Enantio- and diastereoselective total synthesis of EI-1941-1, -2, and -3, inhibitors of interleukin-1β converting enzyme, and biological properties of their derivatives

Journal of Organic Chemistry

Volumn 70, Issue 24, 2005, Pages 9905-9915

  Shoji, Mitsuru ^a   Uno, Takao ^a   Kakeya, Hideaki ^b   Onose, Rie ^b   Shiina, Isamu ^a   Osada, Hiroyuki ^b   Hayashi, Yujiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SELECTIVITY; DERIVATIVES; ENZYMES; HYDRIDES; KETONES; SYNTHESIS (CHEMICAL);

CARBOXYPALLADATION; CYCLIZATION; CYTOTOXICITY; DIASTEREOSELECTIVITY;

ENZYME INHIBITION;

CARBOXYL GROUP; EI 1941 1; EI 1941 2; EI 1941 3; ENZYME INHIBITOR; EPOXIDE; EPOXYIODOQUINONE; EPOXYQUINOL A; EPOXYQUINOL B; INTERLEUKIN 1BETA CONVERTING ENZYME; INTERLEUKIN 1BETA CONVERTING ENZYME INHIBITOR; PALLADIUM; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL CULTURE; CELL LINE; CHIRALITY; CULTURE MEDIUM; CYCLIZATION; CYTOTOXICITY; DIASTEREOISOMER; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

CASPASE 1; CELL LINE; CELL SURVIVAL; CYCLOHEXANONES; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; EPOXY COMPOUNDS; HETEROCYCLIC COMPOUNDS, 2-RING; HUMANS; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 28044469310     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0516436     Document Type: Article

References (62)

