Diastereoselective solution and multipin-based combinatorial array synthesis of a novel class of potent phosphinic metalloprotease inhibitors

Chemistry - A European Journal

Volumn 9, Issue 9, 2003, Pages 2079-2094

  Makaritis, Anastasios ^a   Georgiadis, Dimitris ^a   Dive, Vincent ^b   Yiotakis, Athanasios ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b DIF   (France)

Author keywords

Combinatorial chemistry; Cycloaddition; Inhibitors; Metalloproteins; Solid phase synthesis

Indexed keywords

NUCLEAR MAGNETIC RESONANCE; OPTIMIZATION; SOLUTIONS; SYNTHESIS (CHEMICAL);

DIASTEREOSELECTIVE SOLUTIONS;

ORGANOMETALLICS;

1 [[(BENZYLOXY)CARBONYL]AMINO] 2 PHENYLETHYL [3 [[2 METHOXY 1 METHYL 2 OXOETHYL]AMINO] 2 [[3 (4 NITROPHENYL)ISOXAZOL 5 YL]METHYL] 3 OXOPROPYL]PHOSPHINIC ACID; 1 [[(BENZYLOXY)CARBONYL]AMINO] 2 PHENYLETHYL [3 [[2 METHOXY 1 METHYL 2 OXOETHYL]AMINO] 3 OXO 2 [(3 PHENYLISOXAZOL 5 YL)METHYL]PROPYL]PHOSPHINIC ACID; 3 [[2 AMINO 1 (1H INDOL 3 YLMETHYL) 2 OXOETHYL]AMINO] 2 [(3 NONYLISOXAZOL 5 YL)METHYL] 3 OXOPROPYL [1 [[(BENZYLOXY)CARBONYL]AMINO] 2 PHENYLETHYL]PHOSPHINIC ACID; 3 [[2 AMINO 1 (1H INDOL 3 YLMETHYL) 2 OXOETHYL]AMINO] 2 [[3 (1,1' BIPHENYL) 4 YLISOXAZOL 5 YL]METHYL] 3 OXOPROPYL 1 [[[(BENZYLOXY)CARBONYL]AMINO]ETHYL]PHOSPHINIC ACID; 3 [[2 AMINO 1 (1H INDOL 3 YLMETHYL) 2 OXOETHYL]AMINO] 2 [[3 (2 FURYL)ISOXAZOL 5 YL]METHYL] 3 OXOPROPYL [[[(BENZYLOXY)CARBONYL]AMINO](PHENYL)METHYL]PHOSPHINIC ACID; 3 [[2 AMINO 1 (1H INDOL 3 YLMETHYL) 2 OXOETHYL]AMINO] 2 [[3 (2 NAPHTHYL)ISOXAZOL 5 YL]METHYL] 3 OXOPROPYL [1 [[(BENZYLOXY)CARBONYL]AMINO] 2 PHENYLETHYL]PHOSPHINIC ACID; 3 [[2 AMINO 1 (1H INDOL 3 YLMETHYL) 2 OXOETHYL]AMINO] 2 [[3 (4 FLUOROPHENYL)ISOXAZOL 5 YL]METHYL] 3 OXOPROPYL [[[(BENZYLOXY)CARBONYL]AMINO](PHENYL)METHYL]PHOSPHINIC ACID; 3 [[2 AMINO 1 (1H INDOL 3 YLMETHYL) 2 OXOETHYL]AMINO] 3 OXO 2 [(3 PHENYLISOXAZOL 5 YL)METHYL]PROPYL [1 [[(BENZYLOXY)CARBONYL]AMINO] 2 PHENYLETHYL]PHOSPHINIC ACID; 3 [[2 AMINO 1 (1H INDOL 3 YLMETHYL) 2 OXOETHYL]AMINO] 3 OXO 2 [[3 (3 PHENOXYPHENYL)ISOXAZOL 5 YL]METHYL]PROPYL [1 [[(BENZYLOXY)CARBONYL]AMINO] 2 PHENYLETHYL]PHOSPHINIC ACID; ISOXAZOLE DERIVATIVE; METALLOPROTEINASE INHIBITOR; NITRILE; PEPTIDE DERIVATIVE; PHOSPHINIC ACID DERIVATIVE; PSEUDOPEPTIDE; RXP 03; UNCLASSIFIED DRUG;

ARTICLE; COMBINATORIAL CHEMISTRY; CYCLOADDITION; DIASTEREOISOMER; DRUG DETERMINATION; DRUG POTENCY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; OPTICAL ROTATION; STEREOCHEMISTRY;

