Abstract
A study of the anti-tuberculosis activity against Mycobacterium tuberculosis ATTC 27294 and an X-ray structural determination of (E)-2-[2-(arylidene)hydrazinyl]pyrimidine, 1, and (E)-N1-(arylidene)pyrimidine-2-carbohydazide, 2, derivatives are presented. The effect of the substituents in the aryl moiety on the antituberculosis (anti-TB) activities of 1 and 2 is compared with that of other heteroaryl hydrazonyl and acylhydrazonyl derivatives. The biological activities of 1 do not depend on the coordinating ability of the substituted aryl group: in 2, the most effective aryl group is 5-nitrofuranyl. The structure determinations of (E)-2-((2-(pyrimidin-2-yl)hydrazono)methyl)-phenol, (E)-N′-(2,5-dihydroxybenzylidene)pyrimidine-2-carbohydrazide and of the hydrate of (E)-N′-(2-hydroxy-4-methylbenzylidene)pyrimidine-2-carbohydrazide, and a literature search of related structures in the CCDC data base, allowed an examination of the more important interactions, including the occurrence of X–Y⋯π interactions.
Acknowledgements
The authors thank the National Crystallographic Service, University of Southampton for the data collection, and for their help and advice.
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: None declared.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Sahu, M., Siddiqui, N. Int. J. Pharm. Pharm. Sci. 2016, 8, 8.Search in Google Scholar
2. Panneer, S. P., Richa, J. C., Vijaysarathy, D. P., Karyn, V. S. Res. Pharm. 2012, 2, 1.Search in Google Scholar
3. Prachayasittikul, S., Pingaew, R., Worachartcheewan, A., Sinthupoom, N., Prachayasittikul, V., Ruchirawat, S., Prachayasittikul, V. Mini-Rev. Med. Chem. 2017, 17, 869. https://doi.org/10.2174/1389557516666160923125801.Search in Google Scholar
4. Liu, X., Feng, T., Wang, D., Liu, H., Yang, C., Li, X., Lin, B., Zhao, Z., Zhou, Y. Tetrahedron Lett. 2016, 57, 4113. https://doi.org/10.1016/j.tetlet.2016.07.100.Search in Google Scholar
5. Tian, C., Wang, M., Han, Z., Fang, F., Zhang, Z., Wang, X., Liu, J. Eur. J. Med. Chem. 2017, 138, 630. https://doi.org/10.1016/j.ejmech.2017.07.002.Search in Google Scholar
6. Gregorić, T., Sedić, M., Grbčić, P., Paravić, A. T., Paveli, S. K., Cetina, M., Vianello, R., Raić-Malić, S. Eur. J. Med. Chem. 2017, 125, 247.10.1016/j.ejmech.2016.11.028Search in Google Scholar PubMed
7. Negi, B., Rawat, D. S. Med. Res. Rev. 2013, 33, 693.10.1002/med.21262Search in Google Scholar PubMed
8. Zuniga, E. S., Korkegian, A., Mullen, S., Hembre, E. J., Ornstein, P. L., Cortez, G., Biswas, K., Kumar, N., Cramer, J., Masquelin, T., Hipskind, P. A., Odingo, J., Parish, T. Bioorg. Med. Chem. 2017, 25, 3922. https://doi.org/10.1016/j.bmc.2017.05.030.Search in Google Scholar
9. Singh, K., Kaur, T. MedChemComm 2016, 7, 749. https://doi.org/10.1039/c6md00084c.Search in Google Scholar
10. Akula, H. K., Kokatla, H., Andrei, G., Snoeck, R., Schols, D., Balzarini, J., Yang, L., Lakshman, M. K. Org. Biomol. Chem. 2017, 15, 1130. https://doi.org/10.1039/c6ob02334g.Search in Google Scholar
