Skip to main content

Advertisement

SpringerLink
Log in

Applications of triphenylpyrylium salt-sensitized electron-transfer photo-oxygenation reactions to the synthesis of benzo-fused 1,4-diaryl-2,3-dioxabicyclo[2.2.2]octanes as new antimalarial cyclic peroxides

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

Abstract

Benzo-fused 1,4-diaryl-2,3-dioxabicyclo[2.2.2]octanes 4a–d (4a: Ar = C6H5, 4b: Ar = p-FC6H4, 4c: Ar = p-MeC6H4, 4d: Ar = p-MeOC6H4) were synthesized by 2,4,6-triphenylpyrylium tetrafluoroborate (TPPBF4)-sensitized photoinduced electron-transfer (PET)-promoted oxygenation reactions, and their in-vitro antimalarial activity was evaluated. The results showed that these substances have sufficiently high activity to enable them to serve as antimalarial lead compounds. In addition, TPPBF4-biphenyl-cosensitized PET oxygenation was shown to be an efficient method for introduction of an O–O moiety in the construction of antimalarial cyclic peroxides.

Graphical Abstract

New antimalarial bicyclic peroxides 4 were synthesized by TPPBF4-sensitized photoinduced electron-transfer oxygenation reactions.

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

Similar content being viewed by others

References

  1. S.R. Meshnick, C.W. Jefford, G.H. Posner, M.A. Avery, W. Peters, Parasitol Today 12, 79–82 (1996). and references cited therein

    Article  CAS  Google Scholar 

  2. K.J. McCullough, M. Nojima, Curr. Org. Chem. 5, 601–636 (2001)

    Article  CAS  Google Scholar 

  3. A.J. Bloodworth, T. Hagen, K.A. Johnson, I. Lenoir, C. Moussy, Tetrahedron Lett. 38, 635–638 (1997)

    Article  CAS  Google Scholar 

  4. P.M. O’Neil, L.P. Bishop, N.L. Searle, J.L. Maggs, S.A. Ward, P.G. Bray, R.C. Storr, B.K. Park, Tetrahedron Lett. 38, 4263–4266 (1997)

    Article  Google Scholar 

  5. Y. Takaya, K. Kurumada, Y. Takeuji, H.-S. Kim, Y. Shibata, N. Ikemoto, Y. Wataya, Y. Ohshima, Tetrahedron Lett. 39, 1361–1364 (1997)

    Article  Google Scholar 

  6. H.-S. Kim, Y. Shibata, Y. Wataya, K. Tsuchiya, A. Masuyama, M. Nojima, J. Med. Chem. 42, 2604–2609 (1999)

    Article  CAS  Google Scholar 

  7. H.-S. Kim, Y. Nagai, K. Ono, K. Begum, Y. Wataya, Y. Hamada, K. Tsuchiya, A. Masuyama, M. Nojima, K.J. McCullough, J. Med. Chem. 44, 2357–2361 (2001)

    Article  CAS  Google Scholar 

  8. S.H. Hindley, S.A. Ward, R.C. Storr, N.L. Searle, P.G. Bray, B.K. Park, J. Davies, P.M. O’Neil, J. Med. Chem. 45, 1052–1063 (2002)

    Article  CAS  Google Scholar 

  9. Y. Hamada, H. Tokuhara, A. Masuyama, M. Nojima, H.-S. Kim, K. Ono, N. Ogura, Y. Wataya, J. Med. Chem. 45, 1374–1378 (2002). and references cited therein

    Article  CAS  Google Scholar 

  10. G.H. Posner, X. Tao, J.N. Cumming, D. Klinedinst, T.A. Shapiro, Tetrahedron Lett. 37, 7225–7228 (1996)

    Article  CAS  Google Scholar 

  11. G.H. Posner, D. Wang, L. Gonzares, X. Tao, J.N. Cumming, D. Klinedinst, T.A. Shapiro, Tetrahedron Lett. 37, 815–818 (1996)