COLLAGENASES; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDICATORS AND REAGENTS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MATRIX METALLOPROTEINASE 13; MATRIX METALLOPROTEINASE 3; MATRIX METALLOPROTEINASES, MEMBRANE-ASSOCIATED; METALLOENDOPEPTIDASES; PHOSPHINIC ACIDS; PROTEASE INHIBITORS; SOLUTIONS; STEREOISOMERISM;

EID: 0037799599     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204456     Document Type: Article

References (93)

1. a) B. P. Morgan, J. M. Scholtz, M. D. Billinger, I. D. Zipkin, P. A. Bartlett, J. Am. Chem. Soc. 1991, 113, 297-307;
2. b) N. E. Jacobsen, P. A. Bartlett, J. Am. Chem. Soc. 1981, 103, 654-657;
3. c) P. A. Bartlett, C. K. Marlowe, Biochemistry 1983, 22, 4618-4624;
4. d) K. A. Mookhtiar, C. K. Marlowe, P. A. Bartlett, H. E. Van Wart, Biochemistry 1987, 26, 1962-1965:
5. e) P. P. Giannousis, P. A. Bartlett, J. Med. Chem. 1987, 30, 1603-1609.
6. a) M. Collinsova, J. Jiracek, Curr. Med. Chem. 2000, 7, 629-647, and references therein;
7. b) J. E. Hanson, A. P. Kaplan, P. A. Bartlett, Biochemistry 1989, 28, 6294-6305;
8. c) A. Yiotakis, A. Lecoq, A. Nicolaou, J. Labadie, V. Dive, Biochem. J. 1994, 303, 323-327;
9. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity (Eds.: V. P. Kukhar, H. R. Hudson), Wiley, Chicester, 2000.
10. a) F. Grams, V. Dive, A. Yiotakis, I. Yiallouros, S. Vassiliou, R. Zwilling, W. Bode, W. Stöcker, Nat. Struct. Biol. 1996, 3, 671-675;
11. b) V. Dive, K. Lucet-Levannier, D. Georgiadis, J. Cotton, S. Vassiliou, P. Cuniasse, A. Yiotakis, Biochem. Soc. Trans. 2000, 28, 455-460.
12. a) J. Buchardt, M. Ferreras, C. Krog-Jensen, J.-M. Delaisse, N. T. Foged, M. Meldal, Chem. Eur. J. 1999, 5, 2877-2884;
13. b) S. Vassiliou, A. Mucha, P. Cuniasse, D. Georgiadis, K. Lucet-Levannier, F. Beau, R. Kannan, G. Murphy, V. Knäuper, M.-C. Rio, P. Basset, A. Yiotakis, V. Dive, J. Med. Chem. 1999, 42, 2610-2620;
14. c) J. Buchardt, C. B. Schiodt, C. Krog-Jensen, J.-M. Delaisse, N. T. Foged, M. Meldal, J. Comb. Chem. 2000, 2, 624-638.
15. d) C. G. Caldwell, S. P. Sahoo, S. A. Polo, R. R. Eversole, T. J. Lanza, S. G. Mills, L. M. Niedzwiecki, M. Izquierdo-Martin, B. C. Chang, R. K. Harrison, D. W. Kuo, T.-Y. Lin, R. L. Stein, P. L. Durette, W. K. Hagmann, Bioorg. Med. Chem. Lett. 1996, 6, 323-328;
16. e) L. A. Reiter, J. P. Rizzi, J. Pandit, M. J. Lasut, S. M. McGahee, V. D. Parikh, J. F. Blake, D. E. Danley, E. R. Laird, A. Lopez-Anaya, L. L. Lopresti-Morrow, M. N. Mansour, G. J. Martinelli, P. G. Mitchell, B. S. Owens, T. A. Pauly, L. M. Reeves, G. K. Schulte, A. S. Yocum, Bioorg. Med. Chem. Lett. 1999, 9, 127-132.
17. A. Yiotakis, A. Lecoq, S. Vassiliou, I. Raynal, P. Cuniasse, V. Dive, J. Med. Chem. 1994, 37, 2713-2720.
18. a) H. Chen, F. Noble, A. Yiotakis, A. Makaritis, P. George, B. P. Roques, M.-C. Fournie Zaluski in Peptides 2000 (Eds.: J. Martinez, J.-A. Fehrentz), EDK, Paris, France, 2001, pp. 365-366;