1. (a) Dinarello, C. A. Blood 1991, 77, 1627.
2. (b) Dinarello, C. A.; Wolff, S. M. N. Engl. J. Med. 1993, 328, 106.
3. (a) Thornberry, N. A.; Bull, H. G.; Calaycay, J. R.; Chapman, K. T.; Howard, A. D.; Kostura, M. J.; Miller, D. K.; Molineaux, S. M.; Weidner, J. R.; Aunins, J.; Elliston, K. O.; Ayala, J. M.; Casano, F. J.; Chin, J.; Ding, G. J.-F.; Egger, L. A.; Gaffney, E. P.; Limjuco, G.; Palyha, O. C.; Raju, S. M.; Roland, A. M.; Salley, J. P.; Yamin, T.-T.; Lee, J. A.; Shively, J. E.; Maccross, M.; Mumford, R. A.; Schmidt, J. A.; Tocci, M. J. Nature 1992, 356, 768.
4. (b) Gerretti, D. P.; Kozlosky, C. J.; Mosley, B.; Nelson, N.; Ness, K. V.; Greenstreet, T. A.; March, C. J.; Kronheim, S. R.; Druck, T.; Cannizzaro, L. A.; Huebner, K.; Black, R. A. Science 1992, 256, 97.
5. Ku, G.; Faust, T.; Lauffer, L. L.; Livingston, D. J.; Harding, M. W. Cytokine 1996, 8, 377.
6. (a) Koizumi, F.; Matsuda, Y.; Nakanishi, S. J. Antibiot. 2003, 56, 464.
7. (b) Koizumi, F.; Ishiguro, H.; Ando, K.; Kondo, H.; Yoshida, M.; Matsuda, Y.; Nakanishi, S. J. Antibiot. 2003, 56, 603.
8. Kakeya, H.; Miyake, Y.; Shoji, M.; Kishida, S.; Hayashi, Y.; Kataoka, T.; Osada, H. Bioorg. Med. Chem. Lett. 2003, 13, 3743.
9. Isolation: (a) Kakeya, H.; Onose, R.; Koshino, H.; Yoshida, A.; Kobayashi, K.; Kageyama, S.-I.; Osada, H. J. Am. Chem. Soc. 2002, 124, 3496.
10. (b) Kakeya, H.; Onose, R.; Yoshida, A.; Koshino, H.; Osada, H. J. Antibiot. 2002, 55, 829.
11. Total syntheses by our group, see: (c) Shoji, M.; Yamaguchi, J.; Kakeya, H.; Osada, H.; Hayashi, Y. Angew. Chem., Int. Ed. 2002, 41, 3192.
12. (d) Shoji, M.; Kishida, S.; Takeda, M.; Kakeya, H.; Osada, H.; Hayashi, Y. Tetrahedron Lett. 2002, 43, 9155.
13. (e) Shoji, M.; Kishida, S.; Kodera, Y.; Shiina, I.; Kakeya, H.; Osada, H.; Hayashi, Y. Tetrahedron Lett. 2003, 44, 7205.
14. (f) Shoji, M.; Imai, H.; Shiina, I.; Kakeya, H.; Osada, H.; Hayashi, Y. J. Org. Chem. 2004, 69, 1548.
15. (g) Shoji, M.; Imai, H.; Mukaida, M.; Sakai, K.; Kakeya, H.; Osada, H.; Hayashi, Y. J. Org. Chem. 2005, 70, 79.
16. Other groups' total syntheses, see: (h) Li, C.; Bardhan, S.; Pace, E. A.; Liang, M.-C.; Gilmore, T. D.; Porco, J. A., Jr. Org. Lett. 2002, 4, 3267.
17. (i) Mehta, G.; Islam, K.; Tetrahedron Lett. 2003, 44, 3569.
18. (j) Mehta, G.; Islam, K. Tetrahedron Lett. 2004, 45, 3611.
19. (k) Kuwahara, S.; Imada, S. Tetrahedron Lett. 2005, 46, 547.
20. (l) Li, C.; Porco, J. A., Jr. J. Org. Chem. 2005, 70, 6053.
21. (a) Epiepoformin: Nagasawa, H.; Suzuki, A.; Tamura, S. Agric. Biol. Chem. 1978, 42, 1303.
22. (b) Epiepoxydon: Ichihara, A.; Kimura, R.; Oda, K.; Koichi, M.; Sakamura, S. Tetrahedron Lett. 1976, 4741.
23. Nagasawa, H.; Suzuki, A.; Tamura, S. Agric. Biol. Chem. 1978, 42, 1303.
24. Sekiguchi, J.; Gaucher, G. M. Biochem. J. 1979, 182, 445.
25. (c) Harveynone: Nagata, T.; Ando, Y.; Hirota, A. Biosci. Biotechnol. Biochem,. 1992, 56, 810.
26. Kawazu, K.; Kobayashi, A.; Oe, K. JP 03041075, 1991; Chem. Abstr. 1991, 115, 181517.
27. (d) Tricholomenyn A: Garlaschelli, L.; Magistrali, E.; Vidari, G.; Zuffardi, O. Tetrahedron Lett. 1995, 36, 5633.
28. (e) Panepoxydon, Isopanepoxydon: Kis, Z.; Glosse, A.; Sigg, H. P.; Hruban, L.; Snatzke, G. Helv. Chim. Acta 1970, 53, 1577.
29. Erkel, G.; Anke, T.; Sterner, O. Biochem. Biophys. Res. Commun. 1996, 226, 214.
30. (f) Cycloepoxydon: Gehrt, A.; Erkel, G.; Anke, T.; Sterner, O. J. Antibiot. 1998, 51, 455.
31. Gehrt, A.; Erkel, G.; Anke, H.; Anke, T.; Sterner, O. Nat. Prod. Lett. 1997, 9, 259.
32. (g) Terremutin: Miller, M. W. Tetrahedron 1968, 24, 4839.
33. Read, G.; Ruiz, V. M. J. Chem. Soc. C 1970, 1945.
34. (h) Bromoxone: Higa, T.; Okuda, R. K.; Severns, R. M.; Scheuer, P. J.; He, C.-H.; Changfu, X.; Clardy, J. Tetrahedron 1987, 43, 1063.
35. (i) Chaloxone: Fex, T.; Trofast, J.; Wickberg, B. Acta Chem. Scand. B 1981, 35, 91.
36. Fex, T.; Wickberg, B. Acta Chem. Scand. B 1981, 35, 97.
37. Grewe, R.; Kersten, S. Chem. Ber. 1967, 100, 2546.
38. (j) Jesterone: Li, J. Y.; Strobel, G. A. Phytochemistry 2001, 57, 261.
39. (k) Epoxyquinomycin C, D: Matsumoto, N.; Tuchida, T.; Umekita, M.; Kinoshita, N.; Iinuma, H.; Sawa, T.; Hamada, M.; Takeuchi, T. J. Antibiot. 1997, 50, 900.
40. Matsumoto, N.; Tuchida, T.; Sawa, R.; Iinuma, H.; Nakamura, H.; Naganawa, H.; Sawa, T.; Takeuchi, T. J. Antibiot. 1997, 50, 912.
41. For reviews, see: Marco-Contelles, J.; Molina, M. T.; Anjum, S. Chem. Rev. 2004, 104, 2857.
42. Koizumi, F.; Takahashi, Y.; Ishiguro, H.; Tanaka, R.; Ohtaki, S.; Yoshida, M.; Nakanishi, S.; Ikeda, S. Tetrahedron Lett. 2004, 45, 7419.
43. Shoji, M.; Uno, T.; Hayashi, Y. Org. Lett. 2004, 6, 4535.
44. Marvell, E. N. Thermal Electrocyclic Reactions; Academic Press: New York, 1980.
45. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4370.
46. Ruel, F. S.; Braun, M. P.; Johnson, C. R. Org. Synth. 1997, 75, 69.
47. Rodriguez-Otero, J. J. Org. Chem. 1999, 64, 6842.
48. TITAN 1.0.5. Schrodinger, Inc.: Irvine, CA, and Wavefunction, Inc.: Portland, OR, 2000. http://www.schrodinger.com; http:// www.wavefun.com.
49. (a) Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175.
50. (b) Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
51. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139.
52. (a) Nishizawa, M.; Takenaka, H.; Nishida, H.; Hayashi, Y. Tetrahedron Lett. 1983, 24, 2581.
53. (b) Nishizawa, M.; Morikuni, E.; Asoh, K.; Kan, Y.; Uenoyama, K.; Imagawa, H. Synlett 1995, 169.
54. (c) Imagawa, H.; Shigaraki, T.; Suzuki, T.; Takao, T.; Yamada, H.; Sugihara, T.; Nishizawa, M. Chem. Pharm. Bull. 1998, 46, 1341.
55. (d) Nishizawa, M.; Kashima, T.; Sakakibara, M.; Wakabayashi, A.; Takahashi, K.; Takao, T.; Imagawa, H.; Sugihara, T. Heterocycles 2000, 54, 629.
56. (a) Korte, D. E.; Hegedus, L. S.; Wirth, R. K. J. Org. Chem. 1977, 42, 1329.
57. (b) Minami, T.; Nishimoto, A.; Hanaoka, M. Tetrahedron Lett. 1995, 36, 9505.
58. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
59. The reason for the effect of the concentration on the diastereoselectivity is not clear.
60. Whitesides, G. M.; San Filippo, J., Jr. J. Am. Chem. Soc. 1970, 92, 6611.
61. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; John Wiley and Sons: New York, 1967; Vol. 1, p 1276.
62. Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 2596.