Solid-phase total synthesis of (-)-Phenylhistine and (-)-Aurantiamine. Synthesis of a diverse dehydro-2,5-diketopiperazine library. Part II

Molecular Diversity

Volumn 9, Issue 1-3, 2005, Pages 111-121

  Couladouros, Elias A ^a,b   Magos, Alexandros D ^a,b  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^b NCSR DEMOKRITOS   (Greece)

Author keywords

2,5 diketopiperazines; Amino acids; Combinatorial chemistry; Horner Emmons reaction; Library; Natural products; Solid phase synthesis

Indexed keywords

AMINE; AMINO ACID; AURANTIAMINE; BENZENE DERIVATIVE; DEHYDRO 2,5 DIKETOPIPERAZINE; GLYCINE DERIVATIVE; GLYCINE PHOSPHONATE; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; PHENYLHISTINE; PHOSPHONIC ACID DERIVATIVE; PIPERAZINE DERIVATIVE; PYRIDINE DERIVATIVE; THIAZOLE; UNCLASSIFIED DRUG;

ARTICLE; COMBINATORIAL CHEMISTRY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; SOLID;

INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PIPERAZINES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 15444367904     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-005-1295-9     Document Type: Article

References (32)

1. Couladouros, E.A. and Strongilos, A.T., Generation of libraries of pharmacophoric structures with increased complexity and diversity by employing polymorphic scaffolds, Angew. Chem. Int. Ed., 41 (2002) 3677-3680.
2. Schmidt, U., Lieberknecht, A. and Wild J., Amino acids and peptides; XLIII. Dehydroamino acids; XVIII. Synthesis of dehydroamino acids and amino acids from N-Acyl-2-(dialkyloxyphosphinyl)-glycin esters; II, Synthesis, 4 (1984) 53-60.
3. Schmidt, U., Leitenberger, V., Griesser, H., Schmidt, J. and Meyer, R., Total synthesis of the biphenomycins; V. synthesis of biphenomycin A, Synthesis, 12 (1992) 1248-1254.
4. Schmidt, U., Lieberknecht, A., Griesser, H., Utz, R., Beuttler, T. and Bartkowiak, F., Amino acids and peptides; 55. Synthesis of biologically active cyclopeptides; 7. Total synthesis of chlamydocin, Synthesis, 6 (1986) 361-366.
5. Brown, J.A., Synthesis of N-aryl-indole-2-carboxylates via an intramolecular palladium-catalysed annulation of didehydrophenylalanine derivatives, Tetrahedron Lett., 41 (2000) 1623-1626.
6. Lotz, B.T. and Miller, M.J., Diastereoselective synthesis of the carbacephem framework, J. Org. Chem., 58 (1993) 618-625.
7. Stocksdale, M.G., Ramurthy, S. and Miller, M.J., Asymmetric total synthesis of an important 3-(hydroxymethyl)-carbacephalosporin, J. Org. Chem., 63 (1998) 1221-1225.
8. Rousseau, J.-F. and Dodd, R.H., Synthesis of 3-deaza-β- hydroxyhistidine derivatives and their use for the preparation of substituted pyrrolo[2,3-c]pyridine-5-carboxylates via the Pictet-Spengler reaction, J. Org. Chem., 63 (1998) 2731-2737.
9. Jørgensen, K.B. and Gautun, O.R., Efficient stereoselective preparation of protected isodityrosines, Tetrahedron, 55 (1999) 10527-10536.
10. Jiménez, J.M., Rifé, J. and Ortuño R.M., Enantioselective total synthesis of cyclopropane amino acids: Natural products and protein methanologs, Tetrahedron: Asymmetry, 7 (1996) 537-558.
11. Shieh, W.-C., Xue, S., Reel, N., Wu, R., Fitt, J. and Repič, O., An enantioselective synthesis of (R)-4-piperidinylglycine, Tetrahedron: Asymmetry, 12 (2001) 2421-2425.
12. B site of (+)- and (-)-3-oxetanylglycine, novel non-proteinogenic amino acids, Il Farmaco, 56 (2001) 609-613.
13. y Antigens, J. Am. Chem. Soc., 123 (2001) 1890-1897.
14. kTrisaccharide, J. Org. Chem., 64 (1999) 9153-9163.
15. Nicolaou, K.C., Murphy, F., Barluenga, S., Ohshima, T., Wei, H., Xu, J., Gray, D.L.F. and Baudoin, O., Total synthesis of the novel immunosuppressant sanglifehrin A, J. Am. Chem. Soc., 122 (2000) 3830-3838.
16. Bagley, M.C., Hind, S.L. and Moody, C.J., Studies towards the synthesis of diazonamide A. Synthesis of the indole bis-oxazole fragment, Tetrahedron Lett., 41 (2000) 6897-6900.
17. Sowinski, J.A. and Toogood, P.L., Synthetic studies towards keramamide F, Tetrahedron Lett., 36 (1995) 67-70.
18. Adamczyk, M., Rao Akireddy, S. and Reddy, R.E., Asymmetric synthesis of (S)-(-)-acromelobinic acid, Tetrahedron: Asymmetry, 12 (2001) 2385-2387.
19. Coleman, R.S., Li, J. and Navarro, A., Total synthesis of azinomycin A, Angew. Chem. Int. Ed., 40 (2001) 1736-1739.
20. Schiavi, B.M., Richard, D.J. and Joullié, M.M., Total synthesis of isoroquefortine C, J. Org. Chem., 67 (2002) 620-624.
21. Szardenings, A.K., Antonenko, V., Campbell, D.A., DeFrancisco, N., Ida, S., Shi, L., Sharkov, N., Tien, D., Wang, Y. and Navre, M., Identification of highly selective inhibitors of collagenase-1 from combinatorial libraries of diketopiperazines, J. Med. Chem., 42 (1999) 1348-1357.
22. Szardenings, A.K., Harris, D., Lam, S., Shi, L., Tien, D., Wang, Y., Patel, D.V., Navre, M. and Campbell, D.A., Rational design and combinatorial evaluation of enzyme inhibitor scaffolds: Identification of novel inhibitors of matrix metalloproteinases, J. Med. Chem., 41 (1998) 2194-2200.
23. Bianco, A., Sonksen, C.P., Roepstorff, P. and Briand, J.-P., Solid-phase synthesis and structural characterization of highly substituted hydroxyproline-based2,5-diketopiperazines, J. Org. Chem., 65 (2000) 2179-2187.
24. Kanoh, K., Kohno, S., Asari, T., Harada, T., Katada, J., Muramatsu, M., Kawashima, H., Sekiya, H. and Uno, I., (-)-Phenylahistin: A new mammalian cell cycle inhibitor produced by Aspergillus Ustus, Bioorg. Med. Chem. Lett., 7 (1997) 2847-2852.
25. Larsen, T.O., Frisvad, J.C. and Jensen, S.R., Aurantiamine, a dike-topiperazine from two varieties of penicillium aurantiogriseum, Phytochemistry, 31 (1992) 1613-1615.
26. Loughlin, W.A., Marshall, R.L., Carreiro, A. and Elson, K.E., Solution-phase combinatorial synthesis and evaluation of piperazine-2,5-dione derivatives, Bioorg. Med. Chem. Lett., 10 (2000) 91-94.
27. Li, W.-R. and Yang, J.H., Solid-phase synthesis of unsaturated 3-substituted piperazine-2,5-diones, J. Comb. Chem., 4 (2002) 106-108.
28. Couladouros, E.A. and Magos, A.D., Total asymmetric synthesis of (-)-Phenylhistine, (-)-Aurantiamine and related compounds. Part I.
29. Couladouros, E.A., Magos, A.D. and Strongilos, A.T., Methods of preparation of dehydro-diketopiperazines, PCT/GR03/00028, (2003).
30. Nicolaou, K.C., Pastor, J., Winssinger, N. and Murphy, F., Solid phase synthesis of macrocycles by an intramolecular ketophosphonate reaction. Synthesis of a (dl)-muscone library, J. Am. Chem. Soc, 120 (1998) 5132-5133.
31. Kaiser, E., Colescott, R.L., Bossinger, C.D. and Cook, P.I., Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides, Anal. Biochem., 34 (1970) 595-598.
32. Sarin, V.K., Kent, S.B.H., Tam, J.P. and Merrifield, R.B., Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction, Anal. Biochem., 117 (1981) 147-157.