    Article  CAS  Google Scholar 

  12. G.H. Posner, L. Gonzares, J.N. Cumming, D. Klinedinst, T.A. Shapiro, Tetrahedron 53, 37–50 (1997)

    Article  CAS  Google Scholar 

  13. M. Kamata, T. Kudoh, J. Kaneko, H.-S. Kim, Y. Wataya, Tetrahedron Lett. 43, 617–620 (2002)

    Article  CAS  Google Scholar 

  14. M. Kamata, C. Satoh, H.-S. Kim, Y. Wataya, Tetrahedron Lett. 43, 8313–8317 (2002)

    Article  CAS  Google Scholar 

  15. Y. Takahashi, K. Wakamatsu, S. Morishima, T. Miyashi, J. Chem. Soc. Perkin Trans. 2, 243–253 (1993)

    Article  Google Scholar 

  16. M. Suzuki, H. Ohtake, Y. Kameya, N. Hamanaka, R. Noyori, J. Org. Chem. 54, 5292–5302 (1989)

    Article  CAS  Google Scholar 

  17. M. Kamata, M. Ohta, K. Komatsu, H.-S. Kim, Y. Wataya, Tetrahedron Lett. 44, 2063–2067 (2002)

    Article  Google Scholar 

  18. M. Kamata, K. Murayama, T. Miyashi, Tetrahedron Lett. 31, 4129–4132 (1989)

    Article  Google Scholar 

  19. M. Kamata, K. Murayama, T. Miyashi, J. Chem. Soc., Chem. Commun. 828–829 (1990)

  20. M. Kamata, Y. Kato, E. Hasegawa, Tetrahedron Lett. 32, 4349–4352 (1991)

    Article  CAS  Google Scholar 

  21. M. Kamata, H. Otogawa, E. Hasegawa, Tetrahedron Lett. 32, 7421–7424 (1991)

    Article  CAS  Google Scholar 

  22. M. Kamata, M. Sato, E. Hasegawa, Tetrahedron Lett. 33, 5085–5088 (1992)

    Article  CAS  Google Scholar 

  23. M. Kamata, Y. Murakami, Y. Tamagawa, M. Kato, E. Hasegawa, Tetrahedron 45, 12821–12828 (1994)

    Article  Google Scholar 

  24. M. Kamata, Y. Yokoyama, N. Karasawa, M. Kato, E. Hasegawa, Tetrahedron Lett. 37, 3483–3486 (1996)

    Article  CAS  Google Scholar 

  25. M. Kamata, S. Nagai, M. Kato, E. Hasegawa, Tetrahedron Lett. 37, 7779–7782 (1996)

    Article  CAS  Google Scholar 

  26. M. Kamata, K. Komatsu, R. Akaba, Tetrahedron Lett. 42, 9203–9206 (2001)

    Article  CAS  Google Scholar 

  27. Y. Takahashi, Y. Ohya, H. Ikeda, T. Miyashi, J. Chem. Soc. Chem. Commun 38, 1749–1750 (1995)

    Article  Google Scholar 

  28. H. Ikeda, T. Ikeda, M. Akagi, H. Namai, T. Miyashi, Y. Takahashi, M. Kamata, Tetrahedron Lett. 46, 1831–1835 (2005)

    Article  CAS  Google Scholar 

  29. W.Y. Lee, B.G. Moon, C.-H. Park, S.-H. Bang, J.H. Lee, Bull. Korean Chem. Soc. 9, 325–328 (1988)

    CAS  Google Scholar 

  30. M.A. Miranda, H. Garcia, Chem. Rev. 94, 1063–1089 (1994). and references cited therein

    Article  CAS  Google Scholar 

  31. D. Rehm, A. Weller, Isr. J. Chem. 8, 259 (1970)

    CAS  Google Scholar 

  32. M.A. Fox, M. Chanon (eds.), Photoinduced Electron Transfer (Elsevier, Amsterdam, 1988). Parts A-D

    Google Scholar 

  33. P.S. Mariano, (ed.), Advances in Electron Transfer Chemistry, vol. 1–6 (JAI Press, Greenwich, 1991–1999)

  34. V. Balzani (ed.), Electron Transfer in Chemistry (vols. 1–5) (WILEY-VCH, Weinheim, 2001)

    Google Scholar 

  35. A.P. Schaap, S. Siddiqui, G. Prasad, E. Palomino, M. Sandison, Tetrahedron 41, 2229–2235 (1985)

    Article  CAS  Google Scholar 

  36. A.P. Schaap, L. Lopez, S.D. Gagnon, J. Am. Chem. Soc. 105, 663–664 (1983)

    Article  CAS  Google Scholar 

  37. A.P. Schaap, S. Siddiqui, S.D. Gagnon, L. Lopez, J. Am. Chem. Soc. 105, 5149–5150 (1983)

    Article  CAS  Google Scholar 

  38. A.P. Schaap, L. Lopez, S.D. Anderson, S.D. Gagnon, Tetrahedron Lett. 22, 5493–5496 (1982)

    Article  Google Scholar 

  39. T. Miyashi, H. Ikeda, A. Konno, O. Okitsu, Y. Takahashi, Pure Appl. Chem. 62, 1531–1538 (1990)

    Article  CAS  Google Scholar 

  40. A.G. Griesbeck, O. Sadlek, K. Polborn, Liebigs Ann. 4, 545–549 (1996)

    Google Scholar 

  41. Y. Takahashi, O. Okitsu, M. Ando, T. Miyashi, Tetrahedron Lett. 35, 3953–3956 (1994)

