Cyclopropane-derived peptidomimetics. Design, synthesis, and evaluation of novel enkephalin analogues

Journal of Organic Chemistry

Volumn 65, Issue 5, 2000, Pages 1305-1318

  Martin, Stephen F ^a   Dwyer, Michael P ^a   Hartmann, Benoît ^a   Knight, Kyle S ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYL COMPOUND; CYCLOPROPANE DERIVATIVE; DIPEPTIDE DERIVATIVE; ENKEPHALIN DERIVATIVE; GLYCYLGLYCINE; LACTONE DERIVATIVE; LEUCINE ENKEPHALIN DERIVATIVE; MU OPIATE RECEPTOR; PHENYLALANINE DERIVATIVE; RHODIUM COMPLEX;

AMIDATION; ARTICLE; CATALYSIS; CHIRALITY; CYCLIZATION; DRUG CONFORMATION; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SCREENING; ENANTIOMER; MOLECULAR MIMICRY; MOLECULAR MODEL; PEPTIDE SYNTHESIS; RECEPTOR AFFINITY; STEREOCHEMISTRY;

ANIMALS; BINDING, COMPETITIVE; BRAIN; CELL MEMBRANE; CYCLIZATION; CYCLOPROPANES; DRUG DESIGN; ENKEPHALIN, LEUCINE; GUINEA PIGS; ILEUM; INHIBITORY CONCENTRATION 50; MALE; MICE; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; PROTEIN BINDING; RECEPTORS, OPIOID; VAS DEFERENS;

EID: 0034629434     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991288h     Document Type: Article

References (82)

1. For leading reviews, see: (a) Spatola, A. F. In Chemistry and Biochemistry ofAmino Acids, Peptides, and Proteins; Weinstein, B., Ed; Marcel Dekker: New York 1983; Vol. 7, pp 267-357.
2. (b) Hruby, B. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990,268, 249-262.
3. Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M.; Fry, D. C.; Graves,' B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Ruisiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993,36,3039-3049.
4. Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Eng. 1993,32,1244-1267.
5. (e) Gante, J. Angew. Chem., Int. Ed. Eng. 1994, 33, 1699-1720.
6. (0 Hanessian, S.; McNaughtonSmith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997,3, 1278912854.
7. (g) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
8. 2. For example, see: (a) Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 65686570.
9. (b) Smith, A. B., Ill; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947-9962.
10. Chen, L.; Trilles, R. V. Tetrahedron Lett. 1995,36, 8715-8718.
11. Boumendjel, A.; Roberts, J. C.; Hu, E.; Pallai, P. V.; Rebek, Jr., J. J. Org. Chem. 1996,61,44344438.
12. (e) Janetka, J. W.; Raman, P.; Satyshur, K.; Flentke, G. R.; Rich, D. H. J. Am. Chem. Soc. 1997,119, 441-442.
13. For leading reviews, see: (a) Gillespie, P.; Cicariello, J.; Olson, G. L. Biopolymer 1997,43,191-217.
14. (b) Hruby, V. J.; Li, G.; HaskellLuevano, C.; Shenderovich, M. Biopolymer 1997, 43, 219-266.
15. Martin, S. F.; Austin, R. E.; Oalmann, C. J. Tetrahedron Lett. 1990, 31, 4731-4734.
16. (a) Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Baker, W. R.; Condon, S. L.; DeLara, E.; Rosenberg, S. H.; Spina, K. P.; Stein, H. H.; Cohen, J.; Kleinert, H. D. J. Med. Chem. 1992,35,1710-1721.
17. (b) Baker, W. R.; Jae, H.-S.; Martin, S. F.; Condon, S. L.; Stein, H. H.; Cohen, J.; Kleinert, H. D. BioMed. Chem. Lett. 1992, 2, 1405-1410.
18. (a) Martin, S. F.; Dorsey, G. O.; Gane, T. H.; Hillier, M.; Kessler, H.; Baur, M.; Mathä, B.; Erickson, J. W.; Bhat, N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581-1597.
19. (b) Hillier, M. C.; Martin, S. F. In Methods in Molecular Medicine: Vol. 30, Peptidomîmetics Protocols, Kazmierski, W. M., Walker, J. M., Eds.; Humana Press: Totowa, N. J., 1999; pp 397-406.
20. Martin, S. F.; Oalmann, C. J.; Liras, S. Tetrahedron 1993, 49, 3521-3532
21. Martin, S. F.; Horn, R. K. Tetrahedron Lett. 1999, 40, 28872890.
22. For a review, see: Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359-1472.
23. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467-3478.
24. (a) Kennedy, A. L. Masters Thesis, The University of Texas at Austin, 1996.
25. (b) Frey, R. R. Masters Thesis, The University of Texas at Austin, 1998.
26. Gaul, C. Masters Thesis, The University of Texas at Austin, 1998.
27. Bovy, P. R.; Tjoeng, F. S.; Rico, J. G.; Rogers, T. E.; Lindmark, R. J.; Zablocki, J. A.; Garland, R. B.; McMackins, D. E.; Dayringer, H.; Toth, M. V.; Zupec, M. E.; Rao, S.; Panzer-Knodle, S. G.; Nicholson, N. S.; Salyers, A.; Taite, B. B.; Herin, M.; Miyano, M.; Feigen, L. P.; Adaras, S. P. Bioorg. Med. Chem. 1994, 2, 881-895.
28. For leading references to conformational calculations of the enkephalins, see: (a) Montcalm, T.; Cui, W.; Zhao, H.; Guarnieri, F.; Wilson, S. R. J. Mol. Struct. (THEOCHEM) 1994,308,37-51.
29. (b) Koca, J.; Carlsen, P. H. J. J. Mol. Struct. (THEOCHEM) 1995,337,17-24.
30. For reviews, see: (a) Schiller, P. W. In The Peptides: Analysis, Synthesis, Biology. Vol. 6. Opioid Peptides: Biology, Chemistry and Genetics; Udenfriend, S.; Meienhofer, J., Eds.; Academic Press: New York, 1984; pp 219-268.
31. (b) Hansen, P. E.; Morgan, B. A. In The Peptides: Analysis, Synthesis, Biology. Vol. 6. Opioid Peptides: Biology, Chemistry and Genetics; Udenfriend, S.; Meienhofer, J., Eds.; Academic Press: New York, 1984; pp 269-321.
32. ". (a) Hruby, V. J.; Pettit, B. M. In Computer Aided Drug Design; Perun, T., Probst, C., Eds.; Dekker: New York, 1989; pp 406460.
33. (b) Hruby, V. J.; Toth, G.; Gehrig, C. A.; Kao, L.-F.; Knapp, R.; Lui, G. K.; Yamamura, H. L; Kramer, T. H.; Davis, P.; Burks, T. F. J. Med. Chem. 1991,34,1823-1830.
34. Kazmierski, W. M.; Yamamura, H. I.; Hruby, V. J. J. Am. Chem. Soc. 1991, 113, 2275-2283.
35. Schüler, P. W.; Weltrowska, G.; Nguyen, T. M.-D.; Lemieux, C.; Chung, N. N.; Marsden, B. J.; Wilkes, B. C. J. Med. Chem. 1991, 34, 31253132.
36. (e) Schiller, P. W.; Weltrowska, G.; Nguyen, T. M.-D.; Wilkes, B. C.; Chung, N. N.; Lemieux, C. J. Med. Chem. 1993,36, 3182-3187.
37. (0 Lomize, A. L.; Flippen-Anderson, J. L.; George, C.; Mosberg, H. I. J. Am. Chem. Soc. 1994,116, 429-436.
38. (g) Mosberg, H. I.; Lomize, A. L.; Wang, C.; Kroona, H.; Heyl, D. L.; Sobczyk-Kojiro, K; Ma, W.; Mousigian, C.; Porreca, F. J. Med. Chem. 1994, 37, 4371-4383.
