A synthesis of the derivatives of 1,2,3,5,10,10a-hexahydrobenz[f]indolizine-6,9-dione having antifungal activity as a simple model of saframycin A

Heterocycles

Volumn 42, Issue 1, 1996, Pages 195-211

  Kubo, Akinori ^a   Nakai, Tatsuya ^a   Koizumi, Yuichi ^a   Kitahara, Yoshiyasu ^a   Saito, Naoki ^a   Mikami, Yuzuru ^b   Yazawa, Katsukiyo ^b   Uno, Jun ^b  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001443159     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-94-S5-1     Document Type: Article

References (30)

1. A. Kubo, T. Nakai, Y. Koizumi, N. Saito, Y. Mikami, K. Yazawa, and J. Uno, Heterocycles, 1992, 34, 1201.
2. A. Kubo and N. Saito, 'Studies in Natural Products Chemistry', ed. by Atta-Ur-Rahman, Elsevier, Inc., Amsterdam, 1992, Vol. 10, pp. 77-145.
3. Cyanocycline A see: T. Hayashi, T. Noto, Y. Nawata, H. Okazaki, M. Sawada, and K. Ando, J. Antibiot., 1982, 35, 771; T. Hayashi and Y. Nawata, J. Chem. Soc., Perkin Trans. 2, 1983, 335: DX-52-1 see: H. Saito and T. Hirata, Tetrahedron Lett., 1987, 28, 4065; H. Saito, S. Kobayashi, Y. Uosaki, A. Sato, K. Fujimoto, K. Miyoshi, T. Ashizawa, M. Morimoto, and T. Hirata, Chem. Pharm. Bull., 1990, 38, 1278.
4. Cyanocycline A see: T. Hayashi, T. Noto, Y. Nawata, H. Okazaki, M. Sawada, and K. Ando, J. Antibiot., 1982, 35, 771; T. Hayashi and Y. Nawata, J. Chem. Soc., Perkin Trans. 2, 1983, 335: DX-52-1 see: H. Saito and T. Hirata, Tetrahedron Lett., 1987, 28, 4065; H. Saito, S. Kobayashi, Y. Uosaki, A. Sato, K. Fujimoto, K. Miyoshi, T. Ashizawa, M. Morimoto, and T. Hirata, Chem. Pharm. Bull., 1990, 38, 1278.
5. Cyanocycline A see: T. Hayashi, T. Noto, Y. Nawata, H. Okazaki, M. Sawada, and K. Ando, J. Antibiot., 1982, 35, 771; T. Hayashi and Y. Nawata, J. Chem. Soc., Perkin Trans. 2, 1983, 335: DX-52-1 see: H. Saito and T. Hirata, Tetrahedron Lett., 1987, 28, 4065; H. Saito, S. Kobayashi, Y. Uosaki, A. Sato, K. Fujimoto, K. Miyoshi, T. Ashizawa, M. Morimoto, and T. Hirata, Chem. Pharm. Bull., 1990, 38, 1278.
6. Cyanocycline A see: T. Hayashi, T. Noto, Y. Nawata, H. Okazaki, M. Sawada, and K. Ando, J. Antibiot., 1982, 35, 771; T. Hayashi and Y. Nawata, J. Chem. Soc., Perkin Trans. 2, 1983, 335: DX-52-1 see: H. Saito and T. Hirata, Tetrahedron Lett., 1987, 28, 4065; H. Saito, S. Kobayashi, Y. Uosaki, A. Sato, K. Fujimoto, K. Miyoshi, T. Ashizawa, M. Morimoto, and T. Hirata, Chem. Pharm. Bull., 1990, 38, 1278.
7. Saframycin A see: K. Ishiguro, K. Takahashi, K. Yazawa, S. Sakiyama, and T. Arai, J. Biol. Chem., 1981, 256, 2162; J. W. Lown, A. V. Joshua, and J. S. Lee, Biochemistry, 1982, 21, 419; G. C. Hill and W. A. Remers, J. Med Chem., 1991, 34, 1990: Cyanocycline A see: M. B. Cox, P. Arjunan, and S. K. Arora, J. Antibiot., 1991, 44, 885: DX-52-1 see: K. Fujimoto, T. Oka, and M. Morimoto, Cancer Res., 1987, 47, 1516; S. Inaba and M. Shimoyama, ibid., 1988, 48, 6029; G. C. Hill, T. R. Wunz, and W. A. Remers, J. Comput. -Aided Mol. Des., 1988, 2, 91; R. M. Williams, T. Glinka, M. E. Flanagan, R. Gallegos, H. Coffman, and D. Pei, J. Am. Chem. Soc., 1992, 114, 733.