11. Anthony, N. G., Baiget, J., Berretta, G., Boyd, M., Breen, D., Edwards, J., Gamble, C., Gray, A. I., Harvey, A. L., Hatziieremia, S., Ho, K. H., Huggan, J. K., Lang, S., Llona-Minguez, S., Luo, J. L., McIntosh, K., Paul, A., Plevin, R. J., Robertson, M. N., Scott, R., Suckling, C. J., Sutcliffe, O. B, Young, L. C., Mackay, S. P. J. Med. Chem. 2017, 60, 7043. https://doi.org/10.1021/acs.jmedchem.7b00484.Search in Google Scholar
12. Sankarganesh, M., Raja, J. D., Sakthikumar, K., Solomon, R. V., Vijayakumar, V. Bioorg. Chem. 2018, 81, 144. https://doi.org/10.1016/j.bioorg.2018.08.006.Search in Google Scholar
13. Atta, K. F. M., Ibrahim, T. M., Farahat, O. O. M., Al-Shargabi, T. Q., Marei, M. G., Bekhit, A. A., El Ashry, E. S. H. Future Med. Chem. 2017, 9, 1913. https://doi.org/10.4155/fmc-2017-0120.Search in Google Scholar
14. Chaturvedi, R. N., Arish, M., Kashif, M., Kumar, V., Reenu, P. K., Rub, A., Malhotra, S. Chem. Select. 2018, 3, 2756. https://doi.org/10.1002/slct.201800056.Search in Google Scholar
15. Wahbeh, J., Milkowski, S. SLAS Technol. 2019, 24, 161. https://doi.org/10.1177/2472630318822713.Search in Google Scholar
16. Guimaraes, D. G., Rolim, L. A., Gonsalves, A. D., Araujo, C. R. M. Rev. Virtual Quim 2017, 9, 2551.10.21577/1984-6835.20170151Search in Google Scholar
17. Verma, G., Marella, A., Shaquiquzzaman, M., Akhtar, M., Ali, M. R., Alam, M. M. J. Pharm. BioAllied Sci. 2014, 6, 69.10.4103/0975-7406.129170Search in Google Scholar PubMed PubMed Central
18. Singh, N., Ranjana, R., Kumari, M., Kumar, B. Int. J. Pharm. Clin. Res. 2016, 8, 162.Search in Google Scholar
19. Rodrigues, F. A. R., Oliveira, A. C. A., Cavalcanti, B. C., Pessoa, C. O., Pinheiro, A. C., de Souza, M V. N. Sci. Pharm. J. 2014, 82, 21. https://doi.org/10.3797/scipharm.1307-25.Search in Google Scholar
20. Bispo, M. L. F., Alcântara, C. C., Moraes, M. O., Pessoa, C. O., Rodrigues, F. A. R., Kaiser, C. R., Wardell, S. M. S. V., Wardell, J. L., de Souza, M. V. N. Monatsh. Chem. 2015, 146, 2041. https://doi.org/10.1007/s00706-015-1570-0.Search in Google Scholar
21. Rodrigues, F. A. R., Bomfim, I. S., Cavalcanti, B. C., Pessoa, C. O., Wardell, J. L., Wardell, S. M. S. V., Pinheiro, A. C., Kaiser, C. R., Nogueira, T. C. M., Low, J. N., Gomes, L. R., de Souza, M. V. N. Bioorg. Med. Chem. Lett 2014, 24, 934. https://doi.org/10.1016/j.bmcl.2013.12.074.Search in Google Scholar
22. Guerreiro, D. D., Lima, L. F., Sá, N. A. R., Mbemya, G. T., Ferreira, A. C. A., Alves, B. G., Maranhao, S. S., Pessoa, C. Ó., Pinheiro, A. C., Nogueira, T. C. M., de Souza, M. V. N., de Figueiredo, J. R., Rodrigues, A. P. R. Res. Vet. Sci. 2020, 128, 261. https://doi.org/10.1016/j.rvsc.2019.12.010.Search in Google Scholar
23. Maranhão, S. S., Moura, A. F., Oliveira, A. C. A., Lima, D. J. B., Barros-Nepomuceno, F. W. A., Paier, C. R. K., Pinheiro, A. C., Nogueira, T. C. M., de Souza, M. V. N., Pessoa, C. Bioorg. Med. Chem. Lett 2020, 30, 126851. https://doi.org/10.1016/j.bmcl.2019.126851.Search in Google Scholar
