Probing the importance of spacial and conformational domains in captopril analogs for angiotensin converting enzyme activity

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 16, 1998, Pages 2123-2128

  Hanessian, Stephen ^a   Reinhold, Ulrich ^a   Saulnier, Michel ^a   Claridge, Stephen ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4,5 METHANOPROLINE DERIVATIVE; CAPTOPRIL; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; N (3 MERCAPTO 2 METHYLPROPIONYL) DERIVATIVE; RAMIPRILAT; UNCLASSIFIED DRUG;

ANTIHYPERTENSIVE THERAPY; ARTICLE; DRUG CONFORMATION; DRUG DESIGN; HYPERTENSION;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; ANIMALS; CAPTOPRIL; DRUG DESIGN; INDICATORS AND REAGENTS; ISOMERISM; LUNG; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PEPTIDYL-DIPEPTIDASE A; PROLINE; RABBITS; RAMIPRIL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032544133     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00377-1     Document Type: Article

References (31)

1. 1. For excellent summaries, see Burger's Medicinal Chemistry and Drug Discovery, Wiley-Interscience, N. Y., 1995. Muscate, A.; Kenyon, G. L., p 739; Cannon, J. G., p 783.
2. 2. (a) Ondetti, M. A.; Cushman, D. W. J. Med. Chem. 1981, 24, 355;
3. (b) Cushman, D. W.; Ondetti, M. A. Prog. Med. Chem. 1980, 17, 41.
4. (c) Patchett, A. A.; Harris, E.; Tristram, E. W.; Wyvratt, M. I.; Wu, M. T.; Taub, D.; Peterson, E. R.; Ikeler, T. J.; ten Broeke, J.; Payne, L. G.; Ondeyka, D. L.; Thorsett, E. D.; Greenlee, W. J.; Lohr, N. S.; Hoffsommer, R. D.; Joshua, H.; Ruyle, W. V.; Rothrock, J. W.; Aster, S. D.; Maycock, A. L.; Robinson, F. M.; Hirschmann, R.; Sweet, C. S.; Ulm, E. H.; Gross, D. M.; Vassil, T. C.; Stone, C. A. Nature 1980, 288, 280.
5. 3. Ondetti, M. A.; Rubin, B.; Cushman, D. W. Science 1977, 196, 441; Cushman, D. W.; Cheung, H. S.; Sabo, F. C.; Ondetti, M. A. Biochemistry 1977, 16, 5484.
6. 3. Ondetti, M. A.; Rubin, B.; Cushman, D. W. Science 1977, 196, 441; Cushman, D. W.; Cheung, H. S.; Sabo, F. C.; Ondetti, M. A. Biochemistry 1977, 16, 5484.
7. 4. Urbach, H.; Henning, R. Tetrahedron Lett. 1985, 26, 1839; Henning, R.; Urbach, H. Tetrahedron Lett. 1983, 24, 5339; Teetz, V.; Geiger, R.; Henning, R.; Urbach, H. Arzneim. Forsch./Drug Res. 1984, 34, 1399.
8. 4. Urbach, H.; Henning, R. Tetrahedron Lett. 1985, 26, 1839; Henning, R.; Urbach, H. Tetrahedron Lett. 1983, 24, 5339; Teetz, V.; Geiger, R.; Henning, R.; Urbach, H. Arzneim. Forsch./Drug Res. 1984, 34, 1399.
9. 4. Urbach, H.; Henning, R. Tetrahedron Lett. 1985, 26, 1839; Henning, R.; Urbach, H. Tetrahedron Lett. 1983, 24, 5339; Teetz, V.; Geiger, R.; Henning, R.; Urbach, H. Arzneim. Forsch./Drug Res. 1984, 34, 1399.
10. 5. Hanessian, S.; Reinhold, U.; Gentile, G. Angew. Chem. Int. Ed. Engl. 1997, 36, 1881.
11. 6. Hanessian, S.; Reinhold, U.; Ninkovic, S. Tetrahedron Lett. 1996, 37, 8967; 8971.
12. 7. For the synthesis of racemic and enantiopure 2,3-methano proline, see (a) Hercouet, A.; Bessières, B., Le Corre, M. Tetrahedron: Asymmetry 1996, 7, 1267.
13. (b) Switzer, F. L.; van Halbeek, H.; Holt, E. M.; Stammer, C. H. Tetrahedron 1989, 45, 6091. For recent accounts on 2,3-methano amino acids, see: Stammer, C. H. Tetrahedron 1990, 46, 2231; Burgess, K.; Ho, K. K.; Moyl-Sherman, D. Synlett 1994, 575; Burgess, K.; Ke, C.-Y. J. Org. Chem. 1996, 61, 8627. Jiménez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1996, 7, 3203, and references cited therein.
14. (b) Switzer, F. L.; van Halbeek, H.; Holt, E. M.; Stammer, C. H. Tetrahedron 1989, 45, 6091. For recent accounts on 2,3-methano amino acids, see: Stammer, C. H. Tetrahedron 1990, 46, 2231; Burgess, K.; Ho, K. K.; Moyl-Sherman, D. Synlett 1994, 575; Burgess, K.; Ke, C.-Y. J. Org. Chem. 1996, 61, 8627. Jiménez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1996, 7, 3203, and references cited therein.
15. (b) Switzer, F. L.; van Halbeek, H.; Holt, E. M.; Stammer, C. H. Tetrahedron 1989, 45, 6091. For recent accounts on 2,3-methano amino acids, see: Stammer, C. H. Tetrahedron 1990, 46, 2231; Burgess, K.; Ho, K. K.; Moyl-Sherman, D. Synlett 1994, 575; Burgess, K.; Ke, C.-Y. J. Org. Chem. 1996, 61, 8627. Jiménez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1996, 7, 3203, and references cited therein.