19. b) H. Chen, F. Noble, A. Mothe, H. Meudal, P. Coric, S. Danascimento, B. P. Roques, P. George, M.-C. Fournie Zaluski, J. Med. Chem. 2000, 43, 1398-1408;
20. c) A. Makaritis, B. P. Roques, M.-C. Fournie Zaluski, M. Matziari, D. Georgiadis, A. Yiotakis in 2nd Hellenic Forum on Bioactive Peptides (Ed.: P. Cordopatis), Typorama, Patras, Greece, 2001, pp. 291-296.
21. a) D. Grobelny, U. B. Goli, R. E. Galardy, Biochemistry 1989, 28, 4948-4951;
22. b) J. Jiracek, A. Yiotakis, B. Vincent, F. Checler, V. Dive, J. Biol. Chem. 1996, 271, 19606-19611;
23. c) J. Jiracek, A. Yiotakis, B. Vincent, A. Lecoq, A. Nicolaou, F. Checler, V. Dive, J. Biol. Chem. 1995, 270, 21701-21706;
24. d) B. A. McKittrick, A. W. Stamford, X. Weng, K. Ma, S. Chackalamannil, M. Czarniecki, R. M. Cleven, A. B. Fawzi, Bioorg. Med. Chem. Lett. 1996, 6, 1629-1634.
25. a) D. Grobelny, E. M. Wondrak, R. E. Galardy, S. Oroszlan, Biochem. Biophys. Res. Commun. 1990, 169, 1111-1116;
26. b) A. Peyman, K. Wagner, K.-H. Budt, J. Spanig, D. Ruppert, C. Meichsner, A. Paessens, Bioorg. Med. Chem. Lett. 1994, 4, 1191-1194.
27. a) D. J. Miller, S. M. Hammond, D. Anderluzzi, T. D. H. Bugg, J. Chem. Soc. Perkin Trans. 1 1998, 131-142;
28. b) N. Valiaeva, D. Bartley, T. Konno, J. K. Coward, J. Org. Chem. 2001, 66, 5146-5154.
29. V. Dive, J. Cotton, A. Yiotakis, A. Michaud, S. Vassiliou, J. Jiracek, G. Vazeux, M. T. Chauvet, P. Cuniasse, P. Corvol, Proc. Natl. Acad. Sci. USA 1999, 96, 4330-4335.
30. a) R. Cursio, B. Mari, K. Louis, P. Rostagno, M.-C. Saint-Paul, J. Giudicelli, V. Bottero, P. Anglard, A. Yiotakis, V. Dive, J. Gugenheim, P. Auberger, FASEB J. 2002, 16, 93-95;
31. b) C. Junot, M. F. Gonzales, E. Ezan, J. Cotton, G. Vazeux, A. Michaud, M. Azizi, S. Vassiliou, A. Yiotakis, P. Corvol, V. Dive, J. Pharmacol. Exp. Ther. 2001, 297, 606-611;
32. c) G. Vazeux, J. Cotton, P. Cuniasse, V. Dive, Biochem. Pharmacol. 2001, 61, 835-841.
33. M. Whittaker, C. D. Floyd, P. Brown, A. J. H. Gearing, Chem. Rev. 1999, 99, 2735-2776.
34. A.-L. Gall, M. Ruff, R. Kannan, P. Cuniasse, A. Yiotakis, V. Dive, M.-C. Rio, P. Basset, D. Moras, J. Mol. Biol. 2001, 307, 577-586.
35. D. Georgiadis, M. Matziari, S. Vassiliou, V. Dive, A. Yiotakis, Tetrahedron 1999, 55, 14635-14648.
36. a) A. Yiotakis, S. Vassiliou, J. Jiracek, V. Dive, J. Org. Chem. 1996, 61, 6601-6605;
37. b) J. K. Thottathil, D. E. Ryono, C. A. Przybyla, J. L. Moniot, R. Neubeck, Tetrahedron Lett. 1984, 25, 4741-4744;
38. c) E. A. Boyd, A. C. Regan, K. James, Tetrahedron Lett. 1992, 33, 813-816.
39. M. Matziari, D. Georgiadis, V. Dive, A. Yiotakis, Org. Lett. 2001, 3, 659-662.
40. a) S. Kanemasa, O. Tsuge, Heterocycles 1990, 30, 719-736;
41. b) E. W. Collington, J. G. Knight, C. J. Wallis, S. Warren, Tetrahedron Lett. 1989, 30, 877-880;
42. c) A. P. Kozikowski, M. Adamczyk, J. Org. Chem. 1983, 48, 366-372;
43. d) P. G. Baraldi, A. Barco, S. Benetti, G. P. Pollini, D. Simoni, Synthesis 1987, 857-869.