24. Alves, M. S. D., das Neves, R. N., Sena-Lopes, A., Domingues, M., Casaril, A. M., Segatto, N. V., Nogueira, T. C. M., de Souza, M. V. N., Savegnago, L., Seixas, F. K., Collares, T., Borsuk, S. Parasites Vectors 2020, 13, 59. https://doi.org/10.1186/s13071-020-3923-8.Search in Google Scholar
25. Coimbra, E. S., de Souza, M. V. N., Terror, M. S., Pinheiro, A. C., Granato, J. T. Eur. J. Med. Chem. 2019, 184, 111742. https://doi.org/10.1016/j.ejmech.2019.111742.Search in Google Scholar
26. Coimbra, E. S., Antinarelli, L. M. R., Crispi, M.de A., Nogueira, T. C. M., Pinheiro, A. C., de Souza, M.V.N. ChemMedChem 2018, 13, 1387. https://doi.org/10.1002/cmdc.201800328.Search in Google Scholar
27. Zanatta, N., Amaral, S.S., dos Santos, J. M., de Mello, D. L., Fernandes, L. S., Bonacorso, H. G., Martins, M. A. P., Andricopulo, A. D., Borchhardt, D. M. Bioorg. Med. Chem. 2008, 16, 10236. https://doi.org/10.1016/j.bmc.2008.10.052.Search in Google Scholar
28. Candea, A. L. P., Ferreira, M. L., Pais, K. C., Cardoso, L. N. F., Kaiser, C. R., Henriques, M. G. M. O., Lourenço, M. C., Bezerra, F. A. F. M., de Souza, M. V. N. Bioorg. Med. Chem. Lett. 2009, 19, 6272. https://doi.org/10.1016/j.bmcl.2009.09.098.Search in Google Scholar
29. Lima, C. H. S., Henriques, M. G. M. O., Candea, A. L. P., Lourenço, M. C. S., Bezerra, F. A. F. M., Kaiser, C. R., de Souza, M. V. N. Med. Chem. 2011, 7, 245.10.2174/157340611795564303Search in Google Scholar PubMed
30. Ferreira, M. L., Gonçalves, R. S. B., Cardoso, L. N. F., Kaiser, C. R., Candea, A. L. P., Henriques, M. G. M. O., Lourenço, M. C., Bezerra, F. A. F. M., de Souza, M. V. N. Sci. World J. 2010, 10, 1347. https://doi.org/10.1100/tsw.2010.124.Search in Google Scholar
31. de Souza, M. V. N., Pais, K. C., Kaiser, C. R., Peralta, M. A., Ferreira, M. L., Lourenço, M. C. S. Bioorg. Med. Chem. 2009, 17, 1474. https://doi.org/10.1016/j.bmc.2009.01.013.Search in Google Scholar
32. Vergara, F. M. F., Lima, C. H. S., Henriques, M. G. M. O., Candea, A. L. P., Lourenço, M. C. S., Ferreira, M. L., Kaiser, C. R., de Souza, M. V. N. Eur. J. Med. Chem. 2009, 44, 4954. https://doi.org/10.1016/j.ejmech.2009.08.009.Search in Google Scholar
33. Lourenço, M. C., Ferreira, M. L., de Souza, M. V. N., Peralta, M. A., Vasconcelos, T. R. A., Henriques, M. G. M. O. Eur. J. Med. Chem. 2008, 43, 1344. https://doi.org/10.1016/j.ejmech.2007.08.003.Search in Google Scholar
34. Pinheiro, A. C., de Souza, M. V. N., Lourenco, M. C. S., da Costa, C. F., Baddeley, T. C., Low, J. N., Wardell, S. M. S. V., Wardell, J. L. J. Mol. Struct. 2018, 1178, 655.10.1016/j.molstruc.2018.10.030Search in Google Scholar
35. Nogueira, T. C. M., Cruz, L. D., Lourenco, M. C., de Souza, M. V. N. Lett. Drug. Des. Disc. 2019, 16, 792. https://doi.org/10.2174/1570180815666180627122055.Search in Google Scholar
