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Research on Chemical Intermediates

, Volume 45, Issue 2, pp 127–154 | Cite as

Microwave-assisted and thermal synthesis of nanosized thiazolyl-phenothiazine derivatives and their biological activities

  • Manal M. Alsharekh
  • Ismail I. Althagafi
  • Mohamed R. Shaaban
  • Thoraya A. FarghalyEmail author
Article
  • 66 Downloads

Abstract

Efficient synthesis of a series of nanosized phenothiazine derivatives incorporating thiazole moiety was achieved using microwave irradiation as well as thermal conditions. Reaction of 2-(1-(10H-phenothiazin-2-yl)ethylidene)hydrazine-1-carbothioamide with various types of hydrazonoyl halide or α-haloketone afforded corresponding thiazolyl phenothiazines in good to excellent yield. Mass, 1H and 13C nuclear magnetic resonance (NMR), ultraviolet–visible (UV–Vis), X-ray diffraction (XRD), and elemental analyses confirmed the structure of all the new derivatives. The reaction progressed under microwave irradiation in shorter reaction time with higher yield compared with the conventional method. The antimicrobial and antitumor activities of selected derivatives were investigated, revealing that some of them showed high potency compared with standard references.

Keywords

Phenothiazines Thiosemicarbazone Thioamides Hydrazonoyl halides α-Haloketones Thiazoles Antimicrobial Anticancer Microwaves 

Notes

Acknowledgements

This work was supported by King Abdulaziz City for Science and Technology, Riyadh, Saudi Arabia (grant no. 37-1683 for postgraduate students).

