10.1016/j.ejmech.2009.05.009
  14. Ferraresi-Curotto, V.; Echeverría, G. A.; Piro, O. E.; Pis-Diez, R.; González-Baró, A. C. Synthesis and characterization of a series of isoniazid hydrazones. Spectroscopic and theoretical study. Journal of Molecular Structure 2017, 1133, 436-447.
  15. https://doi.org/10.1016/j.molstruc.2016.12.018
  16. Aboul-Fadl, T.; Mohammed, F. A.-H.; Hassan, E. A.-S. Synthesis, antitubercular activity and pharmacokinetic studies of some schiff bases derived from 1- alkylisatin and isonicotinic acid hydrazide (inh). Archives of Pharmacal Research 2003, 26 (10), 778-784.
  17. https://doi.org/10.1007/BF02980020
  18. Sheldrick, G. A short history of SHELX. Acta Crystallographica Section A 2008, 64 (1), 112-122.
  19. https://doi.org/10.1107/S0108767307043930
  20. Sheldrick, G. Crystal structure refinement with SHELXL. Acta Crystallographica Section C 2015, 71 (1), 3-8.
  21. https://doi.org/10.1107/S2053229614024218
  22. Bruker, A. APEX2, V2008. 6, SADABS V2008/1, SAINT V7. 60A, SHELXTL V6. 14. Bruker AXS Inc., Madison, Wisconsin, USA: 2008.
  23. Nardelli, M. PARST95 - an update to PARST: a system of Fortran routines for calculating molecular structure parameters from the results of crystal structure analyses. Journal of Applied Crystallography 1995, 28 (5), 659.
  24. https://doi.org/10.1107/S0021889895007138
  25. Nardelli, M. Parst: A system of fortran routines for calculating molecular structure parameters from results of crystal structure analyses. Computers & Chemistry 1983, 7 (3), 95-98.
  26. https://doi.org/10.1016/0097-8485(83)85001-3
  27. Farrugia, L. WinGX and ORTEP for Windows: an update. Journal of Applied Crystallography 2012, 45 (4), 849-854.
  28. https://doi.org/10.1107/S0021889812029111
  29. Spek, A. Structure validation in chemical crystallography. Acta Crystalogr D 2009, 65 (2), 148-155.
  30. https://doi.org/10.1107/S090744490804362X

Author information

Rights and permissions

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

About this article

Cite this article

(1)
Jayaprakash, V.; Timiri, A. K.; Vijayan, V.; Sinha, B. N.; Devadasan, V. X-Ray Crystal Structure of N’-[(1E)-1-(2,4-Dihydroxyphenyl)-ethylidene]pyridine-4-Carbohydrazide. J Pharm Chem 2019, 6 (1). https://doi.org/10.14805/jphchem.2019.art108.
Received
February 22, 2019
Published
March 27, 2019
Section
Research Articles

Versions

Keywords

Most read articles by the same author(s)

1 2 > >>