36. Correira, N. R. L., Noguiera, T. C. M., Pinheiro, A. C., de Souza, M. V. N., Wardell, J. L., Wardell, S. M. S. V. Z. Kristallogr. 2016, 231, 271. https://doi.org/10.1515/zkri-2015-1910.Search in Google Scholar
37. Bispo, M. L. F., de Alcantara, C. C., Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L. Z. Kristallogr. 2015, 230, 519–530.10.1515/zkri-2015-1848Search in Google Scholar
38. de Souza, M. V. N., Noguiera, T. C. M., Wardell, S. M. S. V., Wardell, J. L. Z. Kristallogr. 2014, 229, 587. https://doi.org/10.1515/zkri-2014-1769.Search in Google Scholar
39. Rodrigues, F. A. R., Bomfim, I. S., Cavalcanti, B. C., Pessoa, C. O., Wardell, J. L., Wardell, S. M. S.V., Pinheiro, A. C., Kaiser, C. R., Nogueira, T. C. M., Low, J. N., Gomes, L. R., de Souza, M. V. N. Bioorg. Med. Chem. Lett. 2014, 24, 934. https://doi.org/10.1016/j.bmcl.2013.12.074.Search in Google Scholar
40. Howie, R. A., da Silva Lima, C. H., Kaiser, C. R., de Souza, M. V. N., Wardell, J. L., Wardell, S. M. S. V. Z. Kristallogr. 2010, 225, 158. https://doi.org/10.1524/zkri.2010.1235.Search in Google Scholar
41. Bispo, M. L.F., de Alcantara, C. C., Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L. Z. Kristallogr. 2016, 231, 21.Search in Google Scholar
42. Ravish, I., Raghav, N. Biochem. Anal. Biochem. 2016, 5, 1000253.Search in Google Scholar
43. Kamal, R., Kumar, V., Bhardwaj, V., Kumar, V., Aneja, K. R. Med. Chem. Res. 2015, 24, 2551. https://doi.org/10.1007/s00044-014-1313-5.Search in Google Scholar
44. Kaplancıklı, Z. A., Yurttas, L., Turan-Zitouni, G., Özdemir, A., Göger, G., Demirci, F., Mohsen, U. A. Lett. Drug Des. Disc. 2013, 11, 76.10.2174/15701808113109990037Search in Google Scholar
45. Pape, V. F., Türk, D., Szabó, P., Wiese, M., Enyedy, E. A., Szakács, G. J. Inorg. Biochem. 2015, 144, 18. https://doi.org/10.1016/j.jinorgbio.2014.12.015.Search in Google Scholar
46. Sharma, A., Kumar, V., Khare, R., Gupta, G. K., Beniwal, V. Med. Chem. Res. 2015, 24, 1830. https://doi.org/10.1007/s00044-014-1265-9.Search in Google Scholar
47. Tuberculosis. WHO. 2020, https://www.who.int/news-room/fact-sheets/detail/tuberculosis.Search in Google Scholar
48. Chin, K. L., Sarmiento, M. E., Alvarez-Cabrera, N., Norazmi, M. N., Acosta, A. Eur. J. Clin. Microbiol. Inf. 2020, 19, 799. https://doi.org/10.1007/s10096-019-03771-0.Search in Google Scholar
49. Groom, C. R., Bruno, I. J., Lightfoot, M. P., Ward, S. C. Acta Crystallogr. 2016, B72, 171. https://doi.org/10.1107/s2052520616003954.Search in Google Scholar
50. Franzblau, S. G., Witzig, R. S., McLaughlin, J. C., Torres, P., Madico, G., Hernandez, A., Degnan, M. T., Cook, M. B., Quenzer, V. K., Ferguson, R. M., Gilman, R. H. J. Clin. Microbiol. 1998, 36, 362. https://doi.org/10.1128/jcm.36.2.362-366.1998.Search in Google Scholar
51. Vanitha, J. D., Paramasivan, C. N. Diagn. Microbiol. Infect. Dis. 2004, 49, 179. https://doi.org/10.1016/j.diagmicrobio.2004.04.003.Search in Google Scholar
52. Reis, R. S., Neves, I.Jr., Lourenço, S. L. S., Fonseca, L. S., Lourenço, M. C. S. J. Clin. Microbiol. 2004, 42, 2247. https://doi.org/10.1128/jcm.42.5.2247-2248.2004.Search in Google Scholar