39. (h) Mosberg, H. L; Omnaas, J. R.; Lomize, A. L.; Heyl, D. L.; Nordan, L; Mousigian, C.; Davis, P.; Porreca, F. J. Med. Chem. 1994, 37, 43844391.
40. Flippen-Anderson, J. L.; Hruby, V. J.; Collins, N.; George, C.; Cudney, B. J. Am. Chem. Soc. 1994, 116, 7523-7531.
41. (j) Collins, N.; Flippen-Anderson, J. L.; Haaseth, R. C.; Deschamps, J. R.; George, C.; Köver, K.; Hruby, V. J. J. Am. Chem. Soc. 1996,118, 2143-2152.
42. (a) Currie, B. L.; Krstenansky, J. L.; Lin, Z.-L.; Ungwitayatorn, J.; Lee, Y.-H.; del Rosario-Chow, M.; Sheu, W.-S.; Johnson, M. E. Tetrahedron 1993, 49, 3489-3500.
43. (b) Su, T.; Nakanishi, H.; Xue, L.; Chen, B.; Tuladhar, S.; Johnson, M. E.; Kahn, M. BioMed. Chem. Lett. 1993, 3, 835-840.
44. Spatola, A. F.; Saneii, H.; Edwards, J. V.; Bettag, A. L.; Amver, M. K.; Rowell, P.; Browne, B.; Lahti, R.; von Voigtlander, P. Life Sei. 1986, 38, 1243-1249.
45. Roubini, E.; Laufer, R.; Gilon, C.; Selinger, Z.; Roques, B. P.; Chorev, M. J. Med. Chem. 1991, 34, 2430-2438.
46. (a) Shimohigashi, Y.; English, M. L.; Stammer, C. H.; Costa, T. Biochem. Biophys. Res. Commun. 1982,104, 583-590.
47. (b) Kimura, H.; Stammer, C. H.; Shimohigashi, Y.; Lin, C. R.; Stewart, J. Biochem. Biophys. Res. Commun. 1983, 115, 112-115.
48. Shimohigashi, Y.; Costa, T.; Nitz, T. J.; Chen, C. H.; Stammer, C. H. Biochem. Biophys. Res. Commun. 1984,121, 966-972.
49. (a) Doyle, M. P.; Pieters, R. J.; Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Müller, P. J. Am. Chem. Soc. 1991, 113, 1423-1424.
50. (b) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763-5775.
51. Martin, S. F.; Spalier, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494.
52. (a) Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977,4171-4174.
53. (b) Sibi, M. P. Org. Prep. Proc. Int. 1993 25,15-40.
54. For an independent report of a related process, see: Hanko, R.; Rabe, K; Dally, R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1690-1693.
55. Martin, S. F.; Dwyer, M. P.; Lynch, C. L. Tetrahedron Lett. 1998, 39, 1517-1520.
56. For example, see: (a) Schroff, C. C.; Stewart, W. S.; Uhm, S J.; \Vheeler, J. W. J. Org. Chem. 1971,36, 3356-3361.
57. (b) Cannon, J. G.; Garst, J. E. J. Org. Chem. 1975, 40, 182-184.
58. Paulini, K.; Reissig, H.-R. Liebigs Ann. Chem. 1991, 455-461.
59. Paulini, K.; Reissig, H.-U. Liebigs Ann. Chem. 1994, 549-554.
60. See also: (e) Von Der Saal, W.; Quast, H. J. Org. Chem. 1995, 60, 4024-4029.
61. Kolasa, T.; Miller, M. J. J. Org. Chem. 1987, 52, 4978-4984.
62. For related reactions, see: (a) Chapman, K T.; Kopka, I. E.; Durette, P. L.; Esser, C. K.; Lanza, T. J.; Izquierdo-Martin, M.; Niedzwiecki, L.; Chang, B.; Harrison, R. K; Kuo, D. W.; Lin, T.-Y.; Stein, R. L.; Hagmann, W. K. J. Med. Chem. 1993,36,4293-4301.
63. (b) Bird, J.; De Mello, R. C.; Harper, G. P.; Hunter, D. J.; Kamm, E. H.; Markwell, R. E.; Miles-Williams, A. J.; Rahman, S. S.; Ward, R. W. J. Med. Chem. 1994, 37, 158-169.
64. (a) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K B. J. Org. Chem. 1981,46, 3936-3938.
65. See also: (b) Godier-Marc, E.; Aitken, D. J.; Husson, H.-P. Tetrahedron Lett. 1997, 38, 4065-4068.
66. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151-2157.
67. Kaiser, C.; Weinstock, J. Org. Synth. 1988, 6, 910-913.
68. Roos, E. C.; Bernabe, P.; Hiemstra, H, Speckamp, W. N.; Kaptein, B.; Boesten, W. H. J. J. Org. Chem. 1995, 60, 1733-1740.
69. Bower, J. D.; Guest, K. P.; Morgan, B. A. J. Chem. Soc., Perkin 1 1976, 2488-2492.
70. Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495-496.
71. Olsen, R. K; Bhat, K. L.; Wardle, R. B.; Hennen, W. J.; Kini, G. D. J. Org. Chem. 1985, 50, 896-899.
72. Takano, S.; Yonaga, M.; Ogasawara, K Synthesis 1981, 265266.
73. Cheng, Y. C.; Prusoff, VV. H. Biochem. Pharmacol. 1973. 22, 3099-3108.
74. Paton, W. D. M.; Vizi, E. S. Br. J. Pharmacol. 1969, 35, 10-29.
75. Hughes, J.; Kosterlitz, H. W.; Leslie, F. M. Br. J. Pharmcol. 1975, 53, 371-381.
76. Ronai, A. Z.; Graf, L.; Szekely, J. I.; Dunai-Kovacs.'Z.; Bajusz, S. FEBS Lett. 1977, 74, 182-184.
77. (a) Belanger, P. C.; Dufresne, C.; Scheigetz, J.; Young, R. N.; Springer, J. P.; Dmitrienko, G. I. Can J. Chem. 1982, 60,1019-1029.
78. (b) Belanger, P. C.; Dufresne, C. Can. J. Chem. 1986, 64,1514-1520.
79. Claridge, T. D. W.; Hulme, C.; Kelly, R. J.; Lee, V.; Nash, I. A.; Schofield, C. J. Biorg. Med. Chem. Lett. 1996, 6, 485-490.
80. von Reedern, E. G.; Lohof, E.; Hessler, G.; Hofiman, M.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 10156-10167.
81. Christensen, J. J.; Izatt, R. M.; Wrathall, D. P.; Hansen, L. D. J. Chem. Soc. (A) 1969, 1212-1223.
82. Morley, J. S.; Dutta, A. S. Structure-Activity Relationships of Opiod Peptides. In Opioid Peptides: Medicinal Chemistry; NIDA Monograph 69; Rapaka, R. S.; Barnett, G.; Hawks, R. L., Eds., 1986; p 42-64.