Design and synthesis of macrocyclic polyoxazoles

Abstract

Two macrocyclic polyoxazoles with different sizes and numbers of side chains were designed and synthesized from the linear-type precursors obtained by the iterative application of oxazole formation reaction via effective trimerization or dimerization respectively under highly diluted conditions in one pot.

Keywords

Telomerase / Telomestatin / G-Quadruplex / Macrocyclic compound / Polyoxazole

References

[1] Oganesian L, Bryan T M. BioEssays, 2007, 29(2): 155.

[2] le Toung V T, Han S, Chae J, Park H J. Curr. Pharm. Des., 2012, 18: 1948.

[3] Tarkanyi I, Aradi J. Biochimie, 2008, 90(1): 156.

[4] Kelland L R. Eur. J. Cancer, 2005, 41(7): 971.

[5] Folini M, Gandellini P, Zaffaroni N. Biochim. Biophys. Acta. Mol. Basis. Dis., 2009, 1792(4): 309.

[6] Iida K, Tsubouchi G, Nakamura T, Majima S, Seimiya H, Nagasawa K. Med. Chem. Commun., 2013, 4(1): 260.

[7] Parkinson G N, Lee M P, Neidle S. Nature, 2002, 417(6891): 876.

[8] Xu Y, Noguchi Y, Sugiyama H. Bioorg. Med. Chem., 2006, 14(16): 5584.

[9] Ambrus A. Nucleic Acids Res., 2006, 34(9): 2723.

[10] Wang Y, Patel D J. Structure, 1993, 1(4): 263.

[11] Kim N W, Piatyszek M A, Prowse K R, Harley C B, West M D, Ho P L C, Coviello G M, Wright W E, Weinrich S L, Shay J W. Science, 1994, 266(5193): 2011.

[12] Hiyama K, Hirai Y, Kyoizumi S, Akiyama M, Hiyama E, Piatyszek M A, Shay J W, Ishioka S, Yamakido M. J. Immunol., 1995, 155(8): 3711.

[13] Wright W E, Piatyszek M A, Rainey W E, Byrd W, Shay J W. Dev. Genet., 1996, 18(2): 173.

[14] Cong Y S, Wright W E, Shay J W. Microbiol. Mol. Biol. R., 2002, 66(3): 407.

[15] Lustig A J. Nat. Rev. Genet., 2003, 4(11): 916.

[16] Mergny J L, Riou J F, Mailliet P, Teulade-Fichou M P, Gilson E. Nucleic Acids Res., 2002, 30(4): 839.

[17] Vega L R, Mateyak M K, Zakian V A. Nat. Rev. Mol. Cell. Bio., 2003, 4(12): 948.

[18] Shay J, Bacchetti S. Eur. J. Cancer, 1997, 33(5): 787.

[19] Sun C W, Wang J, Pang C C, Li J, Xiao D. Chem. Res. Chinese Universities, 2013, 29(6): 1104.

[20] Zhang X L, Liu A L, Zhao Y, Xiong L X, Li Z M. Chem. Res. Chinese Universities, 2013, 29(6): 1134.

[21] Shin-ya K, Wierzba K, Matsuo K I, Ohtani T, Yamada Y, Furihata K, Hayakawa Y, Seto H. J. Am. Chem. Soc., 2001, 123(6): 1262.

[22] Kim M Y, Vankayalapati H, Shin-ya K, Wierzba K, Hurley L H. J. Am. Chem. Soc., 2002, 124(10): 2098.

[23] Tahara H, Shin-ya K, Seimiya H, Yamada H, Tsuruo T, Ide T. Oncogene, 2005, 25(13): 1955.

[24] Tauchi T, Shin-ya K, Sashida G, Sumi M, Okabe S, Ohyashiki J H, Ohyashiki K. Oncogene, 2006, 25(42): 5719.

[25] Gomez D, Wenner T, Brassart B, Douarre C, O’Donohue M F, El Khoury V, Shin-ya K, Morjani H, Trentesaux C, Riou J F. J. Biol. Chem., 2006, 281(50): 38721.

[26] Doi T, Yoshida M, Shin-ya K, Takahashi T. Org. Lett., 2006, 8(18): 4165.

[27] Minhas G S, Pilch D S, Kerrigan J E, LaVoie E J, Rice J E. Bioorg. Med. Chem. Lett., 2006, 16(15): 3891.

[28] Tera M, Ishizuka H, Takagi M, Suganuma M, Shin-ya K, Nagasawa K. Angew. Chem. Int. Ed., 2008, 47(30): 5557.

[29] Rzuczek S G, Pilch D S, la Voie E J, Rice J E. Bioorg. Med. Chem. Lett., 2008, 18(3): 913.

[30] Hernandez D, Riego E, Albericio F, Alvarez M. Eur. J. Org. Chem., 2008, 3389.

[31] Tera M, Lida K, Ishizuka H, Takagi M, Suganuma M, Doi T, Shin-ya K, Nagasawa K. ChemBioChem, 2009, 10(3): 431.

[32] Iida K, Tera M, Hirokawa T, Shin-ya K, Nagasawa K. Chem. Comm., 2009, 6481.

[33] Rzuczek S G, Pilch D S, Liu A, Liu L, la Voie E J, Rice J E. J. Med. Chem., 2010, 53(9): 3632.

[34] Majima S, Tera M, Iida K, Shin-ya K, Nagasawa K. Heterocycles, 2011, 82(2): 1345.

[35] Linder J R, Garner T P, Williams H E L, Searle M S, Moody C J. J. Am. Chem. Soc., 2011, 133(4): 1044.

[36] Nagasawa K, Iida K, Majima S, Ohtake T, Tera M, Shin-ya K. Heterocycles, 2012, 84(1): 401.

[37] Tera M, Sohtome Y, Ishizuka H, Doi T, Takagi M, Kazuo S Y, Nagasawa K. Heterocycles, 2006, 69(1): 505.

[38] Han F S, Osajima H, Cheung M, Tokuyama H, Fukuyama T. Chem. Comm., 2006, 1757.

[39] Han F S, Osajima H, Cheung M, Tokuyama H, Fukuyama T. Chem. Eur. J., 2007, 13(11): 3026.

[40] Han F S, Tokuyama H, Fukuyama T. Chem. Comm., 2007, 3444.

[41] Yamada T, Okumura K, Yonezawa Y, Shin C G. Chem. Lett., 2001, 30(2): 102.

[42] Tavares F, Lawson J P, Meyers A I. J. Am. Chem. Soc., 1996, 118(13): 3303.

[43] Marson C M, Saadi M. Org. Biomol. Chem., 2006, 4(21): 3892.