References

  1. 1.
    S. Caddick, Tetrahedron 51, 10403 (1995)CrossRefGoogle Scholar
  2. 2.
    A.K. Bose, M. Jayaraman, A. Okawa, S.S. Barie, E.W. Robb, M.S. Manhas, Tetrahedron Lett. 37, 6989 (1996)CrossRefGoogle Scholar
  3. 3.
    O. Kappe, Angew. Chem. Int. Ed. Engl. 43, 6250 (2004)CrossRefGoogle Scholar
  4. 4.
    M. Fontecave, S. Ollagnier-de-Choudens, E. Mulliez, Chem. Rev. 103, 2149 (2003)CrossRefGoogle Scholar
  5. 5.
    J. Quiroga, P. Hernandez, B. Insuasty, R. Abonia, J. Cobo, A. Sanchez, M. Nogueras, J.N. Low, J. Chem. Soc. Perkin Trans. 1(4), 555 (2002)CrossRefGoogle Scholar
  6. 6.
    S.F. Mohamed, E.M.H. Abbas, H.S. Khalaf, T.A. Farghaly, D.N. Abd El-Shafy, Mini-rev. Med. Chem. 18, 18 (2018)CrossRefGoogle Scholar
  7. 7.
    K.D. Hargrave, F.K. Hess, J.T. Oliver, J. Med. Chem. 26, 1158 (1983)CrossRefGoogle Scholar
  8. 8.
    W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, D.G. Taylor, C.J.C. Connolly, A.M. Doherty, S.R. Klutchko, I.B. Sircar, A. Steinbaugh, B.L. Batley, C.A. Painchaud, S.T. Rapundalo, B.M. Michniewicz, S.C.J. Olson, J. Med. Chem. 35, 2562 (1992)CrossRefGoogle Scholar
  9. 9.
    R.N. Sharma, F.P. Xavier, K.K. Vasu, S.C. Chaturvedi, S.S. Pancholi, J. Enz. Inhib. Med. Chem. 24, 890 (2009)CrossRefGoogle Scholar
  10. 10.
    J.C. Jaen, L.D. Wise, B.W. Caprathe, H. Tecle, S. Bergmeier, C.C. Humblet, T.G. Heffner, L.T. Meltzner, T.A. Pugsley, J. Med. Chem. 33, 311 (1990)CrossRefGoogle Scholar
  11. 11.
    K. Tsuji, H. Ishikawa, Bioorg. Med. Chem. Lett. 4, 1601 (1994)CrossRefGoogle Scholar
  12. 12.
    F.W. Bell, A.S. Cantrell, M. Hogberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordon, M.D. Kinnick, P. Lind, J.M. Morin, R. Noreen, B. Oberg, J.A. Palkowitz, C.A. Parrish, P. Pranc, C. Sahlberg, R.J. Ternansky, R.T. Vasileff, L. Vrang, S.J. West, H. Zhang, X.X.J. Zhou, J. Med. Chem. 38, 4929 (1995)CrossRefGoogle Scholar
  13. 13.
    N. Ergenc, G. Capan, N.S. Gunay, S. Ozkirimli, M. Gungor, S. Ozbey, E. Kendi, Arch. Pharm. Med. Chem. 332, 343 (1999)CrossRefGoogle Scholar
  14. 14.
    J.S. Carter, S. Kramer, J.J. Talley, T. Penning, P. Collins, M.J. Graneto, K. Seibert, C. Koboldt, J. Masferrer, B. Zweifel, Bioorg. Med. Chem. Lett. 9, 1171 (1999)CrossRefGoogle Scholar
  15. 15.
    A. Badorc, M.F. Bordes, P. De Cointet, P. Savi, A. Bernat, A. Lale, M. Petitou, J.P. Maffrand, J.M. Herbert, J. Med. Chem. 40, 3393 (1997)CrossRefGoogle Scholar
  16. 16.
    J. Rudolph, H. Theis, R. Hanke, R. Endermann, L. Johannsen, F.U. Geschke, J. Med. Chem. 44, 619 (2001)CrossRefGoogle Scholar
  17. 17.
    A. Kleemann, J. Engel, in Pharmaceutical Substances, 4th edn (2001)Google Scholar
  18. 18.
    L.Y. Wang, C.X. Zhang, Z.Q. Liu, D.Z. Lio, Z.H. Jang, S.P. Yan, Inorg. Chem. Commun. 6, 1255 (2003)CrossRefGoogle Scholar
  19. 19.
    A.H. Al-Dujali, A.T. Atto, A.M. Al-Kurde, Eur. Polym. J. 37, 927 (2001)CrossRefGoogle Scholar
  20. 20.
    Y. Li, Y. Xu, X. Qian, B. Qu, Tetrahedron Lett. 45, 1247 (2004)CrossRefGoogle Scholar
  21. 21.
    I. Tintcheva, V. Maximova, T. Deligeorgiev, D. Zaneva, I. Ivanov, J. Photochem. Photobiol. A Chem. 130, 7 (2000)CrossRefGoogle Scholar
  22. 22.
    V.C. Rucker, S. Foister, C. Melander, P.B. Dervan, J. Am. Chem. Soc. 125, 1195 (2003)CrossRefGoogle Scholar
  23. 23.
    Q. Wang, H. Li, Y. Li, R. Huang, J. Agric. Food Chem. 52, 1918 (2004)CrossRefGoogle Scholar
  24. 24.
    K. Yanagimoto, K.G. Lee, H. Ochi, T. Shibamoto, J. Agric. Food Chem. 50, 5480 (2002)CrossRefGoogle Scholar
  25. 25.
    K. Pluta, B. Morak-Młodawska, M. Jeleń, Eur. J. Med. Chem. 46, 3179 (2011)CrossRefGoogle Scholar
  26. 26.
    N.G. Kandile, H.T. Zaky, M.I. Mohamed, H.M. Mohamed, Bull. Korean Chem. Soc. 31, 3530 (2010)CrossRefGoogle Scholar
  27. 27.
    J. Li, D. Guo, X. Wang, H. Wang, H. Jiang, B. Chen, Nanoscale Res. Lett. 5, 1063 (2010)CrossRefGoogle Scholar
  28. 28.
    C. Viegas-Junior, A. Danuello, V.S. Bolzani, E.J. Barreiro, C.A.M. Fraga, Curr. Med. Chem. 14, 1829 (2007)CrossRefGoogle Scholar
