PDF herunterladen
Synthesis 2008(21): 3433-3442  
DOI: 10.1055/s-0028-1083189
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Studies towards the Development of Psoralen-Acidic Retinoid Conjugates and Hybrids

Maria Militsopoulou, Stavros E. Bariamis, Constantinos M. Athanassopoulos, Dionissios Papaioannou*
Laboratory of Synthetic Organic Chemistry, Department of Chemistry, University of Patras, 26500 Patras, Greece
Fax: +30(261)0997156; e-Mail: dapapaio@chemistry.upatras.gr;
Weitere Informationen

Publikationsverlauf

Received 27 May 2008
Publikationsdatum:
16. Oktober 2008 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The chemical modification of trioxsalen using electrophilic aromatic substitution reactions, followed by either Wittig or Heck reactions or Suzuki coupling, allowed for ready access to C4′ modified trioxsalen derivatives that were successfully used for the preparation of a variety of trioxsalen conjugates with acitretin of either the polyamine or the ester type and trioxsalen-acitretin hybrids.

Key words

electrophilic aromatic substitution - Heck reaction - psoralen-retinoid conjugation - Suzuki coupling - Wittig reaction

    References

  • 1 Van der Kerkhof PCM. Neth. J. Med.  1998,  52:  40 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 2 Krueger G. Ellis CN. J. Am. Acad. Dermatol.  2005,  53:  S94 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 3 Leite VC. Santos RF. Chen LC. Guillo LA. J. Photochem. Photobiol., B  2004,  76:  49 ; and references cited therein
    Google Scholar
  • 4 Gia O. Magno SM. Gonzalez-Diaz H. Quezada E. Santana L. Uriarte E. Via LD. Bioorg. Med. Chem.  2005,  13:  809 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 5 Katz HI. Waalen J. Leach EE. J. Am. Acad. Dermatol.  1999,  41:  S7 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 6 Pilkington T. Brogden RN. Drugs  1992,  43:  597 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 7 Roenigk HH. J. Am. Acad. Dermatol.  1999,  41:  S18 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 8 Van der Kerkhof PCM. Clin. Exp. Dermatol.  2001,  26:  356 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • For a review on PACs see for example:
  • 9a Karygiannis G. Papaioannou D. Eur. J. Org. Chem.  2000,  1841 
    Google Scholar
  • For some recent examples of medicinally interesting PACs see:
  • 9b Camps P. Formosa X. Muñoz-Torrero D. Petrignet J. Badia A. Clos MV. J. Med. Chem.  2005,  48:  1701 
    Google Scholar
  • 9c Cholody WM. Kosakowska-Cholody T. Hollingshead MG. Hariprakasha HK. Michejda CJ. J. Med. Chem.  2005,  48:  4474 
    Google Scholar
  • 9d Nagarajan M. Morrell A. Antony S. Kohlhagen G. Agama K. Pommier Y. Ragazzon PA. Garbett NC. Chaires JB. Hollingshead M. Cushman M. J. Med. Chem.  2006,  49:  5129 
    Google Scholar
  • 9e Oves D. Fernández S. Verlinden L. Bouillon R. Verstuyf A. Ferrero M. Gotor V. Bioorg. Med. Chem.  2006,  14:  7512 
    Google Scholar
  • 9f Battaglia A. Guerrini A. Baldelli E. Fontana G. Varchi G. Samori C. Bombardelli E. Tetrahedron Lett.  2006,  47:  2667 
    Google Scholar
  • 9g Wu D. Ji S. Wu Y. Ju Y. Zhao Y. Bioorg. Med. Chem. Lett.  2007,  17:  2983 
    Google Scholar
