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Vol. 28 No. 12 (2016): Vol 28 Issue 12

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Synthesis, Stereochemistry and Antimicrobial Activity of Some Novel Flavanone-hydrazono-thiazolidin-4-ones from Flavanones

https://doi.org/10.14233/ajchem.2016.19908
Sayeed Mukhtar
Department of Chemistry, Faculty of Science, University of Tabuk, Tabuk, Kingdom of Saudi Arabia
Mohammed Issa Al-Ahmdi
Department of Chemistry, Faculty of Science, University of Tabuk, Tabuk, Kingdom of Saudi Arabia
Humaira Parveen
Department of Chemistry, Faculty of Science, University of Tabuk, Tabuk, Kingdom of Saudi Arabia

Corresponding Author(s) : Sayeed Mukhtar

sayeed_mukhtar@hotmail.com

Asian Journal of Chemistry, Vol. 28 No. 12 (2016): Vol 28 Issue 12

Abstract

The synthesis of four novel compounds, (i) E-2-{[2-(4-methoxyphenyl)chroman-E-4-ylidene]hydrazono}thiazolidin-4-one (4a), (ii) E-2-{[2-(4-methoxyphenyl)chroman-Z-4-ylidene]hydrazono}thiazolidin-4-one (5a), (iii) E-2-{[2-(phenyl)chroman-E-4-ylidene]hydrazono}-thiazolidin-4-one (4b) and (iv) E-2-{[2-(phenyl)chroman-Z-4-ylidene]hydrazono}thiazolidin-4-one (5b) from 4'-methoxy flavanone (1a) in (i) and (ii) and from flavanone (1b) in (iii) and (iv) via the reaction of respective thiosemicarbazones (2a) and (2b), with chloroacetic acid and sodium acetate in acetic acid is described. Structural assignment, stereochemistry and biological assays are discussed.