  29. 29.
    N.F. Eweiss, A.O. Osman, J. Heterocycl. Chem. 17, 1713 (1980)CrossRefGoogle Scholar
  30. 30.
    A.S. Shawali, H.A. Albar, Can. J. Chem. 64, 871 (1986)CrossRefGoogle Scholar
  31. 31.
    S.M. Gomha, S.M. Riyadh, E.A. Mahmmoud, M.M. Elaasser, Heterocycles 91(6), 1227 (2015)CrossRefGoogle Scholar
  32. 32.
    T. Mosmann, J. Immunol. Methods 65, 55 (1983)CrossRefGoogle Scholar
  33. 33.
    K.S. Ravindra, K.S. Ashok, J. Mol. Struct. 1094, 61 (2015)CrossRefGoogle Scholar
  34. 34.
    M.J.M. Campbell, Coord. Chem. Rev. 15, 279 (1975)CrossRefGoogle Scholar
  35. 35.
    B. Fábián, V. Kudar, A. Csámpai, T. Zs, J. Organomet. Chem. 692, 5621 (2007)CrossRefGoogle Scholar
  36. 36.
    Y. Tian, C. Duan, C. Zhao, X. You, T.C.W. Mak, Z.Y. Zhang, Inorg. Chem. 36, 1247 (1997)CrossRefGoogle Scholar
  37. 37.
    S.A. Reddy, K.J.K. Reddy, S.L. Narayana, A.V. Reddy, Food Chem. 109, 654 (2008)CrossRefGoogle Scholar
  38. 38.
    K.F. Khaled, Electrochim. Acta 55, 5375 (2010)CrossRefGoogle Scholar
  39. 39.
    S. Christian, A. Zaynab, J. Patric, D. Jansson, S. Kalinowski, D.R. Richardso, J. Inorg. Biochem. 152, 20 (2015)CrossRefGoogle Scholar
  40. 40.
    A. Kusaï, L. Anne, A. Magali, B. Gilles, L. Gérald, J. Inorg. Biochem. 126, 76 (2013)CrossRefGoogle Scholar
  41. 41.
    R. Nandhagopal, D. Neelakandan, G. Gajendra, L.N. Vadithe, K. Ahmed, N. Narayana, T. Bruno, J. Organomet. Chem. 794, 104 (2015)CrossRefGoogle Scholar
  42. 42.
    J. Zhang, H. Geng, L. Zhuang, G. Wang, Acta Crystallogr. Sect. E Struct. Rep. 65, 02244 (2009)CrossRefGoogle Scholar
  43. 43.
    S. Al-Ashqer, K.S. Abou-Melha, G.A.A. Al-Hazmi, F.A. Saad, N.M. El-Metwaly, Mol. Biomol. Spectrosc. 132, 751 (2014)CrossRefGoogle Scholar
  44. 44.
    A.S. Shawali, M.M. Zayed, T.A. Farghaly, J. Heterocyclic Chem. 42, 185 (2005)CrossRefGoogle Scholar
  45. 45.
    A.S. Shawali, M.H. Abdel-kader, F.A. Altalbawy, Tetrahedron 58, 2875 (2002)CrossRefGoogle Scholar
  46. 46.
    T.A. Farghaly, A.S. Shawali, Tetrahedron 66, 2700 (2010)CrossRefGoogle Scholar
  47. 47.
    A.S. Shawali, T.A. Farghaly, Tetrahedron 60, 3051 (2004)CrossRefGoogle Scholar
  48. 48.
    A.S. Shawali, S.M. Sherif, T.A. Farghaly, M.R. Shehata, M.A.A. Darwish, J. Chem. Res. 1, 44 (2007)CrossRefGoogle Scholar
  49. 49.
    T.A. Farghaly, Z.A. Abdallah, Arkivok 17, 295 (2008)Google Scholar
  50. 50.
    S. Jubie, S. Meena, K.V. Ramaseshu, N. Jawahar, S. Vijayakumar, Indian J. Chem. Sect. B 49B, 1261 (2010)Google Scholar
  51. 51.
    A.Z. El-Sonbatia, M.A. Diaba, A.A. El Bindarya, M.M. Ghoneimb, M.T. Mohesienc, M.K. Abd El-Kader, J Mol. Liq. 215, 711 (2016)CrossRefGoogle Scholar
  52. 52.
    F. Saad, N. El-Metwaly, T.A. Farghaly, M. Elghalban, R. Shah, G. Al-Hazmi, K. Saleh, M. Alfaifi, J. Mol. Liq. 229, 614 (2017)CrossRefGoogle Scholar
  53. 53.
    A. Shahrjerdi, S.S.H. Davarani, E. Najafi, M.M. Amini, Ultrason. Sonochem. 22, 382 (2015)CrossRefGoogle Scholar
  54. 54.
    B.D. Cullity, Measurement of Residual Stress. Elements of X-Ray Diffraction, 2nd edn. (Addison-Wesley, Boston, 1978), pp. 447Google Scholar
  55. 55.
    M. Reig, R. Bosque, M. Font-Bardía, C. Calvis, R. Messeguer, L. Baldomà, J. Badía, D. Velasco, C. López, J. Inorg. Biochem. 182, 1 (2018)Google Scholar
  56. 56.
    T.A.R. Santos, A.C. Silva, E.B. Silva, P.A.T.M. Gomes, J.W.P. Espíndola, M.V.O. Cardoso, D.R.M. Moreira, A.C.L. Leite, V.R.A. Pereira, Biomed. Pharmacother. 82, 555 (2016)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Manal M. Alsharekh
    • 1
  • Ismail I. Althagafi
    • 1
  • Mohamed R. Shaaban
    • 1
    • 2
  • Thoraya A. Farghaly
    • 2
    Email author
  1. 1.Department of Chemistry, Faculty of Applied ScienceUmm Al-Qura UniversityMakkah AlmukkarramahSaudi Arabia
  2. 2.Department of Chemistry, Faculty of ScienceCairo UniversityGizaEgypt

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