53. CrysAlisPRO (version 1.171.39.9g); Agilent Technologies, Rigaku Oxford Diffraction: Yarnton, Oxfordshire (U.K.), 2015.Search in Google Scholar
54. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112. https://doi.org/10.1107/s0108767307043930.Search in Google Scholar
55. Spek, A. L. Acta Crystallogr. 2009, D65, 148. https://doi.org/10.1107/s090744490804362x.Search in Google Scholar
56. Johnson, C. K., Burnett, M. N. Ortep-III (version 1.0.2), Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Report ORNL-6895, Oak Ridge National Laboratory: Oak Ridge, TN (USA), 1996. Windows version: Farrugia L. J. J. Appl. Crystallogr. 1997, 30, 565.Search in Google Scholar
57. Mercury (version 3.9); Cambridge Crystallographic Data Centre: Cambridge (U. K.), 2019.Search in Google Scholar
58. Shakdofa, M. M. E., Shtaiwi, M. H., Mosy, N., Abdel-Rassel, T. M. A. Main Group Chem. 2014, 13, 187. https://doi.org/10.3233/mgc-140133.Search in Google Scholar
59. Narayana, L. N., Sung-Ok, B. Res. J. Biotech. 2017, 12, 66.Search in Google Scholar
60. Gupta, S., Pal, S., Barik, A. K., Hazra, A., Roy, S., Mandal, T. N., Peng, S.-M., Lee, G.-H., El Fallah, M. S., Tercero, J., Kar, S. K. Polyhedron 2008, 27, 2519. https://doi.org/10.1016/j.poly.2008.05.009.Search in Google Scholar
61. Ray, S., Konar, S., Jana, A., Das, K., Dhara, A., Chatterjee, S., Kar, S. K. J. Mol. Struct. 2014, 1058, 213. https://doi.org/10.1016/j.molstruc.2013.11.004.Search in Google Scholar
62. Vazquez-Garcia, D., Fernandez, A., Lopez-Torres, M., Rodriguez, A., Varela, A., Pereira, M. T., Vila, J. M., Fernandez, J. J. Organometallics 2011, 30, 396.10.1021/om1007902Search in Google Scholar
63. Yuan, J., Liu, M.-J., Liu, C.-M., Kou, H.-Z. Dalton Trans. 2017, 46, 16562. https://doi.org/10.1039/c7dt03233a.Search in Google Scholar
64. Pradhan, R., Banik, M., Cordes, D. B., Slawin, A. M. Z., Saha, N. C. Inorg. Chim. Acta. 2016, 442, 70. https://doi.org/10.1016/j.ica.2015.11.015.Search in Google Scholar
65. Ray, S., Konar, S., Jana, A., Jana, S., Patra, A., Chatterjee, S., Golen, J. A., Rheingold, A. L., Mandal, S. S., Kar, S. K. Polyhedron 2012, 33, 82. https://doi.org/10.1016/j.poly.2011.11.031.Search in Google Scholar
66. Enanga, B., Ariyanayagam, M. R., Stewart, M. L., Barrett, M. P. Antimicrob. Agents Chemother. 2003, 4, 3368. https://doi.org/10.1128/aac.47.10.3368-3370.2003.Search in Google Scholar
67. Hall, B. S., Wilkinson, S. R. Antimicrob. Agents Chemother. 2012, 56, 115. https://doi.org/10.1128/aac.05135-11.Search in Google Scholar
68. Carvalho, S. A., Osorio, L. F. B., Salomao, K., de Castro, S. L., Wardell, S. M. S. V., Wardell, J. L., da Silva, E. F., Fraga, C. A. M. J. Heterocycl. Chem. 2017, 54, 3626. https://doi.org/10.1002/jhet.2989.Search in Google Scholar
