Skip to main navigation menu Skip to main content Skip to site footer
##common.pageHeaderLogo.altText##

Articles

Vol. 1 No. 1 (2010): January-March 2010

Synthesis, Anti-Tuberculosis and Antiviral Activity of Novel 2-isonicotinoylhydrazono-5-arylidene-4-thiazolidinones

DOI
https://doi.org/10.37285/ijddd.1.1.3
Submitted
November 18, 2024
Published
2010-02-15

Abstract

This paper describes the synthesis and structural elucidation of some novel N'-[5-(substituted benzylidene)-3-alkyl-4-oxo-1,3-thiazolidin-2-ylidene]isonicotinohydrazides and evaluation of their chemotherapeutic potency. The most potent derivative demonstrated an IC90 value of 2.039 µg/ml and an IC50 value of 1.267 µg/ml against M. Tuberculosis H37Rv while one of our compounds inhibited cytopathicity of HIV-1 (IIIB) by 50% at 8.73 µg/ml and other two derivatives were found active against either thymidine kinase positive or deficient strains of varicella-zoster virus with IC50 values of 2.0 and 1.8 µg/ml.

References

  1. 1. Clarck, C.; Jacobs M.; Appelbaum P. J. Clin. Microbiol. 1998, 36, 3759.
  2. 2. Davidson, P.T.; Le, H.Q. Drugs 1992, 43, 651.
  3. 3. Snider, D.E.Jr.; Raviglione, M.; Kochi, A. In Tuberculosis : Pathogenesis, Protection and Control; Bloom, B., Ed.; ASM : Washington, D.C., 1994; pp 3-11.
  4. 4. WHO Website. Links for an overview of tuberculosis worldwide, <http://www.who.int/tb/en >
  5. 5. The Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) Website, <http://taacf.org/about-TB-background.htm >
  6. 6. Sah, P.P.T.; Peoples, S.A. J. Am. Pharm. Assoc. 1954, 43, 513.
  7. 7. Cocco, M.T.; Congiu, C.; Onnis, V.; Pusceddo, M.C.; Schivo, M.L.; De Logu, A. Eur. J. Med. Chem. 1999, 34, 1071.
  8. 8. Sriram, D.; Yogeeswari, P.; Madhu, K. Bioorg. Med. Chem. Lett. 2005, 15, 4502.
  9. 9. Shindikar, A.V.; Viswanathan, C.L.; Bioorg. Med. Chem Lett. 2005, 15, 1803.
  10. 10. Imramovský, A.; Polanc, S.; Vinšová, J.; Kočevar, M.; Jampílek, J.; Rečková, Z.; Kaustová, J. Bioorg. Med. Chem. 2007, 15, 2551.
  11. 11. Janin, Y.L. Bioorg. Med. Chem. 2007, 15, 2479.
  12. 12. Maccari, R.; Ottanà, R.; Vigorita, M.G. Bioorg. Med. Chem. Lett. 2005, 15, 2509.
  13. 13. Sinha, N.; Jain, S.; Tilekar, A.; Upadhayaya, R.S.; Kishore, N.; Jana, G.H.; Arora, S.K. Bioorg. Med. Chem.Lett. 2005, 15, 1573.
  14. 14. Maccari, R.; Ottanà, R.; Bottari, B.; Rotondo, E.; Vigorita, M.G. Bioorg. Med. Chem.Lett. 2004, 14, 5731.
  15. 15. Fu, L.M.; Shinnick, T.M. Tuberculosis 2007, 87, 63.
  16. 16. Andres, C.J.; Bronson, J.J.; D’Andrea, S.V.; Deshpande,
  17. M. S.; Falk, P.J.; Grant-Young, K.A.; Harte, W.E.; Ho, H.; Misco, P.F.; Robertson, J.G.; Stock, D.; Sun, Y.; Walsh, A.W. Bioorg. Med. Chem. Lett. 2000, 10, 715.
  18. 17. Bonde, C.G.; Gaikwad, N.J. Bioorg. Med. Chem. 2004, 12, 2151.
  19. 18. Küçükgüzel, Ş.G.; Oruç, E.E.; Rollas, S.; Şahin, F.; Özbek, A. Eur. J. Med. Chem. 2002, 37, 197.
  20. 19. Barreca, M.L.; Chimirri, A.; Luca, L.D.; Monforte, A.M.; Monforte, P.; Rao, A.; Zappalà, M.; Balzarini, J.; De Clercq, E.; Pannecouque, C.; Witvrouw, M. Bioorg. Med. Chem. Lett. 2001, 11, 1793.
  21. 20. Rao, A.; Carbone, A.; Chimirri, A.; De Clercq, E.; Monforte, A.M.; Monforte, P.; Pannecouque, C.; Zappalà,
  22. M. Il Farmaco 2002, 57, 747.
  23. 21. Rao, A.; Carbone, A.; Chimirri, A.; De Clercq, E.; Monforte, AM.; Monforte, P.; Pannecouque, C.; Zappalà,
  24. M. Il Farmaco 2003, 58, 115.
  25. 22. Barreca, M.L.; Chimirri, A.; De Clercq, E; Luca, L.D.; Monforte, A.M.; Monforte, P.; Rao, A.; Zappalà, M. Il Farmaco 2003, 58, 259.
