Skip to main content

Advertisement

SpringerLink
Log in

Synthesis of some fused heterocyclic systems and their nucleoside candidates

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A series of pyridofuro compounds were synthesized from 4-(4-chlorophenyl)-1,2-dihydro-2-oxo-6-(thiophen-2-yl)pyridine-3-carbonitrile (1) as starting material. Alkylation of 1 with ethyl bromoacetate gave the corresponding ester 2, which was condensed with hydrazine hydrate to afford the corresponding acid hydrazide derivative 3. Thrope-Ziegler cyclization of 2 with sodium methoxide gave furo[2,3-b]pyridine derivative 4, which was reacted with thiosemicarbazide, allyl isothiocyanate, formamide or hydrazine hydrate to give furopyridine derivatives 5–8, respectively. The latter compound 8 was cyclized with acetylacetone or formic acid to give the corresponding compounds 9 and 10, respectively. Furthermore, sulfurization of 1 with P2S5 gave the corresponding thioxopyridine 11, which was reacted with glycosyl (or galactosyl) bromide, morpholine or piperidine to give the corresponding thioglycoside 12a,b and Mannich base 14a,b derivatives. The deacetylation of 12a,b gave the corresponding deacetylated thioglycosides 13a,b, respectively. All the newly synthesized compounds were characterized by the elemental analyses and spectroscopic evidences (IR, 1H- and 13C NMR).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. H. Rapoport, A.P. Van Sickle, J. Org. Chem. 55, 895 (1990)

    Article  Google Scholar 

  2. J.M. Hoffman Jr., US Patent 4, 808, 595, 1989. Chem. Abstr. 111, 115159 m (1989)

  3. G. Wagner, J. Prantz, Pharmazie 48, 250 (1993)

    CAS  Google Scholar 

  4. E.G. Paronikyen, A.Kh. Oganesyan, A.S. Noravyan, F.G. Engoyan, F.G. Arsenyan, G.M. Stepanyan, R.G. Paronikyen, R.V. Paronikyen, B.T. Garibdzhanyan, Pharm. Chem. J. 29, 194 (1995)

    Article  Google Scholar 

  5. J.S. New, W.L. Christopher, J.P. Yevich, R. Butler, R. Schlemmer, J. Francis, C.P. VanderMaeln, J.A. Cipollina, J. Med. Chem. 32, 1147 (1989)

    Article  CAS  Google Scholar 

  6. R.D. Bukoski, J. Bo, H. Xue, K. Bian, J. Pharmacol. Exp. Ther. 265, 30 (1993)

    CAS  Google Scholar 

  7. E.G. Paronikyan, A.K. Oganisyan, A.S. Noravyan, R.G. Paronikyan, I.A. Dzhagatspanyan, Pharm. Chem. J. 36, 413 (2002)

    Article  CAS  Google Scholar 

  8. P. Jeschke, A. Harder, W. Etzd, W. Gau, A. Goehrt, J. Benet-Buchholz, G. Thielking, Bioorg. Med. Chem. Lett. 15, 2375 (2005)

    Article  CAS  Google Scholar 

  9. P. Gerster, C. Riegger, M. Fallert, Arzneim. Forsch. 37, 309 (1987)

    CAS  Google Scholar 

  10. D.G. Wishka, D.R. Graber, E.P. Seest, L.A. Dolak, F. Han, W. Watt, J.J. Morris, Org. Chem. 63, 7851 (1998)

    Article  CAS  Google Scholar 

  11. J.L. Marco, M.C. Carreiras, Mini-Rev. Med. Chem. 3, 518 (2003)

    Article  CAS  Google Scholar 

  12. V.S. Dinakaran, K.K. Srinivasan, Der Pharma Chemica 3, 62 (2011)

    CAS  Google Scholar 

  13. M.E. Schnute, R.J. Brideau, S.A. Collier, M.M. Cudahy, T.A. Hopkins, M.L. Knechtel, N.L. Oien, R.S. Sackett, A. Scott, M.L. Stephan, M.W. Wathen, J.L. Wieber, Bioorg. Med. Chem. Lett. 18, 3856 (2008)

    Article  CAS  Google Scholar 

  14. A.J. Buckmelter, L. Ren, E.R. Laird, B. Rast, G. Miknis, S. Wenglowsky, S. Schlachter, M. Welch, E. Tarlton, J. Grina, J. Lyssikatos, B.J. Brandhuber, T. Morales, N. Randolph, G. Vigers, M. Martinson, M. Callejo, Bioorg. Med. Chem. Lett. 21, 1248 (2011)