44. a) R. C. F. Jones, S. J. Hollis, J. N. Iley, Tetrahedron: Asymmetry 2000, 11, 3273-3276;
45. b) L. De Luca, G. Giacomelli, A. Riu, J. Org. Chem. 2001, 66, 6823-6825.
46. a) M. Rowley, H. B. Broughton, I. Collins, R. Baker, F. Emms, R. Marwood, S. Patel, S. Patel, C. I. Ragan, S. B. Freedman, P. D. Leeson, J. Med. Chem. 1996, 39, 1943-1945;
47. b) D. Simoni, F. P. Invidiata, R. Rondanin, S. Grimaudo, G. Cannizzo, E. Barbusca, F. Porretto, N. D'Alessandro, M. Tolomeo, J. Med. Chem. 1999, 42, 4961-4969;
48. c) J. J. Talley, D. L. Brown, J. S. Carter, M. J. Graneto, C. M. Koboldt, J. L. Masferrer, W. E. Perkins, R. S. Rogers, A. F. Shaffer, Y. Y. Zhang, B. S. Zweifel, K. Seibert, J. Med. Chem. 2000, 43, 775-777;
49. d) R. Riess, M. Schön, S. Laschat, V. Jäger, Eur. J. Org. Chem. 1998, 473-479;
50. e) D. Simoni, M. Roberti, F. P. Invidiata, R. Rondanin, R. Baruchello, C. Malagutti, A. Mazzali, M. Rossi, S. Grimaudo, F. Capone, L. Dusonchet, M. Meli, M. V. Raimondi, M. Landino, N. D'Alessandro, M. Tolomeo, D. Arindam, S. Lu, D. M. Benbrook, J. Med. Chem. 2001, 44, 2308-2318;
51. f) Y. Kanda, T. Takahashi, Y. Araki, T. Konoike, S. Mihara, M. Fujimoto, Bioorg. Med. Chem. Lett. 2000, 10, 1875-1878;
52. g) U. Mangold, C. I. Dax, K. Saar, W. Schwab, B. Kirschbaum, S. Mullner, Eur. J. Biochem. 1999, 266, 1184-1191;
53. h) P. Pevarello, R. Amici, M. G. Basca, M. Ville, M. Varasi, Targets Heterocycl. Sys. 1999, 3, 301-339.
54. T. L. Gilchrist, Heterocyclic Chemistry, 2nd ed., Longman Scientific & Technical (UK), 1993, pp. 314-321, and references therein.
55. a) M. Massacesi, G. Ponticelli, C. Preti, J. Inorg. Nucl. Chem. 1975, 37, 1641-1645;
56. b) M. Massacesi, G. Ponticelli, C. Preti, J. Inorg. Nucl. Chem. 1976, 38, 1556-1557;
57. c) E. J. Kantorowski, M. J. Kurth, J. Org. Chem. 1997, 62, 6797-6803;
58. d) R. E. Sammelson, R. B. Miller, M. J. Kurth, J. Org. Chem. 2000, 65, 2225-2228.
59. P. Caramella, P. Grunanger in 1,3-Dipolar Cycloaddition Chemistry, Vol. 1 (Ed.: A. Padwa), Wiley, New York, 1984, pp. 291-392.
60. H. Stetter, H. Kuhlmann, Synthesis 1979, 29-30.
61. E. K. Baylis, C. D. Campbell, J. G. Dingwall, J. Chem. Soc. Perkin Trans. 1 1984, 2845-2853.
62. X. Liu, X. E. Hu, X. Tian, A. Mazur, F. H. Ebetino, J. Organomet. Chem. 2002, 646, 212-222.
63. L. A. Reiter, B. P. Jones, J. Org. Chem. 1997, 62, 2808-2812.
64. H. Lindlar, R. Dubuis, F. N. Jones, B. C. McKusick, Org. Synth. 1966, 46, 880-883.
65. P. S. Dragovich, R. Zhou, D. J. Skalitzky, S. A. Fuhrman, A. K. Patick, C. E. Ford, J. W. Meador, III, S. T. Worland, Bioorg. Med. Chem. 1999, 7, 589-598.
66. T. L. Gilchrist, Heterocyclic Chemistry, 2nd ed., Longman Scientific & Technical (UK), 1993, pp. 87-103.
67. T. Mukaiyama, T. Hoshino, J. Am. Chem. Soc. 1960, 82, 5339-5342.
68. G. A. Lee, Synthesis 1982, 508-509.
69. a) M. Christl, R. Huisgen, Chem. Ber. 1973, 3345-3367; for modifications and improved versions of the method see: b) K.-C. Liu, B. R. Shelton, R. K. Howe, J. Org. Chem. 1980, 45, 3916-3918; c) K. E. Larsen, K. B. G. Torssell, Tetrahedron 1984, 40, 2985-2988.
70. a) M. Christl, R. Huisgen, Chem. Ber. 1973, 3345-3367; for modifications and improved versions of the method see: b) K.-C. Liu, B. R. Shelton, R. K. Howe, J. Org. Chem. 1980, 45, 3916-3918; c) K. E. Larsen, K. B. G. Torssell, Tetrahedron 1984, 40, 2985-2988.
71. a) M. Christl, R. Huisgen, Chem. Ber. 1973, 3345-3367; for modifications and improved versions of the method see: b) K.-C. Liu, B. R. Shelton, R. K. Howe, J. Org. Chem. 1980, 45, 3916-3918; c) K. E. Larsen, K. B. G. Torssell, Tetrahedron 1984, 40, 2985-2988.
72. A. P. Kozikowski, K. Sato, A. Basu, J. S. Lazo, J. Am. Chem. Soc. 1989, 111, 6228-6234.
73. P. H. H. Hermkens, H. C. J. Ottenheijm, D. C. Rees, Tetrahedron 1997, 53, 5643-5678;
74. J. Lloyd, J. B. Schmidt, J. T. Hunt, J. C. Barrish, D. K. Little, A. A. Tymiak, Bioorg. Med. Chem. Lett. 1996, 6, 1323-1326.
75. a) D. Georgiadis, M. Matziari, A. Yiotakis, Tetrahedron 2001, 57, 3471-3478; for a different approach see: b) J. Buchardt, M. Meldal, J. Chem. Soc. Perkin Trans. 1 2000, 3306-3310.
76. a) D. Georgiadis, M. Matziari, A. Yiotakis, Tetrahedron 2001, 57, 3471-3478; for a different approach see: b) J. Buchardt, M. Meldal, J. Chem. Soc. Perkin Trans. 1 2000, 3306-3310.
77. R. G. Franzen, J. Comb. Chem. 2000, 2, 195-214.
78. a) K.-H. Park, M. J. Kurth, J. Org. Chem. 1999, 64, 9297-9300;
79. b) B. B. Shankar, D. Y. Yang, S. Girton, A. K. Ganguly, Tetrahedron Lett. 1998, 39, 2447-2448;
80. c) K.-H. Park, M. J. Kurth, Tetrahedron Lett. 1999, 40, 5841-5844;
81. d) D.-M. Shen, M. Shu, K. T. Chapman, Org. Lett. 2000, 2, 2789-2792;
82. e) A. G. M. Barrett, P. A. Procopiou, U. Voigtmann, Org. Lett. 2001, 3, 3165-3168.
83. J.-M. Campagne, J. Coste, L. Guillou, A. Heitz, P. Jouin, Tetrahedron Lett. 1993, 34, 4181-4184.
84. Information and helpful hints can be found at: http://www.mimotopes.com
85. a) K.-H. Park, J. Ehrler, H. Spoerri, M. J. Kurth, J. Comb. Chem. 2001, 3, 171-176;
86. b) for discussion of the advantages of pins over resins see: SynPhase Technical Notes (STN 001-1) pp. 1-8, at: http://www.mimotopes.com
87. T. Miyazawa, T. Otomatsu, Y. Fukui, T. Yamada, S. Kuwata, J. Chem. Soc. Chem. Commun. 1988, 419-420.
88. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity (Eds.: V. P. Kukhar, H. R. Hudson), Wiley, Chicester, 2000, pp. 285-325, and references therein.
89. J. M. Freije, I. Diez-Itza, M. Balbin, L. M. Sanchez, R. Blasco, J. Tolivia, C. Lopez-Otin, J. Biol. Chem. 1994, 269, 16766-16773.
90. C. M. Overall, C. Lopez-Otin, Nat. Rev. Cancer 2002, 2, 657-672.
91. L. M. Coussens, B. Fingleton, L. M. Matrisian, Science 2002, 295, 2387-2392.
92. M. Egeblad, Z. Werb, Nat. Rev. Cancer 2002, 2, 161-174.
93. A. I. Vogel in VOGEL's Text Book of Practical Organic Chemistry (Ed.: A. I. Vogel), Longman, London, 1989, pp. 1259 and 1332-1335.