Solution phase synthesis of amyloid-cleaving catalysts, two [1,3,5]triazine based compounds

Keunhong Jeong; Min Kyum Kim; Woo Young Chung; Young Sik Kye; Ji-Hyun Kim; Junghun Suh

Journal of Industrial and Engineering Chemistry, Vol.15, No.3, 342-347, May, 2009

DOI10.1016/j.jiec.2008.12.010 Export Citation

Solution phase synthesis of amyloid-cleaving catalysts, two [1,3,5]triazine based compounds

Keunhong Jeong, Min Kyum Kim¹, Woo Young Chung, Young Sik Kye, Ji-Hyun Kim, and Junghun Suh^{1, †}

Department of Chemistry, Korea Military Academy, Seoul 139-799, South Korea
¹Department of Chemistry, Seoul National University, Seoul 151-747, South Korea

E-mail:

Solution phase synthetic method for amyloid-cleaving catalysts was developed, which bears triazine core, scaffold with bulky and that have various solubility properties; Co(III) complex of cyclen (1,4,7,10-tetraazacyclododecane) for catalytic group, and two imaging agents for binding group. This synthetic method was identified by H-NMR, C-NMR for intermediates and MS for the last products. The yields by this method surpassed solid phase synthesis and took much lower labor, expense, and time. The products which were synthesized by solution phase synthetic method showed good catalytic activities.

Keywords:Solution phase synthesis;Amyloid-cleaving catalysts;Triazine

[References]

Thangadurai TD, Ihm SK, J. Ind. Eng. Chem., 9(5), 569 (2003)
Chin. J. Acc. Chem. Res., 24, 145 (1991)
Chae PS, Kim MS, Jeung CS, Du Lee S, Park H, Lee S, Suh J, J. Am. Chem. Soc., 127(8), 2396 (2005)
Kim M, Jeon JW, Suh J, J. Biol. Inorg. Chem., 10, 364 (2005)
Yoo SH, Lee BJ, Kim H, Suh J, J. Am. Chem. Soc., 127(26), 9593 (2005)
Mathis CA, Wang Y, Holt DP, Huang GF, Debnath ML, Klunk WE, J. Med. Chem., 46, 2740 (2003)
Yukitsuka K, Minimally Invasive Therap., 14, 209 (2006)
Suh J, Yoo SH, Kim MG, Jeong K, Ahn JY, Kim MS, Chae PS, Lee TY, Lee J, Lee J, Jang YA, Ko EH, Angew. Chem. Int. Ed., 46, 7064 (2007)
Suh J, Chei WS, Lee T, Kim MG, Yoo SH, Jeong K, Ahn JY, J. Biol. Inorg. Chem., 13, 693 (2008)
Suh J, Lee J, Yoo SH, Jeong K, Lee TY, Ahn JY, Bull. Korean Chem. Soc., 29, 884 (2008)
Khersonsky SM, Chang YT, J. Comb. Chem., 6, 474 (2004)
Steffensen MB, Simanek EE, Org. Lett., 5, 2359 (2003)
Lowik DWPM, Lowe CR, Eur. J. Org. Chem., 2825 (2001)
Wang MX, Yang HB, J. Am. Chem. Soc., 126(47), 15412 (2004)
Scharn D, Wenschuh H, Reineke U, Schneider-Mergener J, Germeroth L, J. Comb. Chem., 2, 361 (2000)
Bork JT, Lee JW, Chang Y, QSAR Comb. Sci., 23 (2004)
Castillo-Blum SE, Sosa-Torres ME, Polyhedron, 14, 23 (1995)

[Referenced By]

[1] Thangadurai TD, Ihm SK, J. Ind. Eng. Chem., 9(5), 569 (2003)

[2] Chin. J. Acc. Chem. Res., 24, 145 (1991)

[3] Chae PS, Kim MS, Jeung CS, Du Lee S, Park H, Lee S, Suh J, J. Am. Chem. Soc., 127(8), 2396 (2005)

[4] Kim M, Jeon JW, Suh J, J. Biol. Inorg. Chem., 10, 364 (2005)

[5] Yoo SH, Lee BJ, Kim H, Suh J, J. Am. Chem. Soc., 127(26), 9593 (2005)

[6] Mathis CA, Wang Y, Holt DP, Huang GF, Debnath ML, Klunk WE, J. Med. Chem., 46, 2740 (2003)

[7] Yukitsuka K, Minimally Invasive Therap., 14, 209 (2006)

[8] Suh J, Yoo SH, Kim MG, Jeong K, Ahn JY, Kim MS, Chae PS, Lee TY, Lee J, Lee J, Jang YA, Ko EH, Angew. Chem. Int. Ed., 46, 7064 (2007)

[9] Suh J, Chei WS, Lee T, Kim MG, Yoo SH, Jeong K, Ahn JY, J. Biol. Inorg. Chem., 13, 693 (2008)

[10] Suh J, Lee J, Yoo SH, Jeong K, Lee TY, Ahn JY, Bull. Korean Chem. Soc., 29, 884 (2008)

[11] Khersonsky SM, Chang YT, J. Comb. Chem., 6, 474 (2004)

[12] Steffensen MB, Simanek EE, Org. Lett., 5, 2359 (2003)

[13] Lowik DWPM, Lowe CR, Eur. J. Org. Chem., 2825 (2001)

[14] Wang MX, Yang HB, J. Am. Chem. Soc., 126(47), 15412 (2004)

[15] Scharn D, Wenschuh H, Reineke U, Schneider-Mergener J, Germeroth L, J. Comb. Chem., 2, 361 (2000)

[16] Bork JT, Lee JW, Chang Y, QSAR Comb. Sci., 23 (2004)

[17] Castillo-Blum SE, Sosa-Torres ME, Polyhedron, 14, 23 (1995)