MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

Journal of Organic Chemistry

Volumn 69, Issue 2, 2004, Pages 357-373

  Rodeschini, Vincent ^a   Boiteau, Jean Guy ^a   Van De Weghe, Pierre ^a   Tarnus, Céline ^a   Eustache, Jacques ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL);

RING-CLOSING METATHESIS;

ORGANIC COMPOUNDS;

ENZYME INHIBITOR; FUMAGILLIN; METHIONINE AMINOPEPTIDASE 2 INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

AMINOPEPTIDASES; ANGIOGENESIS INHIBITORS; CYCLOHEXANES; FATTY ACIDS, UNSATURATED; MAGNETIC RESONANCE SPECTROSCOPY; METALLOENDOPEPTIDASES; MODELS, MOLECULAR; SESQUITERPENES;

EID: 0347763342     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035065+     Document Type: Article

References (39)

1. Folkman, J. N. Engl. J. Med. 1971, 285, 1182-1185.
2. For reviews on the clinical potential of antiangiogenic agents, see: (a) Norrby, K. APMIS 1997, 105, 417-437.
3. (b) Liekens, S.; De Clercq, E.; Neyts, J. Biochem. Pharmacol. 2001, 61, 253-270.
4. (a) Liu, S.; Widom, J.; Kemp, C. W.; Crews, C. M.; Clardy, J. Science 1998, 282, 1324-1327.
5. (b) Sin, N.; Meng, L.; Wang, M. Q. W.; Wen, J. J.; Bornmann, W. G.; Crews, C. M. Proc. Natl. Acad. Sci. U.S.A. 1997 94, 6099-6103.
6. Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549-2550.
7. (a) Kim, D.; Ahn, S. K.; Bae, H.; Choi, W. J. Kim, H. S. Tetrahedron Lett. 1997, 38, 4437-4440.
8. (b) Taber, D. F.; Christos, T. E.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1999, 121, 5589-5590.
9. (c) Vosburg, D. A.; Weiler, S.; Sorensen, E. J. Angew. Chem., Int. Ed. 1999, 38, 971-974.
10. (d) Picoul, W.; Urchegui, R.; Haudrechy, A.; Langlois, Y. Tetrahedron Lett. 1999, 40, 4797-4800.
11. (e) Moffat, D.; Simpkins, N. S. Synlett 2001, 63-64.
12. (f) Boiteau, J.-G.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740.
13. (g) Vosburg, D. A.; Weiler, S.; Sorensen, E. J. Chirality 2003, 15, 156-66.
14. (h) Picoul, W.; Bedel, O.; Haudrechy, A.; Langlois, Y. Pure Appl. Chem. 2003, 75, 235-249.
15. Baldwin, J. E.; Bulger, P. G.; Marquez, R. Tetrahedron 2002, 58, 5441-5452.
16. (a) Griffith, E. C.; Su, Z.; Niwayama, S.; Ramsay, C. A.; Chang, Y.-H.; Liu, J. O. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15183-15188.
17. Lamothe, S.; Attardo, G.; Labrecque, D.; Courchesne, M.; Wang, W.; Li, T. WO 99/61142, 1999.
18. Han, C. K.; Ahn, S. K.; Choi, N. S.; Hong, R. K.; Moon, S. K.; Chun, H. S.; Lee, S. J.; Kim, J. W.; Hong, C. I.; Kim, D.; Yoon, J. H.; No, K. T. Bioorg. Med. Chem. Lett. 2000, 10, 39-43.
19. The validity of this approach has already been demonstrated in a preliminary communication (ref 5f).
20. Rand, C. L.; Van Horn, D. E.; Moore, M. W.; Negishi, E. J. Org. Chem. 1981, 46, 4093-4096.
21. Weissberger, E.; Stockis, A.; Carr, D. D.; Gienfried, J. Bull. Soc. Chim. Belg. 1980, 89, 281-288.
