Azoniallene Salts: Synthesis and their Utility in Heterocyclic Synthesis

Azoniallene Salts: Synthesis and their Utility in Heterocyclic Synthesis

Loading document ...
Page
of
Loading page ...

Author(s)

Author(s): Mohamed E. Khalifa, Ahmed S. Radwan, El-Sayed H. Al-Tamany, Ehab Abdel-Latif

Download Full PDF Read Complete Article

493 1053 68-86 Volume 2 - Oct 2013

Abstract

A series of novel 5-arylazo-thiazol-2-ylcarbamoyl-thiophene derivatives was synthesized and their chemical structures were secured by elemental and spectroscopic analyses. Their versatility for pharmaceutical purposes and textile dyeing as disperse dyes was reported. The synthesized dyes were applied to polyester fabrics by using high temperature dyeing method at 130°C. The dyed polyester fabrics, which display yellowish-brown to brown hues, were displayed excellent washing and perspiration fastness and moderate light fastness. Finally, the synthesized compounds showed biological activities against Bacillus subtilise, Staphylococcus aureus (Gram positive bacteria), Escherichia coli, Pseudomonas aeruginosa (Gram negative bacteria), while no effect had been reported against Fungi. The minimum inhabitation concentration of the most active compound was evaluated.

Keywords

2-Aminothiazole, Biological activity, Disperse dyes, Fastness properties, Polyester fibers, Thiophene

