Department of Chemistry, University of Southampton, Southampton SO17 1BJ, United Kingdom
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http://www.avidplc.com, Avid PLC, East Sussex, TN22 3QY, UKMarsh, I.R., Bradley, M., (1997) Tetrahedron, 53, pp. 17317-17334
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Cleavage conditions were as follows: compounds bearing the Arg(NO2) moiety were cleaved with 90% TFA in DCM for 1.5 h
Fairlamb, A. H., Cerami, A., (1992) Annu. Rev. Microbiol., 46, pp. 695-72
Werbovetz, K. A., (2000) Curr. Med. Chem., 7, pp. 835-860. , For a review, see:
Smith, H. K., Bradley, M., (1999) J. Comb. Chem., 1, pp. 326-332
Houghton, R. A., (1985) Proc. Natl. Acad. Sci. USA, 82, pp. 5131-5135
Nicolaou, K. C., Xiao, X. Y., Parandoosh, Z., Senyei, A., Nova, M. P., (1995) Angew. Chem., Int. Ed. Engl., 34, pp. 2289-2291
Moran, E. J., Sarshar, S., Cargill, J. F., Shahbaz, M. M., Lio, A., Mjalli, A. M. M., Armstrong, R. W., (1995) J. Am. Chem. Soc., 117, pp. 10787-10788
http: //www. avidplc. com, Avid PLC, East Sussex, TN22 3QY, UKMarsh, I. R., Bradley, M., (1997) Tetrahedron, 53, pp. 17317-17334
K nig, W., Geiger, R., (1970) Chem. Ber., 103, pp. 788-798. , Reactions were monitored using a qualitative ninhydrin test on a small quantity of resin
Sarin, V. K., Kent, S. B. H., Tam, J. P., Merrifield, R. B., (1981) Anal. Biochem., 117, pp. 147-157
Solid-phase synthesis of a focused library of trypanothione reductase inhibitors
A focused library of inhibitors of the enzyme trypanothione reductase was prepared using solid-phase synthesis. The inhibitors were based on a previously identified, non-competitive, lead compound comprising of two Pmc (2,2,5,7,8-pentamethylchroman-6-sulfonyl) side-chain protected, N-capped arginine residues linked by a spermidine bridge. In total six protecting groups and four capping groups were used to generate a 24-membered library. All compounds bearing the 5-methoxyindole-3-acetic acid capping group were found to have good activity. The most potent inhibitor was observed to contain the Mtr (4-methoxy-2,3,6-trimethylbenzenesulphonyl) protecting group on the arginine residue, terminated with tryptophan as the capping group. (C) 2003 Elsevier Science Ltd. All rights reserved.
Solid-phase synthesis of a focused library of trypanothione reductase inhibitors
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