22. Although aldehyde 12 is a 7.7: 1 mixture of (R) and (S) enantiomers, we could isolate only one aldol product, after deselenylation. This unexpected result has also been observed in the course of our fumagillol synthesis (see ref 5f) as well as with other similar condensations using aldehyde 12 and oxazolidinones bearing branched, β,γ-unsaturated acyl groups (unpublished results). A possible explanation is that of preferential condensation of these oxazolidinones with (S)-12 possibly due to "matched" double-asymmetric induction, whereas reaction with (R)-12 would be kinetically strongly disfavoured. Although we are not aware of literature reports fully supporting our tentative explanation, a related behavior of oxazolidinone boron enolates was described: Sibi, M. P.; Lu, J.; Talbacka, C. L. J. Org. Chem. 1996, 61, 7848-7855. In this report, however, the differences in yields were not as marked as in the present work.
23. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Meneses, R. Synlett 1999, 1663-1666.
24. Amano, S.; Ogawa, M.; Ohtsuka, M.; Childa, N. Tetrahedron 1999, 55, 2205-2224.
25. In related side chain-modified fumagillin analogues, epoxidation always occurs on the re-re face of the 1′,2′ olefinic double bond to afford the (1′R,2′R) epoxide in large excess. See refs 4, 5a, 5b.
26. 50 were determined by incubating the enzyme and its substrate (following the experimental conditions described above) with increasing concentrations of inhibitor.
27. Li, X.; Chang, Y.-H. Biochem. Biophys. Res. Commun. 1996, 227, 152-159
28. Ben-Bassat, A.; Bauer, K.; Chang, S. Y.; Myambo, K.; Boosman, A.; Chang, S. J. Bacteriol. 1987, 169, 751-757.
29. (a) Solomon, M.; Jamison, W. C. L.; McCormick, M.; Liotta, D. C.; Cherry, D. A.; Mills, J. E.; Shah, R. D.; Rodgers, J. D.; Maryanoff, C A. J. Am. Chem. Soc. 1988, 110, 3702-3704.
30. (b) Swiss, K. A.; Hinkley, W.; Maryanoff, C. A.; Liotta, D. C. Synthesis 1992, 127-131.
31. (a) Carreño, M. C.; Perez-Gonzalez, M.; Ribagorda, M.; Houk, K. N. J. Org. Chem. 1998, 63, 3687-3693.
32. (b) Carreño M. C.; Perez-Gonzalez, M.; Ribagorda M.; Fisher, J. J. Org. Chem. 1996, 61, 6758-6759.
33. Attempted epoxidation of alcohol 33 led to the exclusive formation of a cyclopropyl ketone as observed earlier. Facile intramolecular deprotonation by the alcoolate derived from OH-6 followed by β-elimination of the methoxy group may explain this result. During this work, this type of β-elimination constantly constituted a potential problem which required particular attention.
34. Miyashita, M.; Suzuki, T.; Hoshino, M.; Yoshikoshi, A. Tetrahedron 1997, 53, 12469-12486.
35. The alternative TBHP/triton B method led to erratic results (yields ranging from 25% to 75%) the major problem being the oxidation of the PMB group to the corresponding p-methoxybenzoate.
36. On the basis of literature precedents, the epoxide function was expected to be located trans to the OPMB group: Barros, M. T.; Maycock, C. D.; Ventura, M. R. J. Org. Chem. 1997, 62, 3984-3988.
37. (a) Kabat, M. M.; Kiegel, J.; Cohen, N.; Toth, K.; Wovkulich, P. M.; Uskokovíc, M. R. J. Org. Chem. 1996, 61, 118-124.
38. (b) Taylor, R. J. K.; Thorsten, G. Tetrahedron Lett. 2002, 43, 3573-3576.
39. Liu, H.-J.; Browne, E. N. C. Can. J. Chem. 1980, 59, 601-607.