8. Saframycin A see: K. Ishiguro, K. Takahashi, K. Yazawa, S. Sakiyama, and T. Arai, J. Biol. Chem., 1981, 256, 2162; J. W. Lown, A. V. Joshua, and J. S. Lee, Biochemistry, 1982, 21, 419; G. C. Hill and W. A. Remers, J. Med Chem., 1991, 34, 1990: Cyanocycline A see: M. B. Cox, P. Arjunan, and S. K. Arora, J. Antibiot., 1991, 44, 885: DX-52-1 see: K. Fujimoto, T. Oka, and M. Morimoto, Cancer Res., 1987, 47, 1516; S. Inaba and M. Shimoyama, ibid., 1988, 48, 6029; G. C. Hill, T. R. Wunz, and W. A. Remers, J. Comput. -Aided Mol. Des., 1988, 2, 91; R. M. Williams, T. Glinka, M. E. Flanagan, R. Gallegos, H. Coffman, and D. Pei, J. Am. Chem. Soc., 1992, 114, 733.
9. Saframycin A see: K. Ishiguro, K. Takahashi, K. Yazawa, S. Sakiyama, and T. Arai, J. Biol. Chem., 1981, 256, 2162; J. W. Lown, A. V. Joshua, and J. S. Lee, Biochemistry, 1982, 21, 419; G. C. Hill and W. A. Remers, J. Med Chem., 1991, 34, 1990: Cyanocycline A see: M. B. Cox, P. Arjunan, and S. K. Arora, J. Antibiot., 1991, 44, 885: DX-52-1 see: K. Fujimoto, T. Oka, and M. Morimoto, Cancer Res., 1987, 47, 1516; S. Inaba and M. Shimoyama, ibid., 1988, 48, 6029; G. C. Hill, T. R. Wunz, and W. A. Remers, J. Comput. -Aided Mol. Des., 1988, 2, 91; R. M. Williams, T. Glinka, M. E. Flanagan, R. Gallegos, H. Coffman, and D. Pei, J. Am. Chem. Soc., 1992, 114, 733.
10. Saframycin A see: K. Ishiguro, K. Takahashi, K. Yazawa, S. Sakiyama, and T. Arai, J. Biol. Chem., 1981, 256, 2162; J. W. Lown, A. V. Joshua, and J. S. Lee, Biochemistry, 1982, 21, 419; G. C. Hill and W. A. Remers, J. Med Chem., 1991, 34, 1990: Cyanocycline A see: M. B. Cox, P. Arjunan, and S. K. Arora, J. Antibiot., 1991, 44, 885: DX-52-1 see: K. Fujimoto, T. Oka, and M. Morimoto, Cancer Res., 1987, 47, 1516; S. Inaba and M. Shimoyama, ibid., 1988, 48, 6029; G. C. Hill, T. R. Wunz, and W. A. Remers, J. Comput. -Aided Mol. Des., 1988, 2, 91; R. M. Williams, T. Glinka, M. E. Flanagan, R. Gallegos, H. Coffman, and D. Pei, J. Am. Chem. Soc., 1992, 114, 733.
11. Saframycin A see: K. Ishiguro, K. Takahashi, K. Yazawa, S. Sakiyama, and T. Arai, J. Biol. Chem., 1981, 256, 2162; J. W. Lown, A. V. Joshua, and J. S. Lee, Biochemistry, 1982, 21, 419; G. C. Hill and W. A. Remers, J. Med Chem., 1991, 34, 1990: Cyanocycline A see: M. B. Cox, P. Arjunan, and S. K. Arora, J. Antibiot., 1991, 44, 885: DX-52-1 see: K. Fujimoto, T. Oka, and M. Morimoto, Cancer Res., 1987, 47, 1516; S. Inaba and M. Shimoyama, ibid., 1988, 48, 6029; G. C. Hill, T. R. Wunz, and W. A. Remers, J. Comput. -Aided Mol. Des., 1988, 2, 91; R. M. Williams, T. Glinka, M. E. Flanagan, R. Gallegos, H. Coffman, and D. Pei, J. Am. Chem. Soc., 1992, 114, 733.
