Revised structure of kasarin, an antibacterial pyrazinone compound from the marine microorganism Hyphomycetes sp.

Tetrahedron Letters

Volumn 48, Issue 49, 2007, Pages 8628-8631

  Kita, Masaki ^a   Miwa, Ryoka ^a   Widianti, Triana ^a   Ozaki, Yoshikazu ^a   Aoyama, Sachiko ^a   Yamada, Kaoru ^a   Uemura, Daisuke ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Antibacterial marine alkaloid; Kasarin; Pyrazinone; Spectroscopic analysis; Structural revision

Indexed keywords

5 MALONYLOXY 1 METHOXY PYRAZIN 2 ONE DERIVATIVE; ALKALOID; ANTIINFECTIVE AGENT; CARBON; KASARIN; LACTONE DERIVATIVE; OXAZOLONE; PYRAZINE DERIVATIVE; PYRAZINONE COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HYPHOMYCETES; INFRARED SPECTROSCOPY; MARINE BACTERIUM; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

HYPHOMYCETES;

EID: 35748931777     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.024     Document Type: Article

References (24)

1. Kita M., Kondo M., Koyama T., Yamada K., Matsumoto T., Lee K.-H., Woo J.-T., and Uemura D. J. Am. Chem. Soc. 126 (2004) 4794
2. Kita M., Ohishi N., Washida K., Kondo M., Koyama T., Yamada K., and Uemura D. Bioorg. Med. Chem. 13 (2005) 5253
3. Washida K., Koyama T., Yamada K., Kita M., and Uemura D. Tetrahedron Lett. 47 (2006) 2521
4. Kita M., Ohishi N., Konishi K., Kondo M., Koyama T., Kitamura M., Yamada K., and Uemura D. Tetrahedron 63 (2007) 6241
5. Kita M., Roy M.C., Siwu E.R.O., Noma I., Takiguchi T., Itoh M., Yamada K., Koyama T., Iwashita T., and Uemura D. Tetrahedron Lett. 48 (2007) 3423
6. Kita M., Roy M.C., Siwu E.R.O., Noma I., Takiguchi T., Yamada K., Koyama T., Iwashita T., Wakamiya A., and Uemura D. Tetrahedron Lett. 48 (2007) 3429
7. Suenaga K., Aoyama S., Xi W., Arimoto H., Yamaguchi K., Yamada K., Tsuji T., Yamada A., and Uemura D. Heterocycles 52 (2000) 1033
8. Kuramoto M., Hayashi K., Yamaguchi K., Yada M., Tsuji T., and Uemura D. Bull. Chem. Soc. Jpn. 71 (1998) 771
9. Kuramoto M., Hayashi K., Fujitani Y., Yamaguchi K., Tsuji T., Yamada K., Ijuin Y., and Uemura D. Tetrahedron Lett. 38 (1997) 5683
10. Fukuzawa S., Hayashi Y., Uemura D., Nagatsu A., Yamada K., and Ijyuin Y. Heterocycl. Commun. 1 (1995) 207
11. Recent reviews for bioactive nitrogenous marine metabolites:. Gerwick W.H., Tan L.T., and Sitachitta N. The Alkaloids 57 (2001) 75
12. Kuramoto M., Arimoto H., and Uemura D. Mar. Drugs 1 (2004) 39
13. Kita M., and Uemura D. Chem. Lett. 34 (2005) 454
14. Kita M., and Uemura D. In: Eguchi S. (Ed). Topics in Heterocycles Vol. 6 (2006), Springer 157-179
15. 3, 100 MHz) δ 168.0 (C3′), 166.0 (C1′), 161.5 (C3), 152.0 (C2), 135.0 (C6), 134.9 (C5), 64.1 (OMe), 41.1 (C2′), 33.7 (C7), 30.7 (C11), 27.5 (C8), 18.2 (C10), 12.6 (C9), 19.9 (C12), 19.9 (C13).
16. Ramtohul Y.K., Martin N.I., Silkin L., James M.N.G., and Vederas J.C. J. Chem. Soc., Perkin Trans. 1 (2002) 1351
17. Tone H., Matoba K., Goto F., Torisawa Y., Nishi T., and Minamikawa J. Org. Process Res. Dev. 4 (2000) 312
18. Shinhama K., