From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics

Tetrahedron Letters

Volumn 47, Issue 38, 2006, Pages 6711-6714

  González, Juan Francisco ^a   de la Cuesta, Elena ^a   Avendaño, Carmen ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3(4) AMINOPHENYL ALPHA KETOPROPIONIC ACID; 6 AMINOINDOLE 2 CARBOXYLIC ACID; AMINO ACID DERIVATIVE; DIPEPTIDE DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; NITRO DERIVATIVE; TRIPEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALCOHOLYSIS; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CYCLIZATION; DRUG SYNTHESIS; MICROWAVE RADIATION; REDUCTION KINETICS; THERMODYNAMICS;

EID: 33747168191     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.095     Document Type: Article

References (29)

1. Hashimoto Y., Aoyagi H., Waki M., Kato T., and Izumiya N. Int. J. Protein Res. 21 (1983) 11-15
2. Oba M., Terauchi T., Owari Y., Imai Y., Motoyama I., and Nishiyama K. J. Chem. Soc., Perkin Trans. 1 (1998) 1275-1281
3. Kukula P., and Prins R. Diastereoselective hydrogenation in the preparation of Fine Chemicals. Topics in Catalysis Vol. 25 (2003), Springer-Science+Business media B. 29-42
4. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893-930
5. For summary of the applications of indoles, see:. Gribble G.W. Five-membered rings with one heteroatom and fused carbocyclic derivatives. In: Bird C.W., Katrizky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry. 2nd ed. Vol. 2 (1995), Pergamon Press, Oxford 207-257
6. Williams T.M., Ciccarone T.M., MacTough S.C., MacTough S.C., Rooney C.S., Balani S.K., Condra J.H., Emini E.A., Goldman M.E., Greenlee W.J., Kauffman L.R., O'Brien J.A., Sardana V.V., Schleif W.A., Theoharides A.D., and Anderson P.S. J. Med. Chem. 36 (1993) 1291-1294
7. Romero D.L., Morge R.A., Biles C., Berrios-Peña N., May P.D., Palmer J.R., Johnson P.D., Smith H.V., Busso M., Tan Ch.-K., Voorman R.L., Reusser F., Althaus I.W., Downey K.M., So A.G., Resnick L., Tarpley W.G., and Aristoff P.A. J. Med. Chem. 37 (1994) 999-1014
8. Ichimura M., Ogawa T., Takahashi K., Kobayashi E., Kawamoto I., Yasuzawa T., Takahashi I., and Nakano H. J. Antibiot. 43 (1990) 1037-1038
9. Kobayashi E., Okamoto A., Asada N., Okabe M., Nagamura S., Asai A., Saito H., Gosni K., and Hirata T. Cancer Res. 54 (1994) 2404-2410
10. Gribble G.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1045-1075
11. Moody C.J., and Rahimtoola K.F. J. Chem. Soc., Perkin 1 (1990) 673-679
12. Tsuji Y., Kotachi S., Huhm K.-T., and Watanabe Y. J. Org. Chem. 55 (1990) 580-584
13. Schreiber S.L. Science 251 (1991) 283-287
14. Kende A.S., Liu K., Kaldor I., Dorey G., and Koch K. J. Am. Chem. Soc. 117 (1995) 8258-8270
15. Han W., Hu Z., Jiang X., and Decicco C.P. Bioorg. Med. Chem. 10 (2000) 711-713
16. Sun D.X., Liu L., Heinz B., Kolykhalov A., Lamar J., Johnson R.B., Wang Q.M., Yip Y., and Chen S. Bioorg. Med. Chem. 14 (2004) 4333-4338
17. Chen K.X., Njoroge F.G., Arasappan A., Venkatraman S., Vibulbhan B., Yang W., Parekh T.N., Pichardo J., Prongay A., Cheng K., Butkiewicz N., Yao N., Madison V., and Girijavallabhan V. J. Med. Chem. 49 (2006) 995-1005
18. Bach R.D., Mintcheva I., Kronenberg W.J., and Schlegel H.B. J. Org. Chem. 58 (1993) 6135-6138
19. Kahn K., and Bruice T.C. Bioorg. Med. Chem. 8 (2000) 1881-1891
20. Yang Z., Zhang Z., Meanwell N.A., Kadow J.F., and Wang T. Org. Lett. 4 (2002) 1103-1105
21. Nakamura M., Inoue J., and Yamada T. Bioorg. Med. Chem. Lett. 10 (2000) 2807-2910
22. González J.F., Salazar L., de la Cuesta E., and Avendaño C. Tetrahedron 61 (2005) 7447-7455
23. Li W., and Peng S. Tetrahedron Lett. 39 (1998) 7373-7376
24. González J.F., de la Cuesta E., and Avendaño C. Synth. Commun. 34 (2004) 1589-1597
25. 5: C, 53.98; H, 3.83; N, 14.53. Found: C, 53.63; H, 3.87; N, 14.18.
26. 6: C, 60.67; H, 4.53; N, 7.85. Found: 60.82; H, 4.70; N, 7.65.
27. 6: C, 51.43; H, 4.32; N, 10.00. Found: C, 51.29; H, 4.15; N, 9.82.
28. 3: C, 60.55; H, 4.62; N, 12.84. Found: C, 60.34; H, 4.23; N, 12.60.
29. 7: C, 62.76; H, 6.28; N, 8.45. Found: C, 62.48; H, 6.15; N, 8.32.