  26. 23. Ottanà, R.; Carotti, S.; Maccari, R.; Landini, I.; Chiricosta, G.; Caciagli, B.; Vigorita, M.G.; Mini, E. Bioorg. Med. Chem. Lett. 2005, 15, 3930.
  27. 24. Babaoglu, K.; Page, M.A.; Jones, V.C.; McNeil, M.R.; Dong, C.; Naismith, J.H.; Lee, R.E. Bioorg. Med. Chem. Lett. 2003, 13, 3227.
  28. 25. Rao, A.; Balzarini, J.; Carbone, A.; Chimirri, A.; De Clercq, E.; Monforte, A.M.; Monforte, P.; Pannecouque, C.; Zappalà, M. Il Farmaco 2004, 59, 33.
  29. 26. Balzarini, J.; Orzeszko, B.; Maurin, J.K.; Orzeszko, A. Eur. J. Med. Chem. 2007, 42, 993.
  30. 27. Ding, Y.; Smith, K.L.; Varaprasad, C.V.; Chang, E.; Alexander, J.; Yao, N. Bioorg. Med. Chem. Lett. 2007, 17, 841.
  31. 28. Yan, S.; Larson, G.; Wu, J.Z.; Appleby, T.; Ding, Y.; Hamatake, R.; Hong, Z.; Yao, N. Bioorg. Med. Chem. Lett. 2007, 17, 63.
  32. 29. Lee, G.; Piper, D.E.; Wang, Z.; Anzola, J.; Powers, J.; Walker, N.; Li, Y. J. Mol. Biol. 2006, 357, 1051.
  33. 30. Küçükgüzel, Ş.G.; Kocatepe, A.; De Clercq, E.; Şahin, F.; Güllüce, M. Eur. J. Med. Chem. 2006, 41, 353.
  34. 31. Kaushik-Basu, N.; Bopda-Waffo, A.; Basu, A.; Chen, Y.; Talele, T.T.; Küçükgüzel, Ş.G. Frontiers in Bioscience 2008, 13, 3857.
  35. 32. Gududuru, V.; Hurh, E.; Dalton, J.T.; Miller, D.D. Bioorg. Med. Chem. Lett. 2004, 14, 5289.
  36. 33. Snider, D.E. Tubercle 1980, 61, 191.
  37. 34. Gülerman, N.N.; Doğan, H.N.; Rollas, S.; Johansson, C.; Çelik, C. Il Farmaco 2001, 56, 953.
  38. 35. Cardia, M.C.; Distinto, S.; Macchioni, E.; Plumitallo, A.; Saddi, M.; Sana, M.L.; DeLogu, A. J. Heterocyclic Chem. 2006, 43, 1337.
  39. 36. Tatar, E.; Küçükgüzel, İ.; De Clercq, E.; Şahin, F.; Güllüce, M. Arkivoc 2008, xiv, 191.
  40. 37. Tozkoparan, B.; Akgün, H.; Ertan, M.; Rübsamen, K. Arch. Pharm. (Weinheim) 1995, 328, 169.
  41. 38. Chaouni-Benabdallah, A.; Galtier,C.; Allouchi, H.; Kherbeche, A.; Chavignon, O.; Teulade, J.C.; Witvrouw, M.; Pannecouque, C.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E.; Fauvelle, F.; Enguehard, C.; Gueiffier, A. Chem. Pharm. Bull. 2001, 12, 1631.
  42. 39. Tetko, I.V.; Gasteiger, J.; Todeschini, R.; Mauri, A.; Livingstone, D.; Ertl, P.; Palyulin, V.A.; Radchenko,
  43. E. V.; Zefirov, N.S.; Makarenko, A.S.; Tanchuk, V.Y.; Prokopenko, V.V. J. Comput. Aid. Mol. Des. 2005, 19, 453.
  44. 40. VCCLAB, Virtual Computational Chemistry Laboratory, 2005, <http://www.vcclab.or g>.
  45. 41. Collins, L.; Franzblau,S.G.;Antimicrob.Agents.Chemother. 1997, 41, 1004.
  46. 42. De Clercq, E.; Descamps, J.; Verhelst,G.; Walker, R.T.; Jones, A.S.; Torrence, P.F.; Shugar, D. J. Infect. Dis. 1980, 141, 563.
  47. 43. De Clercq, E.; Holý, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P.C. Nature 1986, 323, 464.
  48. 44. De Clercq, E. Antimicrob. Agents Chemother. 1985, 28, 84.
  49. 45. Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P. J. Virol. Methods 1988, 20, 309.
  50. 46. Popovic, M.; Sarngadharan, M.G.; Read, E.; Gallo, R.C. Science 1984, 224, 497.
  51. 47. Barré-Sinoussi, F.; Chermann, J.C.; Nugeyre, M.T.; Chamaret, S.; Grest, J.; Dauget, C.; Axler-Blin, C.; Vézinet-Brun, F.; Rouzioux, C.; Rozenbaum, W.; Montagnier, L. Science 1983, 220, 868.
  52. 48. Miyoshi, I.; Taguchi, H.; Kobonishi, I.; Yoshimoto, S.; Ohtsuki, Y.; Shiraishi, Y.; Akagi, T. Gann. Monogr. 1982, 28, 219.
  53. 49. Ding, W.Q.; Liu, B.; Vaught, J.L.; Yamauchi, H.; Lind, S.E. Cancer Res. 2005, 65, 3389.

Similar Articles

1 2 3 > >> 

You may also start an advanced similarity search for this article.

Most read articles by the same author(s)