Synthesis of 4-des-hydroxyl clorobiocin analogues as possible bacterial DNA gyrase B and human Hsp90 inhibitors

doi:10.5246/jcps.2011.03.027

Abstract

Abstract:

Aminocoumarin natural products are known as inhibitors of both bacterial DNA gyrase B and human Hsp90. Due to the lack of efficient synthetic approach, structure activity relationship (SAR) understandings of these molecules are still limited. Synthesis of a set of novel 4-des-hydroxyl clorobiocin analogues, including the de novo construction of properly functionalized L-noviose building blocks and the subsequent assembly of the target molecules, is described in full detail. Expanded application of this synthetic protocol is expected to help gaining more information about the SAR of aminocoumarins.

Key words: Clorobiocin, 4-Des-hydroxyl analogue, Synthesis

CLC Number:

R916

Supporting:

Yi-Qiu He, Yong-Qiang Li, Liang Ma, Xiao-Ming Yu^* . Synthesis of 4-des-hydroxyl clorobiocin analogues as possible bacterial DNA gyrase B and human Hsp90 inhibitors [J]. , DOI: 10.5246/jcps.2011.03.027.

References

[1] Maxwell, A. Trends Microbiol. 1997, 5, 102-109.
[2] Hoeksema, H.; Johnson, J.L.; Hinman, J.W. J. Am. Chem. Soc. 1955, 77, 6710-6711.
[3] Smith, C.G.; Dietz, A.; Sokolski, W.T.; Savage, G.M. Antibiot. Chemother. 1956, 6, 135-142.
[4] Maxwell, A. Mol. Microbiol. 1993, 9, 681-686.
[5] Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
[6] Lewis, R.J.; Tsai, F.T.F.; Wigley, D.B. Bioessays. 1996, 18, 661-671.
[7] Maxwell, A.; Lawson, D.M. Curr. Top. Med. Chem. 2003, 3, 283-303.
[8] Marcu, M.G.; Schulte, T.W.; Neckers, L. J. Natl. Cancer Inst. 2000, 92, 242-248.
[9] Donnelly, A.; Blagg, B.S.J. Curr. Med. Chem. 2008, 15, 2702-2717.
[10] Oblak, M.; Kotnik, M.; Solmajer, T. Curr. Med. Chem. 2007, 14, 2033-2047.
[11] Heide, L. Nat. Prod. Rep. 2009, 26, 1241-1250.
[12] Li, S.M.; Heide, L. Curr. Med. Chem. 2005, 12, 419-427.
[13] Bisacchi, G.S.; Dumas, J. Annu. Rep. Med. Chem. 2009, 44, 379-396.
[14] Yu, X.M.; Shen, G.; Neckers, L.; Blake, H.; Holzbeierlein, J.; Cronk, B.; Blagg, B.S.J. J. Am. Chem. Soc. 2005, 127, 12778-12779.
[15] Burlison, J.A.; Neckers, L.; Smith, A.B.; Maxwell, A.; Blagg, B.S. J. J. Am. Chem. Soc. 2006, 128, 15529-15536.
[16] Allan, R.K.; Mok, D.; Ward, B.K.; Ratajczak, T. J. Biol. Chem. 2006, 281, 7161-7171.
[17] He, Y.; Xue, J.; Zhou, Y.; Yang, J.; Yu, X. Tetrahedron Lett. 2009, 50, 2317-2319.
[18] Hanessian, S.; Auzzas, L. Org. Lett. 2008, 10, 261-264.
[19] Reddy, D.S.; Srinivas, G.; Rajesh, B.M.; Kannan, M.; Rajale, T.V.; Iqbal, J. Tetrahedron Lett. 2006, 47, 6373-6375.
[20] Laurin, P.; Ferroud, D.; Schio, L.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2875-2880.
[21] Olson, S.H.; Slossberg, L.H. Tetrahedron Lett. 2003, 44, 61-63.
[22] Curran, T.P.; Keaney, M.T. J. Org. Chem. 1996, 61, 9068-9069.
[23] Perkin, W.H. J. Chem. Soc. 1877, 32, 388-427.