cis- and trans-3-(3-indolyl)proline derivatives as conformationally restricted analogues of tryptophan

Synlett

Volumn , Issue 6, 1999, Pages 786-788

  Damour, D ^a   Pulicani, J P ^a   Vuilhorgne, M ^a   Mignani, S ^a  

^a SANOFI   (France)

Author keywords

3 (3 indolyl)prolines; Azomethine ylide; Constrained amino acids; Cycloaddition; Tryptophan analogue

Indexed keywords

INDOLE DERIVATIVE; MALONIC ACID DERIVATIVE; N ETHOXYCARBONYL N METHOXYMETHYLAMINOMALONIC ACID; PROLINE DERIVATIVE; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DERIVATIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033040773     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2708     Document Type: Article

References (42)

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11. b) For conformationally restricted proline analogues of phenylalanine, see: Belokon, Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Belikov, V. M.; J. Chem. Soc. Perkin Trans 1, 1988, 2075; Sarges, R. ; Tretter, J. R. J. Org. Chem. 1974, 39, 12, 1710 ; Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W.; J. Org. Chem., 1990, 55, 270; Holladay, M. W. ; Lin, C. W.; May, C. S.; Garvey, D. S.; Witte, D. G.; Miller,T. R.; Wolfram, C. A.; Nadzan, A. M.; J. Med. Chem., 1991, 34, 457.
12. b) For conformationally restricted proline analogues of phenylalanine, see: Belokon, Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Belikov, V. M.; J. Chem. Soc. Perkin Trans 1, 1988, 2075; Sarges, R. ; Tretter, J. R. J. Org. Chem. 1974, 39, 12, 1710 ; Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W.; J. Org. Chem., 1990, 55, 270; Holladay, M. W. ; Lin, C. W.; May, C. S.; Garvey, D. S.; Witte, D. G.; Miller,T. R.; Wolfram, C. A.; Nadzan, A. M.; J. Med. Chem., 1991, 34, 457.
13. b) For conformationally restricted proline analogues of phenylalanine, see: Belokon, Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Belikov, V. M.; J. Chem. Soc. Perkin Trans 1, 1988, 2075; Sarges, R. ; Tretter, J. R. J. Org. Chem. 1974, 39, 12, 1710 ; Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W.; J. Org. Chem., 1990, 55, 270; Holladay, M. W. ; Lin, C. W.; May, C. S.; Garvey, D. S.; Witte, D. G.; Miller,T. R.; Wolfram, C. A.; Nadzan, A. M.; J. Med. Chem., 1991, 34, 457.
14. b) For conformationally restricted proline analogues of phenylalanine, see: Belokon, Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Belikov, V. M.; J. Chem. Soc. Perkin Trans 1, 1988, 2075; Sarges, R. ; Tretter, J. R. J. Org. Chem. 1974, 39, 12, 1710 ; Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W.; J. Org. Chem., 1990, 55, 270; Holladay, M. W. ; Lin, C. W.; May, C. S.; Garvey, D. S.; Witte, D. G.; Miller,T. R.; Wolfram, C. A.; Nadzan, A. M.; J. Med. Chem., 1991, 34, 457.
15. c) For conformationally restricted proline analogues of tyrosine, see : Waid, P. P.; Flyn, G. A.; Huber, E. W.; Sabol, J. S.; Tetrahedron Lett., 1996, 37, 24, 4091.
16. d) For conformationally restricted proline analogues of aspartic acid and glutamic acid, see: Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W.; J. Org. Chem., 1990, 55, 270 ; Moss, W. O.; Bradbury, R. H. ; Hales, N. J.; Gallagher, T. ; Tetrahedron Lett., 1990, 31, 39, 5653 ; Hashimoto, K. ; Yamamoto, O. ; Horikawa, M. ; Ohfune, Y. ; Shirahama, H. ; Bioorg. & Med. Chem. Lett., 1994, 4, 15, 1851; Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P.; Tetrahedron Lett., 1994, 35, 2, 241 ; Carpes, M. J. S.; Miranda, P. C.; Correia, C. R.; Tetrahedron Lett., 1997, 38, 11, 1869.
17. d) For conformationally restricted proline analogues of aspartic acid and glutamic acid, see: Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W.; J. Org. Chem., 1990, 55, 270 ; Moss, W. O.; Bradbury, R. H. ; Hales, N. J.; Gallagher, T. ; Tetrahedron Lett., 1990, 31, 39, 5653 ; Hashimoto, K. ; Yamamoto, O. ; Horikawa, M. ; Ohfune, Y. ; Shirahama, H. ; Bioorg. & Med. Chem. Lett., 1994, 4, 15, 1851; Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P.; Tetrahedron Lett., 1994, 35, 2, 241 ; Carpes, M. J. S.; Miranda, P. C.; Correia, C. R.; Tetrahedron Lett., 1997, 38, 11, 1869.
18. d) For conformationally restricted proline analogues of aspartic acid and glutamic acid, see: Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W.; J. Org. Chem., 1990, 55, 270 ; Moss, W. O.; Bradbury, R. H. ; Hales, N. J.; Gallagher, T. ; Tetrahedron Lett., 1990, 31, 39, 5653 ; Hashimoto, K. ; Yamamoto, O. ; Horikawa, M. ; Ohfune, Y. ; Shirahama, H. ; Bioorg. & Med. Chem. Lett., 1994, 4, 15, 1851; Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P.; Tetrahedron Lett., 1994, 35, 2, 241 ; Carpes, M. J. S.; Miranda, P. C.; Correia, C. R.; Tetrahedron Lett., 1997, 38, 11, 1869.
19. d) For conformationally restricted proline analogues of aspartic acid and glutamic acid, see: Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W.; J. Org. Chem., 1990, 55, 270 ; Moss, W. O.; Bradbury, R. H. ; Hales, N. J.; Gallagher, T. ; Tetrahedron Lett., 1990, 31, 39, 5653 ; Hashimoto, K. ; Yamamoto, O. ; Horikawa, M. ; Ohfune, Y. ; Shirahama, H. ; Bioorg. & Med. Chem. Lett., 1994, 4, 15, 1851; Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P.; Tetrahedron Lett., 1994, 35, 2, 241 ; Carpes, M. J. S.; Miranda, P. C.; Correia, C. R.; Tetrahedron Lett., 1997, 38, 11, 1869.
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22. For a recent review on conformationally constrained analogues of Phe, Tyr, Trp and His, see; Gibson, S. E. ; Guillo, N.; Tozer, M. J. Tetrahedron, 1999, 55, 585 and references cited therein a) Horwell, D. C. ; Nichols, P. D. ; Roberts, E, ; Tetrahedron Lett., 1994, 35, 939 ; Horwell, D. C. ; Nichols, P. D. ; Ratcliffe, G. S. ; Roberts, E., J. Org. Chem., 1994, 59, 4418 ; Irie, K. ; Iguchi, M., Oda, T. ;Suzuki, Y .; Okuno, S. ; Ohigashi, H. ; Koshimizu, K. ; Tetrahedron, 1995, 51, 6255 ; Horwell, D.C, ; McKiernan, M. J. ; Naylor, D. ; Osborne, S. A. ; Lett. Pept. Sci., 1998, 5, 143
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24. For a recent review on conformationally constrained analogues of Phe, Tyr, Trp and His, see; Gibson, S. E. ; Guillo, N.; Tozer, M. J. Tetrahedron, 1999, 55, 585 and references cited therein a) Horwell, D. C. ; Nichols, P. D. ; Roberts, E, ; Tetrahedron Lett., 1994, 35, 939 ; Horwell, D. C. ; Nichols, P. D. ; Ratcliffe, G. S. ; Roberts, E., J. Org. Chem., 1994, 59, 4418 ; Irie, K. ; Iguchi, M., Oda, T. ;Suzuki, Y .; Okuno, S. ; Ohigashi, H. ; Koshimizu, K. ; Tetrahedron, 1995, 51, 6255 ; Horwell, D.C, ; McKiernan, M. J. ; Naylor, D. ; Osborne, S. A. ; Lett. Pept. Sci., 1998, 5, 143
25. For a recent review on conformationally constrained analogues of Phe, Tyr, Trp and His, see; Gibson, S. E. ; Guillo, N.; Tozer, M. J. Tetrahedron, 1999, 55, 585 and references cited therein a) Horwell, D. C. ; Nichols, P. D. ; Roberts, E, ; Tetrahedron Lett., 1994, 35, 939 ; Horwell, D. C. ; Nichols, P. D. ; Ratcliffe, G. S. ; Roberts, E., J. Org. Chem., 1994, 59, 4418 ; Irie, K. ; Iguchi, M., Oda, T. ;Suzuki, Y .; Okuno, S. ; Ohigashi, H. ; Koshimizu, K. ; Tetrahedron, 1995, 51, 6255 ; Horwell, D.C, ; McKiernan, M. J. ; Naylor, D. ; Osborne, S. A. ; Lett. Pept. Sci., 1998, 5, 143
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41. 4: C, 65.43; H,6.71; N, 8.48; O, 19.37. Found : C, 65.1; H, 6.7; N, 8.2; O, 19.3. NMR assignments were secured by 2D COSY experiments while the relative stereochemistry was confirmed by nOe experiments performed on compounds 4 trans and 4 cis: larger effects were observed between H2, H3 and H2' for the trans arrangement compared to the cis derivative.
42. Silica gel 60 (0.063-0.2 mm), Merck.