Keywords

Flavanone Thiosemicarbazone Thiazolidin-4-ones Antimicrobial activity
Mukhtar, S., Al-Ahmdi, M. I., & Parveen, H. (2016). Synthesis, Stereochemistry and Antimicrobial Activity of Some Novel Flavanone-hydrazono-thiazolidin-4-ones from Flavanones. Asian Journal of Chemistry, 28(12), 2589–2595. https://doi.org/10.14233/ajchem.2016.19908
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References
  1. A.K. Jain, A. Vaidya, V. Ravichandran, S.K. Kashaw and R.K. Agrawal, Bioorg. Med. Chem.. 20, 3378 (2012); doi:10.1016/j.bmc.2012.03.069.
  2. C.V. Kavitha Basappa, S.N. Swamy, K. Mantelingu, S. Doreswamy, M.A. Sridhar, J. Shashidhara Prasad and K.S. Rangappa, Bioorg. Med. Chem., 14, 2290 (2006); doi:10.1016/j.bmc.2005.11.017.
  3. M.S. Chande and V. Suryanarayan, J. Chem. Res., 345 (2005); doi:10.3184/0308234054506749.
  4. M.G. Vigorita, R. Ottana, F. Monforte, R. Maccari, A. Trovato, M.T. Monforte and M.F. Taviano, Bioorg. Med. Chem. Lett., 11, 2791 (2001); doi:10.1016/S0960-894X(01)00476-0.
  5. S.G. Kucukguzel, E.E. Oruc, S. Rollas, F. Sahin and A. Ozbek, Eur. J. Med. Chem., 37, 197 (2002); doi:10.1016/S0223-5234(01)01326-5.
  6. W.E. Grundy, A.I. Whitman, E.G. Rdzok, E.J. Rdzok, M.E. Haris and J.C. Sylvester, Antibiot. Chemother., 2, 399 (1952).
  7. A. Upadhyay, S.K. Srivastava and S.D. Srivastava, Eur. J. Med. Chem., 45, 3541 (2010); doi:10.1016/j.ejmech.2010.04.029.
  8. R. Ramachandran, M. Rani and S. Kabilan, Bioorg. Med. Chem. Lett., 19, 2819 (2009); doi:10.1016/j.bmcl.2009.03.093.
  9. R.C. Sharma and D. Kumar, J. Indian Chem. Soc., 77, 492 (2000).
  10. S.B. Desai, P.B. Desai and K.R. Desai, Asian J. Chem., 15, 363 (1999).
  11. E. Piscapo, M.V. Diurno, R. Gagliardi and O. Mazzoni, Boll. Soc. Ital. Biol. Sper., 65, 853 (1989).
  12. D. Kini and M. Ghate, E-J. Chem., 8, 386 (2011); doi:10.1155/2011/258680.
  13. R. Maccari, A.D. Corso, M. Giglio, R. Moschini, U. Mura and R. Ottana, Bioorg. Med. Chem. Lett., 21, 200 (2011); doi:10.1016/j.bmcl.2010.11.041.
  14. R. Ottanà, R. Maccari, M. Giglio, A. Del Corso, M. Cappiello, U. Mura, S. Cosconati, L. Marinelli, E. Novellino, S. Sartini, C. La Motta and F. Da Settimo, Eur. J. Med. Chem., 46, 2797 (2011); doi:10.1016/j.ejmech.2011.03.068.
  15. H.N. Hafez and A.B.A. El-Gazzar, Bioorg. Med. Chem. Lett., 19, 4143 (2009); doi:10.1016/j.bmcl.2009.05.126.
  16. J. Balzarini, B. Orzeszko-Krzesinska, J.K. Maurin and A. Orzeszko, Eur. J. Med. Chem., 44, 303 (2009); doi:10.1016/j.ejmech.2008.02.039.
  17. H. Chen, J. Bai, L. Jiao, Z. Guo, Q. Yin and X. Li, Bioorg. Med. Chem., 17, 3980 (2009); doi:10.1016/j.bmc.2009.04.024.
  18. H. Chen, Z. Guo, Q. Yin, X. Duan, Y. Gu and X. Li, Front. Chem. Sci. Eng., 5, 231 (2011); doi:10.1007/s11705-010-1022-7.
  19. A. Kumar, C.S. Rajput and S.K. Bhati, Bioorg. Med. Chem., 15, 3089 (2007); doi:10.1016/j.bmc.2007.01.042.
  20. A. Deep, S. Jain and P.C. Sharma, Acta Poloniae Pharm.-Drug Res., 67, 63 (2010).
  21. K.M. Amin, M.M. Kamel, M.M. Anwar, M. Khedr and Y.N. Syam, Eur. J. Med. Chem., 45, 2117 (2010); doi:10.1016/j.ejmech.2009.12.078.
  22. M.V. Diurno, O. Mazzoni, G. Correale, I. Gomez Monterrey, A. Calignano, G. La Rana and A. Bolognese, Farmaco, 54, 579 (1999); doi:10.1016/S0014-827X(99)00064-6.
  23. Y. Tagami, T. Yamaguchi, J. Kubo, J. Shimozono, K. Yonemuna and M. Mukai, Japanese Patent 0903067 (1997); Chem. Abstr., 126, 171592u (1997).
  24. T. Previtera, M.G. Vigorita, M. Basile, F. Orsini, F. Benetollo and G. Bombieri, Eur. J. Med. Chem., 29, 317 (1994); doi:10.1016/0223-5234(94)90102-3.
  25. D.A. Walsh and I.M. Uwaydah, US Patent 5061720 (1991); Chem. Abstr.116, 59362m (1992).
  26. T. Kato, T. Ozaki, K. Tamura, Y. Suzuki, M. Akima and N. Ohi, J. Med. Chem., 42, 3134 (1999); doi:10.1021/jm9900927.
  27. N.A. Castle, M. Gross and J.S. Mendoz, PCT Int Appl. WO 9962891, Chem. Abstr., 132, 12317 (2000).
  28. B. Valleskey, M. Juliana, D.C. Hunder, C.D. John, J.A. Panetta and W.N. Shaw, Eur. Patent 587377 (1994); Chem. Abstr., 121, 35596t (1994).
  29. 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); doi:10.1039/p19950000935.
  30. Y. Tanabe, G. Suzukamo, Y. Komuro, N. Imanishi, S. Morooka, M. Enomoto, A. Kojima, Y. Sanemitsu and M. Mizutani, Tetrahedron Lett., 32, 379 (1991); doi:10.1016/S0040-4039(00)92633-9.
  31. Y. Hanasaki, S. Ogawa and S. Fukui, Free Radic. Biol. Med., 16, 845 (1994); doi:10.1016/0891-5849(94)90202-X.
  32. S. Mukhtar, M.V.P. Rahman, W.H. Ansari, G. Lemière, A. De Groot and R. Dommisse, Molecules, 4, 232 (1999); doi:10.3390/40700232.
  33. V.P.M. Rahman, S. Mukhtar, W.H. Ansari and G. Lemiere, Eur. J. Med. Chem., 40, 173 (2005); doi:10.1016/j.ejmech.2004.10.003.
  34. N.P. Buu-Hoi, N.D. Xuong and F. Binon, J. Chem. Soc., 713 (1956); doi:10.1039/JR9560000713.
  35. T.S. Gardner, F.A. Smith, E. Wenis and J. Lee, J. Org. Chem., 16, 1121 (1951); doi:10.1021/jo50001a015.
  36. V.S. Ingle, A.R. Swale, R.D. Ingle and R.A. Mane, Indian J. Chem., 40B, 124 (2001).
  37. G.N. Vyas and N.M. Shah, J. Indian Chem. Soc., 28, 75 (1951).
  38. N. Takeno, T. Fukushima, S. Takeda and K. Kishimoto, Bull. Chem. Soc. Jpn., 58, 1599 (1985); doi:10.1246/bcsj.58.1599.
  39. F. Kally, G. Janzso and I. Koczor, Tetrahedron, 21, 19 (1965); doi:10.1016/S0040-4020(01)82197-9.
  40. C. Perez, M. Pauli and P. Bazerque, Acta Biol. Med. Exp., 15, 113 (1990).
  41. A.Z. Beg and I. Ahmad, World J. Microbiol. Biotechnol., 16, 841 (2000); doi:10.1023/A:1008991724288.
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