Polyamines [Bioactive Small Molecules]

Polyamines are organic compounds having at least two amino groups as part of an otherwise aliphatic chain. The amino groups are usually separated by three or four methylene units, such as putrescine and spermine. Cyclen is the typical example of a class of cyclic polyamines. The polyamines are essential molecules in both eukaryotic and prokaryotic cells, and, therefore, have been isolated from all kinds of living organisms, including humans.^1,2) Especially, the requirement for and the metabolism of polyamines are frequently dysregulated in cancer, and some polyamines can induce diseases caused by neurotoxins.^3,4) Thus, the polyamines, which are available by chemical synthesis, have been attractive for continuing with the study of diseases.^5-10)

References

• 1) Polyaminealkaloids
  • S. Bienz, P. Bisegger, A. Guggisberg, M. Hesse, Nat. Prod. Rep. 2005, 22, 647.
• 2) Defining the Molecular Requirements for the Selective Delivery of Polyamine Conjugates into Cells Containing Active Polyamine Transporters
  • C. Wang, J.-G. Delcros, L. Cannon, F. Konate. H. Carias, J. Biggerstaff, R. A. Gardner, O. Phanstiel IV, J. Med. Chem. 2003, 46, 5129.
• 3) Polyamines and cancer: old molecules, new understanding
  • E. W. Gerner, F. L. Meyskens Jr, Nat. Rev. Cancer 2004, 4, 781.
• 4) Targeting polyamine metabolism and function in cancer and other hyperproliferative diseases
  • R. A. Casero Jr, L. J. Marton, Nat. Rev. Drug Discov. 2007, 6, 373.
• 5) N-Carboalkoxy-2-Nitrobenzenesulfonamides: A Practical Preparation of N-Boc-, N-Alloc-, and N-Cbz-Protected Primary Amines
  • T. Fukuyama, M. Cheung, T. Kan, Synlett 1999, 1301.
• 6) Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-A
  • T. Kan, A. Fujiwara, H. Kobayashi, T. Fukuyama, Tetrahedron 2002, 58, 6267.
• 7) Total synthesis of polyamine toxin HO-416b utilizing the 2-nitrobenzenesulfonamide protecting group
  • Y. Hidai, T. Kan, T. Fukuyama, Tetrahedron Lett. 1999, 40, 4711.
• 8) Total Synthesis of Polyamine Toxin HO-416b and Agel-489 Using a 2-Nitrobenzenesulfonamide Strategy
  • Y. Hidai, T. Kan, T. Fukuyama, Chem. Pharm. Bull. 2000, 48, 1570.
• 9) Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-A
  • T. Kan, A. Fujiwara, H. Kobayashi, T. Fukuyama, Tetrahedron 2002, 58, 6267.
• 10) Application of Odorless Thiols for the Cleavage of 2‐ and 4‐Nitrobenzenesulfonamides
  • M. Matoba, T. Kajimoto, M. Node, Synth. Commun. 2008, 38, 1194.