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Synthesis of quinoxaline reverse ribofuranosides and their O-regioisomers

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Abstract

Six quinoxaline reverse nucleosides were prepared by reaction of quinoxalin-2-one derivatives with methyl 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-β-d-ribofuranoside in the presence of sodium hydride. For deprotection of quinoxaline nucleosides, heating in 60 % acetic acid was applied. The novel compounds were characterized by elemental analysis, mass spectra, and NMR data.

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References

  1. Khan SA, Saleem K, Khan Z (2008) Eur J Med Chem 43:2257

    Article  CAS  Google Scholar 

  2. Kotharkar SA, Shinde DB (2006) Bioorg Med Chem Lett 16:6181

    Article  CAS  Google Scholar 

  3. Zheng H, Jiang C, Chiu MH, Covey JM, Chan KK (2002) Drug Metab Dispos 30:344

    Article  CAS  Google Scholar 

  4. Cerecetto H, Dias E, Di Maio R, González M, Pacce S, Saenz P, Seoane G, Suescun L, Mombrú A, Fernández G, Lema M, Villalba J (2000) J Agric Food Chem 48:2995

    Article  CAS  Google Scholar 

  5. Chen Y, Cushing TD, Hao X, Reichelt AHX, Rzasa RM, Seganish J, Shin Y, Zhang D (2008) δ3-Substituted quinoline or quinoxaline derivatives and their use as phosphatidylinositol 3-kinase (PI3 K) inhibitors and their preparation. Chem Abstr 149:425813

    Google Scholar 

  6. Egawa M, Kawakami S, Ohsawa N, Inoue H, Seo S, Nomura R (2007) Quinoxaline derivative, and light emitting element, light emitting device, and electronic appliance using the same. Chem Abstr 146:325837

    Google Scholar 

  7. Kim KS, Bird LQ, Kickinson KE, Moreland S, Schaeffer TR, Waldron TI, Delany DL, Weller HN, Miller AV (1993) J Med Chem 36:2335

    Article  CAS  Google Scholar 

  8. Bandy RB, Greenblatt LP, Jirkovsky IL, Conklin M, Russo RJ, Bramlett DR, Emrey TA, Simmonds JT, Kowal DM, Stein RP, Tasse RP (1993) J Med Chem 36:331

    Article  Google Scholar 

  9. Ismail MM, Ammar YA, Ibrahim MK, El-Zahaby HS, Mahmoud S (2005) Arzneim Forsch 55:738

    CAS  Google Scholar 

  10. Moustafa OS, Yameda Y (2001) J Heterocycl Chem 38:809

    Article  CAS  Google Scholar 

  11. Bogatskii AV, Andronati SA (1979) Chem Heterocycl Comp 15:583

    Article  Google Scholar 

  12. Hazeldine ST, Polin L, Kushner J, Paluch J, White K, Edelstein M, Palomino E, Corbett TH, Horwitz JP (2001) J Med Chem 44:1758

    Article  CAS  Google Scholar 

  13. Fisherman JS, Osborn BL, Chun HG, Plowman J, Smith AC, Christian MC, Zaharko DS, Shoemaker RH (1993) Invest New Drugs 11:1

    Article  CAS  Google Scholar 

  14. El Ashry ESH, Abdel-Rahman AAH, Rashed N, Rasheed HA (1999) Pharmazie 54:893

    Google Scholar 

  15. Kovalenko M, Gazit A, Bohmer A, Rorsman C, Ronnstrand L, Heldin C, Waltenberger J, Bohmer FD, Levitzki A (1994) Cancer Res 54:6106

    CAS  Google Scholar 

  16. Ali IAI, Fathalla W (2006) Heteroatom Chem 17:280

    Article  CAS  Google Scholar 

  17. Ali IAI, Al-Masoudi IA, Hassan HG, Al-Masoudi NA (2007) Chem Heterocycl Comp 438:1052

    Article  Google Scholar 

  18. Ali IAI, Al-Masoudi IA, Saeed B, Al-Masoudi NA, La Colla P (2005) Heteroatom Chem 16:148

    Article  CAS  Google Scholar 

  19. Fathalla W, Ali IAI (2007) Heteroatom Chem 18:637

    Article  CAS  Google Scholar 

  20. Fathalla W, El Rayes SM, Ali IAI (2007) Arkivoc xvi:173

    Article  Google Scholar 

  21. El Rayes SM, Ali IAI, Fathalla W (2008) Arkivoc xi:86

    Article  Google Scholar 

  22. Ali IAI, Fathalla W, El Rayes SM (2008) Arkivoc iii:179

    Article  Google Scholar 

  23. Abdel-Rahman AAH, Abdel-Megied AES, Goda AES, Zeid IF, El Ashry ESH (2003) Nucleosides. Nucleotides Nucleic Acids 22:2027

    Article  CAS  Google Scholar 

  24. Kazimierczuk Z, Pfleiderer W (1982) Liebigs Ann Chem 61:754

    Article  Google Scholar 

  25. Burger K, Eggersdorfer M (1979) Liebigs Ann Chem 58:1547

    Article  Google Scholar 

  26. Okada K, Sakuma H, Kondo M, Inoue S (1979) Chem Lett 8:213

    Article  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Suez Canal University, Ismailia, Egypt

    Ibrahim A. I. Ali & Samir M. El Rayes

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  1. Ibrahim A. I. Ali
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  2. Samir M. El Rayes
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Correspondence to Ibrahim A. I. Ali.

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Ali, I.A.I., El Rayes, S.M. Synthesis of quinoxaline reverse ribofuranosides and their O-regioisomers. Monatsh Chem 145, 1371–1380 (2014). https://doi.org/10.1007/s00706-014-1193-x

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  • DOI: https://doi.org/10.1007/s00706-014-1193-x

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