Download PDF
Synthesis 2010(14): 2451-2455  
DOI: 10.1055/s-0029-1218781
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Novel Chlorin e 6 Derivatives Containing Organophosphorus Groups

Lidiya I. Minaevaa, Maria M. Kabachnik*a, Gelii V. Ponomarevb, Julia V. Morozovab, Irina P. Beletskayaa
a Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119992, Russian Federation
e-Mail: mariamk@mail.ru;
b Orekhovich Institute of Biomedical Chemistry, Russian Academy of Medical Science, Pogodinskaya St. 10, Moscow 119121, Russian Federation
Further Information

Publication History

Received 12 March 2010
Publication Date:
10 May 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

New types of chlorin e 6 derivatives containing organophosphorus units were synthesized under microwave irradiation.

Key words

phosphorylations - antitumor agents - photodynamic therapy - amino phosphonates - phosphoramidates - bisphosphonates - chlorin e 6

    References

  • 1a Nyman ES. Hynninen PH. J. Photochem. Photobiol., B  2004,  73:  1 
    Google Scholar
  • 1b Haeubl M. Schuerz S. Svejda B. Reith LM. Gruber B. Pfragner R. Schoefberger W. Eur. J. Med. Chem.  2010,  45:  760 
    Google Scholar
  • 2a Renno RZ. Miller JW. Adv. Drug Delivery Rev.  2001,  52:  63 
    Google Scholar
  • 2b Hayashi K. Ohno-Matsui K. Teramukai T. Shimada N. Moriyama M. Hara W. Yoshida T. Tokoro T. Mochizuki M. J. Mol. Struct.  2008,  875:  167 
    Google Scholar
  • 2c Tajiri H. Yokoyama K. Boku N. Ohtsu A. Fujii T. Yoshida S. Sato T. Hakamata K. Hayashi K. Sakata I. Cancer Lett.  1997,  111:  215 
    Google Scholar
  • 3a Mody TD. J. Porphyrins Phthalocyanines  2000,  4:  362 
    Google Scholar
  • 3b Ali H. van Lier JE. Chem. Rev.  1999,  99:  2379 
    Google Scholar
  • 3c Pandey RK. J. Porphyrins Phthalocyanines  2000,  4:  368 
    Google Scholar
  • 4a Wainwright M. Anti-Cancer Agents Med. Chem.  2008,  8:  820 
    Google Scholar
  • 4b Robertson CA. Hawkins Evans D. Abrahamse H. J. Photochem. Photobiol., B  2009,  96:  1 
    Google Scholar
  • 5 Shternberg ED. Dolfin D. Brukner C. Tetrahedron  1998,  54:  4151 
    CrossrefGoogle Scholar
  • 6a Ol’shevskaya VA. Savchenko AN. Zaitsev AV. Kononova EG. Petrovskii PV. Ramonova AA. Tatarskiy VV. Uvarov OV. Moisenovich MM. Kalinin VN. Shtil AA. J. Organomet. Chem.  2009,  694:  1632 
    Google Scholar
  • 6b Giard D. Weagle G. Gupta A. Berube G. Chapados C. Bioorg. Med. Chem. Lett.  2008,  18:  360 
    Google Scholar
  • 6c Belykh DV. Tarabukina IS. Gruzdev IV. Kutchin AV. Mendeleev Commun.  2007,  17:  340 
    Google Scholar
  • 7a Szurko A. Rams M. Sochanik A. Sieroń-Stotny K. Kozielec AM. Montforts F.-P. Wrzalik R. Ratuszna A. Bioorg. Med. Chem.  2009,  17:  8197 
    Google Scholar
  • 7b Bregadze VI. Sivaev IB. Lobanova IA. Titeev RA. Brittal DI. Grin MA. Mironov AF. Appl. Radiat. Isot.  2009,  67:  S101 
    Google Scholar
  • 7c Smith KM. Bisset GMF. Bushell MJ.
    J. Org. Chem.  1980,  45:  2218 
    Google Scholar
  • 7d Pandey SK. Zheng X. Morgan J. Missert JR. Liu T.-H. Shibata M. Bellnier DA. Oseroff AR. Henderson BW. Dougherty TJ. Pandey RK. Mol. Pharmaceutics  2007,  4:  448 
    Google Scholar
  • 8a Hu D.-Y. Wan Q.-Q. Yang S. Song B.-A. Bhadury PS. Jin L.-H. Yan K. Liu F. Chen Z. Xue W. J. Agric. Food Chem.  2008,  56:  998 
    Google Scholar
  • 8b Wittine K. Benci K. Rajić Z. Zorc B. Kralj M. Marjanović M. Pavelić K. De Clercq E. Andrei G. Snoeck R. Balzarini J. Mintas M. Eur. J. Med. Chem.  2009,  44:  143 
    Google Scholar
  • 8c Zlatev I. Giraut A. Morvan F. Herdewijn P. Vasseur J.-J. Bioorg. Med. Chem.  2009,  17:  7008 
    Google Scholar
  • 8d Morioka M. Kamizono A. Takikawa H. Mori A. Ueno H. Kadowaki S. Nakao Y. Kato K. Umezawa K. Bioorg. Med. Chem.  2010,  18:  1143 
    Google Scholar
  • 9a Kabachnik MI. Medved TYa. Dokl. Akad. Nauk SSSR  1952,  689 ; Chem. Abstr. 1953, 47, 2724b
    Google Scholar
  • 9b Fields EK. J. Am. Chem. Soc.  1952,  74:  1528 
    Google Scholar
  • 10a Ranu BC. Hajra A. Jana U. Org. Lett.  1999,  1:  1141 
    Google Scholar
  • 10b Chandrasekhar S. Prakash SJ. Jagadeshwar V. Narsihmulu C. Tetrahedron Lett.  2001,  42:  5561 
    Google Scholar
  • 10c Qian C. Huang T. J. Org. Chem.  1998,  63:  4125 
    Google Scholar
  • 11a Kabachnik MM. Zobnina EV. Beletskaya IP. Synlett  2005,  1393 
    Google Scholar
  • 11b Kabachnik MM. Zobnina EV. Pavlov VYa. Konstantinov IO. Beletskaya IP. Russ. Chem. Bull.  2005,  54:  262 ; Chem. Abstr. 2006, 144, 432906
    Google Scholar
  • 11c Yashin NV. Villemson EV. Chemagin AV. Averina EB. Kabachnik MM. Kuznetsova TS. Synthesis  2008,  464 
    Google Scholar
  • 11d Kabachnik MM. Minaeva LI. Beletskaya IP. Synthesis  2009,  2357 
    Google Scholar
  • 12 Atherton FR. Openshaw HT. Todd RR. J. Chem. Soc.  1945,  660 
    CrossrefGoogle Scholar
  • 13 Minaeva LI. Patrikeeva LS. Orlinson BS. Novakov IA. Kabachnik MM. Beletskaya IP. Russ. J. Org. Chem.  2010,  46:  172 
    Google Scholar
  • 14a Takeuchi M. Sakamoto S. Yoshida M. Abe T. Isomura Y. Chem. Pharm. Bull.  1993,  41:  688 
    Google Scholar
  • 14b Kotsikorou E. Song Y. Chan JMW. Faelens S. Tovian Z. Broderick E. Bakalara R. Docampo R. Oldfield E. J. Med. Chem.  2005,  48:  6128 
    Google Scholar