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Vol. 31 No. 9 (2019): Vol 31 Issue 9

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Design and Synthesis of Bis-pyrimidines Linked with Thiazolidin-4-one as New Antibacterial Agents

https://doi.org/10.14233/ajchem.2019.22002
Ch. Sanjeeva Reddy
Department of Chemistry, Kakatiya University, Warangal-506009, India
A. Nagaraj
Department of Chemistry, Telangana University, Nizamabad-503322, India
V. Yakub
Department of Chemistry, Kakatiya University, Warangal-506009, India
B. Kalyani
Department of Chemistry, Kakatiya University, Warangal-506009, India

Corresponding Author(s) : Ch. Sanjeeva Reddy

chsrkuc@yahoo.co.in

Asian Journal of Chemistry, Vol. 31 No. 9 (2019): Vol 31 Issue 9

Abstract

A series of novel 3-4-[2-hydroxy-5-(4-hydroxy-3-2-[2-(aryl)-4-oxo-1,3-thiazolan-3-yl]-6-phenyl-4-pyrimidinylbenzyl)phenyl]-6-phenyl-2-pyrimidinyl-2-(aryl)-1,3-thiazolan-4-ones 5(a-j) have been synthesized and assayed for their antibacterial activity against B. subtilis, B. sphaericus, S. aureus, P. aeruginosa, K. Aerogenes and C. violaceum. The inhibition zones and minimal inhibitory concentrations were measured and compared with the streptomycin. The antibacterial screening data reveal that the compounds containing 4-nitrophenyl (5c), 3-nitrophenyl (5d), 4-dimethylaminophenyl (5g) and 1,3-benzodioxole (5j) moiety at 2-position of the thiazolidin-4-one ring exhibited potent inhibitory activity towards all the tested microorganism, which is higher than streptomycin. The other compounds also showed moderate to good activity.

