Mild and Efficient Synthesis of N¹,N⁵,N¹⁰-Tri-tert-butoxycarbonyl Spermine

REFERENCES

• Kuksa , V. ; Buchan , R. ; Lin , P. K. T. Synthesis of polyamines, their derivatives, analogues, and conjugates . Synthesis 2000 , 1189 – 1207 .
   Web of Science ®Google Scholar
• Brret , J. M. ; Kruczynski , A. ; Viapé , S. ; Annereau , J. P. ; Brel , V. ; Guminski , Y. ; Delcros , J. G. ; Lansiaux , A. ; Guilbaud , N. ; Imbert , T. ; Bailly , C. F14512, a potent antitumor agent targeting topoisomerase II vectored into cancer cells via the polyamine transport system . Cancer Res. 2008 , 68 , 9845 – 9853 .
   PubMed Web of Science ®Google Scholar
• Blagbrough , I. S. ; Hadithi , D. A. ; Geall , A. J. Cheno-, urso- and deoxycholic acid spermine conjugates: Relative binding affinities for calf thymus DNA . Tetrahedron 2000 , 56 , 3439 – 3447 .
   Web of Science ®Google Scholar
• Battaglia , A. ; Guerrini , A. ; Baldelli , E. ; Fontana , G. ; Varchi , G. ; Samori , C. ; Bombardelli , E. Synthesis of 7- and 10-spermine conjugates of paclitaxel and 10-deacetyl-paclitaxel prodrugs . Tetrahedron Lett. 2006 , 47 , 2667 – 2670 .
   Web of Science ®Google Scholar
• Geall , A. J. ; Blagbrough , I. S. Homologation of polyamines in the rapid synthesis of lipospermine conjugates and related lipoplexes . Tetrahedron 2000 , 56 , 2449 – 2460 .
   Web of Science ®Google Scholar
• Bueno , G. J. ; Klimkait , T. ; Gilberta , I. H. ; Simonsa , C. Solid-phase synthesis of diamine and polyamine amino acid derivatives as HIV-1 Tat-TAR binding inhibitors . Bioorg. Med. Chem. 2003 , 11 , 87 – 94 .
   PubMed Web of Science ®Google Scholar
• Dallavalle , S. ; Giannini , G. ; Alloatti , D. ; Casati , A. ; Marastoni , E. ; Musso , L. ; Merlini , L. ; Morini , G. ; Penco , S. ; Pisano , C. ; Tinelli , S. ; Cesare , M. D. ; Beretta , G. L. ; Zunino , F. Synthesis and cytotoxic activity of polyamine analogues of camptothecin . J. Med. Chem. 2006 , 49 , 5177 – 5186 .
   PubMed Web of Science ®Google Scholar
• Winkler , J. ; Saadat , K. ; Gavilán , M. D. ; Urban , E. ; Noe , C. R. Oligonucleotide-polyamine conjugates: Influence of length and position of 2′-attached polyamines on duplex stability and antisense effect . Eur. J. Med. Chem. 2009 , 44 , 670 – 677 .
   PubMed Web of Science ®Google Scholar
• Caser , Jr. , R. A. ; Woster , P. M. Recent advances in the development of polyamine analogues as antitumor agents . J. Med. Chem. 2009 , 52 , 4551 – 4573 .
   PubMed Web of Science ®Google Scholar
• Geall , A. J. ; Blagbrough , I. S. Homologation of polyamines in the synthesis of lipo-spermine conjugates and related lipoplexes . Tetrahedron Lett. 1998 , 39 , 443 – 446 .
   Web of Science ®Google Scholar
• Blagbrough , I. S. ; Geall , A. J. Practical synthesis of unsymmetrical polyamine amides . Tetrahedron Lett. 1998 , 39 , 439 – 442 .
   Web of Science ®Google Scholar
• Wellendorph , P. ; Jaroszewski , J. W. ; Hansen , S. H. ; Franzyk , H. A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues . Eur. J. Med. Chem. 2003 , 38 , 117 – 122 .
   PubMed Web of Science ®Google Scholar
• Jasys , V. J. ; Kelbaugh , P. R. ; Nason , D. M. ; Phillips , D. ; Rosnack , K. J. ; Saccomano , N. A. ; Stroh , J. G. ; Volkmann , R. A. Isolation, structure elucidation, and synthesis of novel hydroxylamine-containing polyamines from the venom of the Agelenopsis aperta spider . J. Am. Chem. Soc. 1990 112 , 6696 – 6704 .
   Web of Science ®Google Scholar
• Sata , N. U. ; Sugano , M. ; Matsunaga , S. ; Fusetani , N. Sinulamide: An H, K-ATPase inhibitor from a soft coral . Sinularia sp. Tetrahedron Lett. 1999 , 40 , 719 .
   Web of Science ®Google Scholar