    Article  CAS  Google Scholar 

  15. R. Tripathy, R.J. McHugh, E.R. Bacon, J.M. Salvino, G. Morton, L.D. Aimone, Z. Huang, J.R. Mathiasen, A. DiCamillo, M.J. Huffman, B.A. McKenna, K. Lu, L.D. Kopec, J. Qian, T.S. Angeles, T. Connors, C. Spais, B. Holskin, E. Duzic, H. Schaffhauser, G.C. Rossé, Bioorg. Med. Chem. Lett. 22, 1421 (2012)

    Article  CAS  Google Scholar 

  16. F.A. Attaby, M.M. Ramla, E.M. Gouda, Phosphorus Sulfur Silicon 182, 517 (2007)

    Article  CAS  Google Scholar 

  17. F.A. Attaby, M.A. Ali, A.H.H. Elghandour, Y.M. Ibrahem, Sulfur Silicon 181, 1 (2006)

    Article  CAS  Google Scholar 

  18. F.A. Attaby, A.H.H. Elghandour, M.A. Ali, Y.M. Ibrahem, Phosphorus Sulfur Silicon 181, 1087 (2006)

    Article  CAS  Google Scholar 

  19. A.E. Amr, M.M. Abdulla, Bioorg. Med. Chem. 14, 4341 (2006)

    Article  CAS  Google Scholar 

  20. W.A. El-Sayed, A.E. Rashad, S.M. Awad, M.M. Ali, Nucleosides, Nucleotides Nucleic Acids 28, 261 (2009)

    Article  CAS  Google Scholar 

  21. H.A. El-Sayed, A.H. Moustafa, A.Z. Haikal, I.M. Abdou, E.S.H. El Ashry, Nucleoside Nucleotide Nucleic Acids 27, 1061 (2008)

    Article  CAS  Google Scholar 

  22. A.H. Moustafa, H.A. Morsy, M.G. Assy, A.Z. Haikal, Nucleoside Nucleotide Nucleic Acids 28, 835 (2009)

    Article  CAS  Google Scholar 

  23. H.A. El-Sayed, A.H. Moustafa, A.Z. Haikal, Phosphorus Sulfur Silicon Relat. Elem. (2012) (in press)

  24. O.M.E. Awad, W.E. Attia, E.S.H. El Ashry, Carbohydr. Res. 339, 469 (2004)

    Article  Google Scholar 

  25. E.S.H. El Ashry, N. Rashed, A.H.S. Shobier, Pharmazie 55, 251 (2000)

    Google Scholar 

  26. E.S.H. El Ashry, N. Rashed, A.H.S. Shobier, Pharmazie 55, 331 (2000)

    Google Scholar 

  27. E.S.H. El Ashry, N. Rashed, A.H.S. Shobier, Pharmazie 55, 403 (2000)

    Google Scholar 

  28. E.S.H. El Ashry, A. El Nemr, Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates (Blackwell, Oxford. UK, 2005)

    Book  Google Scholar 

  29. B. Paul, W. Korytnyk, Carbohydr. Res. 126, 27 (1984)

    Article  CAS  Google Scholar 

  30. C.S. Kuhn, J. Lehmann, J. Steck, Tetrahedron 46, 3129 (1990)

    Article  CAS  Google Scholar 

  31. M. Blane-Muesser, L. Vigne, H. Driguez, J. Lehmann, J. Steck, K. Urbhns, Carbohydr. Res. 224, 59 (1992)

    Article  Google Scholar 

  32. H.A. El-Sayed, A.H. Moustafa, A.Z. Haikal, R. Abu-El-Halawa, E.H. El Ashry, Eur. J. Med. Chem. 46, 2948 (2011)

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding the work through the research group project No. RGP-VPP-0172.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt

    Hassan A. El-Sayed & Said A. Said

  2. Pharmaceutical Chemistry Department, Drug Exploration and Development Chair, College of Pharmacy, King Saud University, Riyadh, 11451, Saudi Arabia

    Abd El-Galil E. Amr

  3. Applied Organic Chemistry Department, National Research Center, El Dokki, Cairo, Egypt

    Abd El-Galil E. Amr

Authors
  1. Hassan A. El-Sayed
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Said A. Said
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Abd El-Galil E. Amr
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Abd El-Galil E. Amr.

Rights and permissions

Reprints and permissions

About this article

Cite this article

El-Sayed, H.A., Said, S.A. & Amr, A.EG.E. Synthesis of some fused heterocyclic systems and their nucleoside candidates. Res Chem Intermed 40, 833–845 (2014). https://doi.org/10.1007/s11164-012-1006-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-1006-y

Keywords

Search

Navigation