References

  1. Hayakawa, I.; Tanaka, Y.; Nagata, Y. Japan Kokai, 1976, 77, 588; Chem. Abstr., 88, 37785c, 1978
  2. Ibatullin, U.G.; Petrushina, T.F.; Leitis, L.Y.; Minibaev, I.Z.; Logvin, B.O. Khim. Geterotsitl. Soedin., 1993, 12, 715
  3. Singh. K.; Singh, S.; Taylor, J.A. Dyes and Pigments, 2002, 54, 189
  4. Beyer, H.; Stehwien D. Arch Pharm, 1953, 286(1), 13
  5. Hang, P.C.; Honek, J.F. Bioorg. Med. Chem. Lett., 2005, 15, 1471
  6. Beuchet, P.; Varache-Lembège, M.; Neveu, A.; Léger, J.M.; Vercauteren, J.; Larrouture, S,; Deffieux, G.; Nuhrich, A. Eur. J. Med. Chem., 1999, 34, 773
  7. Geronikaki, A.; Vicini, P.; Dabarakis, N.; Lagunin, A.; Poroikov, V.; Dearden, J.; Modarresi, H.; Hewitt, M.; Theophilidis G. Eur. J. Med. Chem, 2009, 44, 473
  8. Papadopoulou, C.; Geronikaki, A.; Hadjipavlou-Litina, D. II Farmaco, 2005, 60, 969
  9. Kreutzberger, A.; Schimmelpfennig, H. Arch. Pharm., 1981, 314, 385
  10. Metwally, M.A.; Abdel-latif, E.; Khalil, A.M.; Amer, F.A.; Kaupp, G. Dyes and Pigments, 2004, 62, 181
  11. Metwally, M.A.; Abdel-Latif, E.; Amer, F.A. J. Text. Assoc., 2001, 63, 155
  12. Metwally, M.A.; Abdel-Latif, E.; Amer, F.A. J. Text. Assoc., 2002, 149
  13. Metwally, M.A.; Etman, H.A.; Gafer, H.E.; Khalil A.M. Advances in Color Science and Technology, 2004, 7, 71
  14. Metwally, M.A.; Abdel-Latif, E.; Amer, F.A.; Kaupp, G. Dyes and Pigments, 2004, 60, 249
  15. Metwally, M.A.; Abdel-Latif, E.; Amer, F.A.; Kaupp, G. Dyes and Pigments, 2004, 62, 181
  16. Romagnoli, R.; Baraldi, P.V.; Carrion, M.D.; Cara, C.L.; Cruz-Lopez, O.; Preti, D.; Tolomeo, M.; Grimaudo, S.; Di Cristina, A.; Zonta, N.; Balzarini, J.; Brancale, A.; Sarkar, T.; Hamel, E. Bioorg Med Chem, 2008, 16, 5367
  17. Bondock, S.; Fadaly, W.; Metwally, M.A. Eur J Med Chem, 2010, 45, 3692
  18. Gaber, H.M.; Bagley, M.C.; Sherif, S.M. Eur J Chem, 2010, 1, 115
  19. Grese, T.A.; Cho, S.; Finley, D.R.; Godfrey, A.G.; Jones, C.D.; Lugar, C.; Martin, M.; Matsumoto, K.; Pennington, L.; Winter, M.A.; Adrian, M.D.; Cole, H.W.; Magee, D.E.; Phillips, D.L.; Rowley, E.R.; Short, L.L.; Glasebrook, A.L.; Bryant, H.U. J. Med. Chem., 1997, 40, 146
  20. Takeuchi, K.; Kohn, T.J.; Sall, D.J.; Denney, M.L.; McCowan, J.R.; Smith, G.F.; Gifford-Moore, D.S. Bioorg. Med. Chem. Lett., 1999, 9, 759
  21. Romagnoli, R.; Baraldi, P.G.; Carrion, M.D.; Cara, C.L.; Preti, D.; Fruttarolo, F.; Pavani, M.G.; Tabrizi, M.A.; Tolomeo, M.; Grimaudo, S.; Di Cristina, A.; Balzarini, J.; Hadfield, J.A.; Brancale, A.; Hamel, E. J. Med. Chem., 2007, 50, 2273
  22. Miller, T.A.; Witter, D.J.; David, J.; Belvedene, S. PCT Inl. Appl. WO, 2005, 034880, Chem Abstr. 2005, 142, 392278
  23. Radwan, M.A.A.; Shehab, M.A.; El-Shenawy, S.M. Monatsch. Chem., 2009, 140, 445
  24. Merriman, G.H.; Weintraub, P.M.; Sabol, J.S.; Dharanipragada, R.; Hrib, N.J.; Jurcak, J.G.; Gross, A.; Whiteley, B.; Musick, K.Y.; Klein, J. PCT Int. Appl. WO, 2003, 091215, Chem. Abstr. 2003, 139, 364826
  25. Callahan, J.F.; Wan, Z. PCT Int. Appl. WO, 2003, 104219, Chem. Abstr. 2004, 140, 27756
  26. Abreu, R.M.V.; Ferreira, I.C.F.R.; Queiroz, M.J.R.P. Eur. J. Med. Chem., 2009, 44,1952
  27. Metwally, M.A.; Khalifa, M.E.; Amer, F.A. Dyes and Pigments, 2008, 76, 379
  28. Metwally, M.A.; Khalifa, M.E.; Amer, F.A. Mens Agitat, 2009, 4, 81
  29. Gaffer, H.E.; Khalifa, M.E.; El-Bially, S.F.; Metwally, M.A. Macdonian Journal of Chemistry and Chemical Engineering, 2010, 29, 87
  30. Abdel-Latif, E.; Metwally, M.A.; Amer, F.A.; Khalifa, M.E. Pigment and Resin Technology, 2009, 38, 105
  31. Metwally, M.A.; Khalifa, M.E.; Adel-Latif, E.; Amer, F.A. Polish Journal of Chemical Technology, 2010, 12, 1
  32. Khalifa, M.E.; Metwally, M.A.; Adel-Latif, E.; Amer, F.A. International Journal of Textile Science, 2012, 1, 62
  33. Khalifa, M.E.; Amin, M.A.; Abdel-Latif, E. International Journal of Chemistry, 2013, 34, 1157
  34. Adel-Latif, E.; Metwally, M.A.; Khalifa, M.E.; Amer, F.A. International Journal of Textile Science, 2012, 1, 1
  35. Elgemeie, G.H.; Helal, M.H.; Abbas, E.M.; Abdel Mowla, E.A. Pigment Resin Tech, 2002, 31, 365
  36. Bello, K.A. Dyes and Pigments, 1995, 27, 45
  37. Egli, R.; Peters, A.T.; Freeman, H.S. Colour Chemistry: The Design and Synthesis of Organic Dyes and Pigments, Chapter 1, Elsevier, London, 1999
  38. Ho, Y.W.; Yao, W.H. Dyes and Pigments, 2006, 70, 60
  39. Ho, Y.W. Dyes and Pigments 2005, 64, 223
  40. Metwally, M.A.; Abdel-latif, E.; Amer, F.A. Sulfur Letters, 2003, 26(3), 119
  41. Goerdeler, J.; Keuser, U. Chem. Ber. 1963, 97(11), 3106
  42. Anon. Standard Methods for the Determination of the Colour Fastness of Textiles and Leather, 5th Edn, Society of Dyes and Colorists Publication, Bradford, England, 1990
  43. Al-Etaibi, A.M.; El-Apasery.; M.A.; Ibrahim, M.R.; Al-Awadi, N.A. Molecules, 2012, 17, 13891
  44. Chipalkatti, H.R.; Desai, N.F.; Giles, C.H.; Macaulay, N. J. Soc. Dyers Colour, 1954, 70, 487
  45. Műller, C. American Dyestuff Reporter, 1970, 59, 37
  46. National Committee for Clinical Laboratory Standards. 1997
  47. Methods for dilution antimicrobial susceptibility test for bacteria that grow aerobically, Approved standard, 4th ed. M7-A4
  48. El-Saied, F.A.; Abdel-Latif, E.; Nawar, A.M.; Radwan, A.S.; Hamed, A.A. Smart Nanocomposites, 2012, 3(1), 17
  49. Beyer, H.; Wolter, G. Chem. Ber., 1952, 85(11), 1077

Cite this Article:

International Journal of Sciences is Open Access Journal.
This article is licensed under a Creative Commons Attribution 4.0 International (CC BY 4.0) License.
Author(s) retain the copyrights of this article, though, publication rights are with Alkhaer Publications.

Search Articles

Issue June 2024

Volume 13, June 2024


Table of Contents



World-wide Delivery is FREE

Share this Issue with Friends:


Submit your Paper