Keywords

Bis-heterocycles Thiazolidin-4-one Pyrimidine Antibacterial activity
Reddy, C. S., Nagaraj, A., Yakub, V., & Kalyani, B. (2019). Design and Synthesis of Bis-pyrimidines Linked with Thiazolidin-4-one as New Antibacterial Agents. Asian Journal of Chemistry, 31(9), 1913–1918. https://doi.org/10.14233/ajchem.2019.22002
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References
  1. A.T. Balaban, D.C. Oniciu and A.R. Katritzky, Chem. Rev., 104, 2777 (2004); https://doi.org/10.1021/cr0306790.
  2. M. García-Valverde and T. Torroba, Molecules, 10, 318 (2005); https://doi.org/10.3390/10020318.
  3. M. Kvasnica, M. Urban, N.J. Dickinson and J. Sarek, Nat. Prod. Rep., 32, 1303 (2015); https://doi.org/10.1039/C5NP00015G.
  4. S.A. Ahmed, S. Odde, P.R. Daga, J.J. Bowling, M.K. Mesbah, D.T. Youssef, S.I. Khalifa, R.J. Doerksen and M.T. Hamann, Org. Lett., 9, 4773 (2007); https://doi.org/10.1021/ol7020675.
  5. M.V.N. De Souza, J. Sulfur Chem., 26, 429 (2005); https://doi.org/10.1080/17415990500322792.
  6. R. Bentley, J. Chem. Educ., 81, 1462 (2004); https://doi.org/10.1021/ed081p1462.
  7. M.A. Ciufolini and D. Lefranc, Nat. Prod. Rep., 27, 330 (2010); https://doi.org/10.1039/b919071f.
  8. N. Ghazzi, J.E. Perez, T.K. Antonucci, J.H. Driscoll, S.M. Huang, B.W. Faja and R.W. Whitcomb, Diabetes, 46, 433 (1997); https://doi.org/10.2337/diab.46.3.433.
  9. U. Schmidt, R. Utz, A. Lieberknecht, H. Griesser, B. Potzolli, J. Bahr, K. Wagner and P. Fischer, Synthesis, 233 (1987); https://doi.org/10.1055/s-1987-27899.
  10. D. Kaminskyy, A. Kryshchyshyn and R. Lesyk, Eur. J. Med. Chem., 140, 542 (2017); https://doi.org/10.1016/j.ejmech.2017.09.031.
  11. N. Ergenc, G. Capan, N.S. Gunay, S. Ozkirimli, M. Gungor, S. Ozbey and E. Kendi, Arch. Pharm., 332, 343 (1999); https://doi.org/10.1002/(SICI)1521-4184(199910)332:10<343::AIDARDP343>3.0.CO;2-0.
  12. K.R.A. Abdellatif, M.A. Abdelgawad, H.A.H. Elshemy and S.S.R. Alsayed, Bioorg. Chem., 64, 1 (2016); https://doi.org/10.1016/j.bioorg.2015.11.001.
  13. N.B. Patel and F.M. Shaikh, Saudi Pharm. J., 18, 129 (2010); https://doi.org/10.1016/j.jsps.2010.05.002.
  14. N.B. Patel and M.D. Patel, Med. Chem. Res., 26, 1772 (2017); https://doi.org/10.1007/s00044-017-1837-6.
  15. U.G. Cihan, D. Satana, G. Ozhan and G. Capan, J. Enzyme Inhib. Med. Chem., 31, 369 (2016); https://doi.org/10.3109/14756366.2015.1024673.
  16. M. Faizi, R. Jahani, S.A. Ebadi, S.A. Tabatabai, E. Rezaee, M. Lotfaliei, M. Amini and A. Almasirad, EXCLI J., 16, 52 (2017); https://doi.org/10.17179/excli2016-692.
  17. P.N. Bhargava and M.R. Chaurasia, J. Pharm. Sci., 58, 896 (1969); https://doi.org/10.1002/jps.2600580728.
  18. A.R. Surrey, J. Am. Chem. Soc., 71, 3354 (1949); https://doi.org/10.1021/ja01178a023.
  19. H.D. Troutman and L.M. Long, J. Am. Chem. Soc., 70, 3436 (1948); https://doi.org/10.1021/ja01190a064.
  20. R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouque and E. De Clercq, Bioorg. Med. Chem., 15, 1725 (2007); https://doi.org/10.1016/j.bmc.2006.12.003.
  21. V. Ravichandran, B.R. Prashantha Kumar, S. Sankar and R.K. Agrawal, Eur. J. Med. Chem., 44, 1180 (2009); https://doi.org/10.1016/j.ejmech.2008.05.036.
  22. N.J. Hrib, J.G. Jurcak, D.E. Bregna, R.W. Dunn, H.M. Geyer, H.B. Hartman, J.E. Roehr, K.L. Rogers and D.K. Rush, J. Med. Chem., 35, 2712 (1992); https://doi.org/10.1021/jm00092a024.
  23. R. Lesyk and B. Zimenkovsky, Curr. Org. Chem., 8, 1547 (2004); https://doi.org/10.2174/1385272043369773.
  24. Y. Tanabe, H. Yamamoto, M. Murakami, K. Yanagi, Y. Kubota, H. Okumura, Y. Sanemitsu and G. Suzukamo, J. Chem. Soc. Perkin Trans I, 7, 935 (1995); https://doi.org/10.1039/p19950000935.
  25. V. Sharma, N. Chitranshi and A.K. Agarwal, Int. J. Med. Chem., 2014, Article ID 202784 (2014) https://doi.org/10.1155/2014/202784.
  26. R.A. Gupta and S.G. Kaskhedikar, Med. Chem. Res., 22, 3863 (2013); https://doi.org/10.1007/s00044-012-0385-3.
  27. K.S. Atwal, G.C. Rovnyak, S.D. Kimball, D.M. Floyd, S. Moreland, B.N. Swanson, J.Z. Gougoutas, J. Schwartz, K.M. Smillie and M.F. Malley, J. Med. Chem., 33, 2629 (1990); https://doi.org/10.1021/jm00171a044.
  28. C. Mallikarjunaswamy, L. Mallesha, D.G. Bhadregowda and O. Pinto, Arab. J. Chem., 10, S484 (2017); https://doi.org/10.1016/j.arabjc.2012.10.008.
  29. F. Xie, H. Zhao, L. Zhao, L. Lou and Y. Hu, Bioorg. Med. Chem. Lett., 19, 275 (2009); https://doi.org/10.1016/j.bmcl.2008.09.067.
  30. C.K. Chu, J.W. Beach, G.V. Ullas and Y. Kosugi, Tetrahedron Lett., 29, 5349 (1988); https://doi.org/10.1016/S0040-4039(00)82864-6.
  31. J.W.M. van der Meer, Front. Public Health, 1, 7 (2013); https://doi.org/10.3389/fpubh.2013.00007.
  32. D.M. Morens and A.S. Fauci, PLoS Pathog., 9, e1003467 (2013); https://doi.org/10.1371/journal.ppat.1003467.
  33. J. Davies and D. Davies, Microbiol. Mol. Biol. Rev., 74, 417 (2010); https://doi.org/10.1128/MMBR.00016-10.
  34. D. Jasovsky, J. Littmann, A. Zorzet and O. Cars, Ups. J. Med. Sci., 121, 159 (2016); https://doi.org/10.1080/03009734.2016.1195900.
  35. N. Alsaad, B. Wilffert, R. van Altena, W.C.M. de Lange, T.S. van der Werf, J.G.W. Kosterink and J.-W.C. Alffenaar, Eur. Respir. J., 43, 884 (2014); https://doi.org/10.1183/09031936.00113713.
  36. Y.N. Mabkhot, A. Barakat, A.M. Al-Majid and S.A. Alshahrani, Int. J. Mol. Sci., 13, 2263 (2012); https://doi.org/10.3390/ijms13022263.
  37. T. Voloshchuk, N.S. Farina, O.R. Wauchope, M. Kiprowska, P. Haberfield and A. Greer, J. Nat. Prod., 67, 1141 (2004); https://doi.org/10.1021/np049899e.
  38. F. Celik, Y. Unver, B. Barut, A. Ozel and K. Sancak, Med. Chem., 14, 230 (2018); https://doi.org/10.2174/1573406413666171120165226.
  39. A. Srinivas, A. Nagaraj and C.S. Reddy, Eur. J. Med. Chem., 45, 2353 (2010); https://doi.org/10.1016/j.ejmech.2010.02.014.
  40. Ch. Sanjeeva Reddy, D. Chandrashekar Rao, V. Yakub and A. Nagaraj, Chem. Pharm. Bull. (Tokyo), 58, 1328 (2010); https://doi.org/10.1248/cpb.58.1328.
  41. Ch. Sanjeeva Reddy, M. Vani Devi, G.R. Kumar, M. Sunitha and A. Nagaraj, J. Heterocycl. Chem., 50, 557 (2013); https://doi.org/10.1002/jhet.1528.
  42. C.S. Marvel and N. Tarkoy, J. Am. Chem. Soc., 79, 6000 (1957); https://doi.org/10.1021/ja01579a041.
  43. A. Nagaraj and C.S. Reddy, J. Heterocycl. Chem., 44, 1181 (2007); https://doi.org/10.1002/jhet.5570440534.
  44. A. Nagaraj and Ch. Sanjeeva Reddy, J. Iran. Chem. Soc., 5, 262 (2008); https://doi.org/10.1007/BF03246116.
  45. J.H. Jorgensen, Infect. Dis. Clin. North Am., 7, 393 (1993)
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