12. Saframycin A see: K. Ishiguro, K. Takahashi, K. Yazawa, S. Sakiyama, and T. Arai, J. Biol. Chem., 1981, 256, 2162; J. W. Lown, A. V. Joshua, and J. S. Lee, Biochemistry, 1982, 21, 419; G. C. Hill and W. A. Remers, J. Med Chem., 1991, 34, 1990: Cyanocycline A see: M. B. Cox, P. Arjunan, and S. K. Arora, J. Antibiot., 1991, 44, 885: DX-52-1 see: K. Fujimoto, T. Oka, and M. Morimoto, Cancer Res., 1987, 47, 1516; S. Inaba and M. Shimoyama, ibid., 1988, 48, 6029; G. C. Hill, T. R. Wunz, and W. A. Remers, J. Comput. -Aided Mol. Des., 1988, 2, 91; R. M. Williams, T. Glinka, M. E. Flanagan, R. Gallegos, H. Coffman, and D. Pei, J. Am. Chem. Soc., 1992, 114, 733.
13. Saframycin A see: K. Ishiguro, K. Takahashi, K. Yazawa, S. Sakiyama, and T. Arai, J. Biol. Chem., 1981, 256, 2162; J. W. Lown, A. V. Joshua, and J. S. Lee, Biochemistry, 1982, 21, 419; G. C. Hill and W. A. Remers, J. Med Chem., 1991, 34, 1990: Cyanocycline A see: M. B. Cox, P. Arjunan, and S. K. Arora, J. Antibiot., 1991, 44, 885: DX-52-1 see: K. Fujimoto, T. Oka, and M. Morimoto, Cancer Res., 1987, 47, 1516; S. Inaba and M. Shimoyama, ibid., 1988, 48, 6029; G. C. Hill, T. R. Wunz, and W. A. Remers, J. Comput. -Aided Mol. Des., 1988, 2, 91; R. M. Williams, T. Glinka, M. E. Flanagan, R. Gallegos, H. Coffman, and D. Pei, J. Am. Chem. Soc., 1992, 114, 733.
14. Saframycin A see: K. Ishiguro, K. Takahashi, K. Yazawa, S. Sakiyama, and T. Arai, J. Biol. Chem., 1981, 256, 2162; J. W. Lown, A. V. Joshua, and J. S. Lee, Biochemistry, 1982, 21, 419; G. C. Hill and W. A. Remers, J. Med Chem., 1991, 34, 1990: Cyanocycline A see: M. B. Cox, P. Arjunan, and S. K. Arora, J. Antibiot., 1991, 44, 885: DX-52-1 see: K. Fujimoto, T. Oka, and M. Morimoto, Cancer Res., 1987, 47, 1516; S. Inaba and M. Shimoyama, ibid., 1988, 48, 6029; G. C. Hill, T. R. Wunz, and W. A. Remers, J. Comput. -Aided Mol. Des., 1988, 2, 91; R. M. Williams, T. Glinka, M. E. Flanagan, R. Gallegos, H. Coffman, and D. Pei, J. Am. Chem. Soc., 1992, 114, 733.
15. Compound (5): S. Saito, K. Tanaka, K. Nakatani, F. Matsuda, T. Katoh, S. Terashima, Tetrahedron, 1994, 50, 6209; T. Katoh, M. Kirihara, T. Yoshino, O. Tamura, F. Ikeuchi, K. Nakatani, F. Matsuda, K. Yamada, K. Gomi, T. Ashizawa, and S. Terashima, ibid., 1994, 50, 6259; T. Katoh and S. Terashima, J. Synth. Org. Chem. Jpn., 1994, 52, 556: Compound 6: R. M. Williams, T. Glinka, R. Gallegos, P. P. Ehrlich, M. E. Flanagan, H. Coffman, and G. Park, Tetrahedron, 1991, 47, 2629.
16. Compound (5): S. Saito, K. Tanaka, K. Nakatani, F. Matsuda, T. Katoh, S. Terashima, Tetrahedron, 1994, 50, 6209; T. Katoh, M. Kirihara, T. Yoshino, O. Tamura, F. Ikeuchi, K. Nakatani, F. Matsuda, K. Yamada, K. Gomi, T. Ashizawa, and S. Terashima, ibid., 1994, 50, 6259; T. Katoh and S. Terashima, J. Synth. Org. Chem. Jpn., 1994, 52, 556: Compound 6: R. M. Williams, T. Glinka, R. Gallegos, P. P. Ehrlich, M. E. Flanagan, H. Coffman, and G. Park, Tetrahedron, 1991, 47, 2629.