  • For the recent development of an α-methylene-γ-butyrolactone-psoralen bisamide heterodimer see:
  • 9h Ropp S. Guy J. Berl V. Bischoff P. Lepoittevin J.-P. Bioorg. Med. Chem.  2004,  12:  3619 
    Google Scholar
  • For a recent example of an EC prodrug see:
  • 10a Zakharian TY. Seryshev A. Sitharaman B. Gilbert BE. Knight V. Wilson BE. J. Am. Chem. Soc.  2005,  127:  12508 
    Google Scholar
  • See also:
  • 10b Walsh JJ. Coughlan D. Heneghan N. Gaynor C. Bell A. Bioorg. Med. Chem. Lett.  2007,  17:  3599 
    Google Scholar
  • 11 Tietze LF. Bell HP. Chandrasekhar S. Angew. Chem. Int. Ed.  2003,  42:  3996 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 12 Papaioannou D, Drainas D, and Tsambaos D. inventors; WO  2004,018,001.  ; Chem. Abstr. 2004, 140, 235912
  • 13a Isaacs ST. Shen C.-KJ. Hearst JE. Rapoport H. Biochemistry  1977,  16:  1058 
    Google Scholar
  • 13b Kim K. Matsuura K. Kimizuka N. Bioorg. Med. Chem.  2007,  15:  4311 
    Google Scholar
  • For selected examples of other psoralen derivatives, their synthesis and mode of action, see ref. 4 above and:
  • 14a Oliveira AMAG. Raposo MMM. Oloveira-Campos AMF. Machado AEH. Puapairoj P. Pedro M. Nascimento MSJ. Portela C. Afonso C. Pinto M. Eur. J. Med. Chem.  2006,  41:  367 
    Google Scholar
  • 14b Chimichi S. Boccalini M. Cosimelli B. Viola G. Vedaldi D. Dall’Acqua F. Tetrahedron  2002,  58:  4859 
    Google Scholar
  • 14c Traven VF. Kravtcenko DV. Chibisova TA. Shorshnev SV. Eliason R. Wakefield DH. Heterocycl. Commun.  1996,  2:  345 
    Google Scholar
  • 14d Besson T. Ruiz N. Coudert G. Guillaumet G. Tetrahedron  1995,  51:  3197 
    Google Scholar
  • 14e Bisagni E. J. Photochem. Photobiol., B  1992,  14:  23 ; and references cited therein
    Google Scholar
  • 14f Zubía E. Luis FR. Massanet GM. Collado IG. Tetrahedron  1992,  48:  4239 
    Google Scholar
  • 14g Confalone PN. Confalone DL. Tetrahedron  1981,  37:  1265 
    Google Scholar
  • 15 Gaernter R. J. Am. Chem. Soc.  1952,  74:  5319 
    CrossrefGoogle Scholar
  • 16 Isaacs ST. Rapoport H. Hearst JE. J. Labelled Compd. Radiopharm.  1982,  XIX:  345 
    CrossrefGoogle Scholar
  • 17 Lambertin F. Wende M. Quirin MJ. Taran M. Delmond B. Eur. J. Org. Chem.  1999,  1489 
    CrossrefGoogle Scholar
  • 18 Travis RB. Sivakumar M. Olatunji Hollist G. Borhan B. Org. Lett.  2003,  5:  1031 
    CrossrefGoogle Scholar
  • 19 Kaufman KD. Worden LR. Lode ET. Strong MK. Reitz NC. J. Org. Chem.  1970,  35:  157 
    CrossrefGoogle Scholar
  • 20 Farrar MW. Levine R. J. Am. Chem. Soc.  1950,  72:  4433 
    CrossrefGoogle Scholar
  • 21a Ziegler CB. Heck RF. J. Org. Chem.  1978,  43:  2941 
    Google Scholar
  • 21b Mikroyiannidis JA. Yu Y.-J. Lee S.-H. Jin J.-I. J. Polym. Sci., Part A: Polym. Chem.  2006,  44:  4494 
    Google Scholar
  • 22 Bryan DB. Hall RF. Holden KG. Huffman WF. Gleason JG. J. Am. Chem. Soc.  1977,  99:  2353 
    CrossrefPubMedGoogle Scholar
  • 23 Trippett S. Walker DM. J. Chem. Soc.  1961,  1266 
    Google Scholar
  • 24 Rafecas Jané L, Riera Escalé A, Écija Queralt M, Moyano Baldoire A, Comely A, and Casalprim Castellà I. inventors; WO  2006,067,216.  ; Chem. Abstr. 2006, 145, 103949
  • 25 Geall AJ. Blagbrough IS. Tetrahedron  2000,  56:  2449 
    CrossrefGoogle Scholar