16. (b) Switzer, F. L.; van Halbeek, H.; Holt, E. M.; Stammer, C. H. Tetrahedron 1989, 45, 6091. For recent accounts on 2,3-methano amino acids, see: Stammer, C. H. Tetrahedron 1990, 46, 2231; Burgess, K.; Ho, K. K.; Moyl-Sherman, D. Synlett 1994, 575; Burgess, K.; Ke, C.-Y. J. Org. Chem. 1996, 61, 8627. Jiménez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1996, 7, 3203, and references cited therein.
17. (b) Switzer, F. L.; van Halbeek, H.; Holt, E. M.; Stammer, C. H. Tetrahedron 1989, 45, 6091. For recent accounts on 2,3-methano amino acids, see: Stammer, C. H. Tetrahedron 1990, 46, 2231; Burgess, K.; Ho, K. K.; Moyl-Sherman, D. Synlett 1994, 575; Burgess, K.; Ke, C.-Y. J. Org. Chem. 1996, 61, 8627. Jiménez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1996, 7, 3203, and references cited therein.
18. 8. For the synthesis of cis- and trans-3,4-methano prolines, see (a) Fujimoto, Y.; Irrevere, F.; Karle, J. M.; Karle, I. L.; Witkop, B. J. Am. Chem. Soc. 1971, 93, 3471; for a recent discussion of cyclopropyl pyrrolidines, see Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268; Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097.
19. 8. For the synthesis of cis- and trans-3,4-methano prolines, see (a) Fujimoto, Y.; Irrevere, F.; Karle, J. M.; Karle, I. L.; Witkop, B. J. Am. Chem. Soc. 1971, 93, 3471; for a recent discussion of cyclopropyl pyrrolidines, see Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268; Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097.
20. 8. For the synthesis of cis- and trans-3,4-methano prolines, see (a) Fujimoto, Y.; Irrevere, F.; Karle, J. M.; Karle, I. L.; Witkop, B. J. Am. Chem. Soc. 1971, 93, 3471; for a recent discussion of cyclopropyl pyrrolidines, see Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268; Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097.
21. 9. For the synthesis of racemic 4,5-methano proline amides, see a) H. Urbach, R. Henning, R. Becker, Ger. Offen. DE 3,324,263 (Cl. C07D209/2); Chem. Abstr. 1985, 103: P 54461q; for a related example involving mixtures of diastereomers, see also R. Pellicciari, L. Arenare, P. De Caprariis, B. Natalin, M. Marinozzi, A. Galli, J. Chem. Soc. Perkin 1. 1995, 1251.
22. 9. For the synthesis of racemic 4,5-methano proline amides, see a) H. Urbach, R. Henning, R. Becker, Ger. Offen. DE 3,324,263 (Cl. C07D209/2); Chem. Abstr. 1985, 103: P 54461q; for a related example involving mixtures of diastereomers, see also R. Pellicciari, L. Arenare, P. De Caprariis, B. Natalin, M. Marinozzi, A. Galli, J. Chem. Soc. Perkin 1. 1995, 1251.
23. 10. Shono, T.; Matsumura, Y.; Tsubata, K.; Sugihara, Y.; Yamane, S. I.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697.
24. 11. Typical procedure: A mixture containing N-Boc-5-methoxy-(2S)-pyrrolidine-1-carboxylic acid ethyl ester (1.2 g, 4.4 mmol) and ammonium chloride (0.044 g, 0.15 equiv) was heated under reduced pressure (20-100 mm Hg) in a flask equipped with a reflux condenser. The reaction mixture was allowed to cool to room temperature, and the resultant oil was purified by flash chromatography on silica gel (hexanes-ethyl acetate, 9:1) to afford the product 12 (0.854 g, 81%) as a colorless oil.
25. 12. Dieter, R.K.; Sharma, R.R. J. Org. Chem. 1996, 61, 4180; Cossy, J.; Cases, M.; Pardo, D.G. Syn. Commun. 1997, 27, 2769.
26. 12. Dieter, R.K.; Sharma, R.R. J. Org. Chem. 1996, 61, 4180; Cossy, J.; Cases, M.; Pardo, D.G. Syn. Commun. 1997, 27, 2769.
27. 13. Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53.
28. 2), and separated by chromatograhy to give 13 and 14 (75% yield, 1:4 ratio).
29. 15. For related examples of directed cyclopropanations see, Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197; For examples of proximity effects, see Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
30. 15. For related examples of directed cyclopropanations see, Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197; For examples of proximity effects, see Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
31. 16. Cushman, D. W.; Cheung, H. S. Biochem. Pharmacol. 1971, 20, 1637.