17. Compound (5): S. Saito, K. Tanaka, K. Nakatani, F. Matsuda, T. Katoh, S. Terashima, Tetrahedron, 1994, 50, 6209; T. Katoh, M. Kirihara, T. Yoshino, O. Tamura, F. Ikeuchi, K. Nakatani, F. Matsuda, K. Yamada, K. Gomi, T. Ashizawa, and S. Terashima, ibid., 1994, 50, 6259; T. Katoh and S. Terashima, J. Synth. Org. Chem. Jpn., 1994, 52, 556: Compound 6: R. M. Williams, T. Glinka, R. Gallegos, P. P. Ehrlich, M. E. Flanagan, H. Coffman, and G. Park, Tetrahedron, 1991, 47, 2629.
18. Compound (5): S. Saito, K. Tanaka, K. Nakatani, F. Matsuda, T. Katoh, S. Terashima, Tetrahedron, 1994, 50, 6209; T. Katoh, M. Kirihara, T. Yoshino, O. Tamura, F. Ikeuchi, K. Nakatani, F. Matsuda, K. Yamada, K. Gomi, T. Ashizawa, and S. Terashima, ibid., 1994, 50, 6259; T. Katoh and S. Terashima, J. Synth. Org. Chem. Jpn., 1994, 52, 556: Compound 6: R. M. Williams, T. Glinka, R. Gallegos, P. P. Ehrlich, M. E. Flanagan, H. Coffman, and G. Park, Tetrahedron, 1991, 47, 2629.
19. T. F. Buckley III and H. Rapoport, I. Org. Chem., 1983, 48, 4222.
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21. B. Rigo and N. Kolocouris, J. Heterocycl. Chem., 1983, 20, 893; L. L. Martin, S. J. Scott, M. N. Agnew, and L. L. Setescak, J. Org. Chem., 1986, 51, 3697; and see: B. Rigo, P. Gautret, A. Legrand, S. E. Ghammarti, and D. Couturier, Synth. Commun., 1994, 24, 2609.
22. B. Rigo and N. Kolocouris, J. Heterocycl. Chem., 1983, 20, 893; L. L. Martin, S. J. Scott, M. N. Agnew, and L. L. Setescak, J. Org. Chem., 1986, 51, 3697; and see: B. Rigo, P. Gautret, A. Legrand, S. E. Ghammarti, and D. Couturier, Synth. Commun., 1994, 24, 2609.
23. K. Matsuo, M. Okumura, and K. Tanaka, Chem. Pharm. Bull., 1982, 30, 4170; Y. Kitahara, S. Nakahara, R. Numata, and A. Kubo, ibid., 1985, 33, 2122.
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25. C. T. West, S. J. Donnelly, D. A. Kooistra, and M. P. Doyle, J. Org. Chem., 1973, 38, 2675; D. N. Kursanov, Z. N. Parnes, and N. M. Loim, Synthesis, 1974, 633.
26. C. T. West, S. J. Donnelly, D. A. Kooistra, and M. P. Doyle, J. Org. Chem., 1973, 38, 2675; D. N. Kursanov, Z. N. Parnes, and N. M. Loim, Synthesis, 1974, 633.
27. Hydrogenolysis of 16 using usual catalyst (absence or presence of acid) and reductive removal of a hydroxyl group with sodium borohydride in acetic acid were totally failed, only starting material was recovered. The replacement of a hydroxyl group of 16 to the corresponding halide and treatment of 16 with mesyl chloride or tosyl chloride in pyridine caused decomposition of the starting material.
28. P. Deslongchamps, 'Stereoelectronic Effects in Organic Chemistry', Pregamon Press, New York, 1983, Vol. 1, pp. 211-221.
29. As preliminary experiment, the oxidative demethylation of 16 employing cerium(IV) ammonium nitrate gave the quinone (29) in 52 % yield, and using argentic oxide in 39% yield (Y. Kitahara, S. Nakahara, Y. Koizumi, H. Muranishi, and A. Kubo, Chem. Pharm. Bull., 1988, 36, 3623).
30. MIC was determined by the agar (Difco) for fungi. In vitro activity of compounds (7 and 26) was determined from the size of inhibition zone using paper disk and T. mentagrophytes as test organism.