    Article  CAS  Google Scholar 

  42. M. Kamata, J. Kaneko, J. Hagiwara, R. Akaba, Tetrahedron Lett. 45, 7423–7428 (2004)

    Article  CAS  Google Scholar 

  43. R. Akaba, H. Sakuragi, K. Tokumaru, J. Chem. Soc. Perkin Trans. 2, 291–297 (1991)

    Google Scholar 

  44. G. Haucke, P. Czerney, F. Cebulla, Ber. Bunsen-Ges. Phys. Chem. 96, 880–886 (1992)

    CAS  Google Scholar 

  45. S.L. Mattes, S. Farid, Acc. Chem. Res. 15, 80–86 (1982)

    Article  CAS  Google Scholar 

  46. S.L. Mattes, S. Farid, in Organic Photochemistry (Vol. 6, Chap. 4), ed. by A. Padwa (New York, Marcel Dekker, 1983)

    Google Scholar 

  47. R. Akaba, S. Aihara, H. Sakuragi, K. Tokumaru, J. Chem. Soc. Chem. Commun. 109, 1262 (1987)

    Article  Google Scholar 

  48. I.R. Gould, D. Ege, J.E. Moser, S. Farid, J. Am. Chem. Soc. 112, 4290–4301 (1990). and references cited therein

    Article  CAS  Google Scholar 

  49. L.E. Marning, C. Gu, C.S. Foote, J. Phys. Chem. 87, 40–44 (1983)

    Article  Google Scholar 

  50. J. Santamaria, Tetrahedron Lett. 22, 4511–4514 (1981)

    Article  CAS  Google Scholar 

  51. M. Kamata, Y. Nishikata, M. Kato, J. Chem. Soc. Chem. Commun. 20, 2047–2048 (1996)

    Google Scholar 

  52. J.A. VanAllan, G.A. Reynolds, J. Org. Chem. 33, 1102–1105 (1968)

    Article  CAS  Google Scholar 

  53. W. Trager, J.B. Jensen, Science 193, 673–675 (1976)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge financial support provided by The Uchida Energy Science Promotion Foundation. We also thank Professor Eietsu Hasegawa (Department of Chemistry, Faculty of Science, Niigata University), Professor Ryoichi Akaba (Department of Chemistry, Gunma College of Technology), Professor Tsutomu Miyashi (Department of Chemistry, Graduate School of Science, Tohoku University), Professor Yasutake Takahashi (Graduated School of Medicine and Pharmaceutical Science for Education, University of Toyama), and Professor Hiroshi Ikeda (Department of Chemistry, Graduate School of Engineering, Osaka Prefecture University) for their helpful comments and assistance.

Author information

Authors and Affiliations

  1. Faculty of Education, Department of Chemistry, Niigata University, Ikarashi, Niigata, 950-2181, Japan

    Masaki Kamata, Jun-ichi Hagiwara, Tomoko Hokari, Chiharu Suzuki, Ryohta Fujino & Sayaka Kobayashi

  2. Faculty of Pharmaceutical Sciences, Division of International Infectious Diseases Control, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Tsushima Naka 1-1-1 Kita-Ku, Okayama City, 700-8530, Okayama, Japan

    Hye-Sook Kim & Yusuke Wataya

Authors
  1. Masaki Kamata
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jun-ichi Hagiwara
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tomoko Hokari
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Chiharu Suzuki
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ryohta Fujino
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Sayaka Kobayashi
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Hye-Sook Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Yusuke Wataya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Masaki Kamata.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kamata, M., Hagiwara, Ji., Hokari, T. et al. Applications of triphenylpyrylium salt-sensitized electron-transfer photo-oxygenation reactions to the synthesis of benzo-fused 1,4-diaryl-2,3-dioxabicyclo[2.2.2]octanes as new antimalarial cyclic peroxides. Res Chem Intermed 39, 127–137 (2013). https://doi.org/10.1007/s11164-012-0637-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0637-3

Keywords

Search

Navigation