69. Cardoso, L. N. F., Bispo, M. L. F., Kaiser, C. R., Wardell, J. L., Wardell, S. M. S. V., Lourenço, M. C. S., Bezerra, F.A. F. M., Soares, R. P. P., Rocha, M. N., de Souza, M. V. N. Arch. Pharm. Chem. Life Sci. 2014, 347, 432. https://doi.org/10.1002/ardp.201300417.Search in Google Scholar
70. Sander, T., Freyss, J., von Korff, M., Rufener, C. J. Chem. Inf. Model. 2015, 55, 460. https://doi.org/10.1021/ci500588j.Search in Google Scholar
71. http://hydra.vcp.monash.edu.au/modules/mod2/bondlen.html.Search in Google Scholar
72. Bernstein, J., Davis, R. E., Shimoni, L., Chang, N.-L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555. https://doi.org/10.1002/anie.199515551.Search in Google Scholar
73. Sankarganesh, M., Raja, J. D., Sakthikumar, K., Solomon, R. V., Rajesh, J., Athimoolam, S., Vijayakumar, V. Bioorg. Chem. 2018, 81, 144. https://doi.org/10.1016/j.bioorg.2018.08.006.Search in Google Scholar
74. Gupta, S., Pal, S., Barik, A. K., Roy, S., Hazra, A., Mandal, T. N., Butcher, R. J., Kar, S. K. Polyhedron 2009, 28, 711. https://doi.org/10.1016/j.poly.2008.12.057.Search in Google Scholar
75. Amaral, S. S., Campos, P.T., dos Santos, J. M., Fernandes, L. S., Martins, M. A. P., Bonacorso, H. G., Zanatta, N. Open Crystallogr. J. 2010, 3, 59. https://doi.org/10.2174/1874846501003010059.Search in Google Scholar
76. Le Fouler, V., Chen, Y., Gandon, V., Bizet, V., Salome, C., Fessard, T., Liu, F., Houk, K. N., Blanchard, N. J. Am. Chem. Soc. 2019, 141, 15901. https://doi.org/10.1021/jacs.9b07037.Search in Google Scholar
77. Shi, J.-T., Gong, Y.-L., Li, J., Wang, Y., Chen, Y., Ding, S., Liu, J. Chin. J. Struct. Chem. 2019, 38, 1530.Search in Google Scholar
78. Gu, W., Wu, R., Qi, S., Gu, C., Si, F., Chen, Z. Molecules 2012, 17, 4634. https://doi.org/10.3390/molecules17044634.Search in Google Scholar
79. Pejov, L. Chem. Phys. Lett. 2001, 339, 269. https://doi.org/10.1016/s0009-2614(01)00341-4.Search in Google Scholar
80. Geng, Y., Takatani, T., Hohenstein, E. G., Sherrill, C. D. J. Phys. Chem. A 2010, 114, 3576. https://doi.org/10.1021/jp9099495.Search in Google Scholar
81. Gosling, M. P., Pugliesi, I., Cockett, M. C. R. Phys. Chem. Chem. Phys. 2010, 12, 132. https://doi.org/10.1039/b916815j.Search in Google Scholar
82. Fun, H.-K., Loh, W.-S., Nayak, S. P. Acta Crystallogr. 2010, E66, o2467. https://doi.org/10.1107/s1600536810033283.Search in Google Scholar
83. Dhara, A., Guchhait, N., Bhattacharya, S. C. J. Ind. Chem. Soc. 2017, 94, 781.Search in Google Scholar
84. Lukov, V. V., Tsaturyan, A. A., Tupolova, Y. P., Levchenkov, S. I., Vlasenko, V. G., Popov, L. D., Pankov, I. V., Poler, J. C. CCDC 1845762: Experimental Crystal Structure Determination, 2019; https://doi.org/10.5517/ccdc.csd.cc1zynq9.Search in Google Scholar
85. Jiang, N., Zuo, J., Wang, H., Han, M., Zhai, X. Acta Crystallogr. 2012, E68, o1557. https://doi.org/10.1107/s1600536812018272.Search in Google Scholar
86. Sarel, S., Avramovici-Grisaru, S., Cohen, S. Heterocycles 1998, 49, 393. https://doi.org/10.3987/com-98-s51.Search in Google Scholar
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