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Chemistry of phosphorus ylides 32: synthesis of phosphoranylidene-pyrano- and -cyclobutyl-xanthenones with potential antitumor activity

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Abstract

The reaction of active phosphacumulenes with xanthenones and anthrone yields xanthene(anthracene)- and/or phosphoranylidene xanthene(anthracene)- depending upon the nature of reactants and reaction conditions. Pertinent reaction mechanisms were considered and compatible spectroscopic measurements were recorded for all new compounds. The cytotoxic activity of some new products was evaluated against human cervical and breast carcinoma cell lines. Certain tested compounds showed promising results.

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References

  1. Hay AE, Aumond MC, Mallet S, Dumontet V, Litaudon M, Rondeau D, Richomme P (2004) J Nat Prod 67:707

    Article  CAS  Google Scholar 

  2. Mondal M, Puranik VG, Argade NP (2006) J Org Chem 71:4992

    Article  CAS  Google Scholar 

  3. Jung HA, Su BN, Keller WJ, Mehta RG, Kinghorn AD (2006) J Agric Food Chem 54:2077

    Article  CAS  Google Scholar 

  4. Lee BW, Lee JH, Lee ST, Lee HS, Lee WS, Jeong TS, Park KH (2005) Bioorg Med Chem Lett 15:5548

    Article  CAS  Google Scholar 

  5. Lin CN, Chung MI, Liou SJ, Lee TH, Wang TH (1996) J Pharm Pharmacol 48:532

    Article  CAS  Google Scholar 

  6. Dua VK, Ojha VP, Roy R, Joshi BC, Velacha N, Devi CU, Bhatnagar MC, Sharma VP, Subbarao SJ (2004) Ethnopharmacology 95:274

    Article  Google Scholar 

  7. Giri R, Goodell JR, Xing C, Benoit A, Kaur H, Hiasa H, Ferguson DM (2010) Bioorg Med Chem 18:1456

    Article  CAS  Google Scholar 

  8. Pedro M, Cerqueira F, Sousa ME, Nascimento MS, Pinto M (2002) Bioorg Med Chem 10:3725

    Article  CAS  Google Scholar 

  9. Valenti P, Bisi A, Rampa A, Belluti F, Gobbi S, Zampiron A, Carrara M (2002) Bioorg Med Chem 8:239

    Article  Google Scholar 

  10. Yoshimi N, Matsunaga K, Katayama M, Yamada Y, Kuno T, Qiao Z, Hara A, Yamahara J, Mori H (2001) Cancer Lett 163:163

    Article  CAS  Google Scholar 

  11. Saraiva L, Fresco P, Pinto E, Sousa E, Pinto M, Goncalves J (2002) Bioorg Med Chem 10:3219

    Article  CAS  Google Scholar 

  12. Saraiva L, Fresco P, Pinto E, Sousa E, Pinto M, Goncalves J (2003) Bioorg Med Chem 11:1215

    Article  CAS  Google Scholar 

  13. Nguemeving JR, Azebaze AGB, Kuete V, Carly NNE, Beng VP, Meyer M, Bland A, Bodo B, Nkengfack AE (2006) Phytochemistry 67:1341

    Article  CAS  Google Scholar 

  14. Demirkiran O (2007) Top Heterocycl Chem 9:139

    Article  CAS  Google Scholar 

  15. Wang Y, Shi JG, Wang MZ, Che CT, Yeung JH (2007) Life Sci 81:2016

    Google Scholar 

  16. Liu Y, Ma L, Chen WH, Wang B, Xu ZL (2007) Bioorg Med Chem 15:2810

    Article  CAS  Google Scholar 

  17. Soliman FM, Said MM, Maigali SS (2005) Heteroatom Chem 16:476

    Article  CAS  Google Scholar 

  18. Maigali SS, Said MM, Abd El-Maksoud MA, Soliman FM (2008) Monatsh Chem 139:495

    Article  CAS  Google Scholar 

  19. Said MM, Maigali SS, Abd El-Maksoud MA, Soliman FM (2008) Monatsh Chem 139:1299

    Article  CAS  Google Scholar 

  20. Soliman FM, Abd-Ellah I, Maigali SS, Abd-El-Naim G (2009) J Chem Res 277

  21. Bestmann HJ, Schmid G, Sandmeier D, Kisielowski L (1977) Angew Chem 89:275

    Article  CAS  Google Scholar 

  22. Matthews CN, Birum GH (1969) Acc Chem Res 2:373

    Article  CAS  Google Scholar 

  23. Vedejs E, Snoble KA (1973) J Am Chem Soc 95:5778

    Article  CAS  Google Scholar 

  24. Schlosser M, Piskala A, Tarchini C, Tuong HB (1975) Chimia 29:341

    CAS  Google Scholar 

  25. Bestmann HJ, Schmid G (1974) Angew Chem Int Ed 13:273

    Google Scholar 

  26. Johnson AW (1993) Ylides and imines of phosphorus. Wiley, New York

    Google Scholar 

  27. Grim SO, McFarlane W, Marks T (1967) Chem Commun 1191

  28. Surth YJ (2003) Nat Rev Cancer 3:750

    Google Scholar 

  29. Bestmann HJ (1977) Angew Chem Int Ed 16:349

    Article  Google Scholar 

  30. Bestmann HJ, Schmid G (1975) Tetrahedron Lett 4025

  31. Desai BM, Desai PR, Desai RD (1960) J Indian Chem Soc 37:53

    CAS  Google Scholar 

  32. Mustafa A, Hishmat OH (1975) J Am Chem Soc 79:2225

    Article  Google Scholar 

  33. Bestmann HJ, Sandmeier D (1975) Angew Chem Int Ed 14:634

    Google Scholar 

  34. Scheinmann F, Suschitzky H (1959) Tetrahedron 7:31

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Organometallic and Organometalloid Chemistry, National Research Centre, Dokki, Cairo, Egypt

    Fouad M. Soliman, Medhat M. Said & Shaban A. Darwish

  2. Faculty of Pharmacy, Biochemistry and Molecular Biology Department, Helwan University, Cairo, Egypt

    Mahmoud Youns

Authors
  1. Fouad M. Soliman
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  2. Medhat M. Said
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  3. Mahmoud Youns
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  4. Shaban A. Darwish
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Corresponding author

Correspondence to Fouad M. Soliman.

Electronic supplementary material

Below is the link to the electronic supplementary material. Figures showing the cytotoxic activity of the synthesized xanthenone derivatives 6, 9, 12a, 12b, 12d, 15, and 17 are available.

Supplementary material 1 (DOCX 197 kb)

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Soliman, F.M., Said, M.M., Youns, M. et al. Chemistry of phosphorus ylides 32: synthesis of phosphoranylidene-pyrano- and -cyclobutyl-xanthenones with potential antitumor activity. Monatsh Chem 143, 965–973 (2012). https://doi.org/10.1007/s00706-011-0683-3

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  • DOI: https://doi.org/10.1007/s00706-011-0683-3

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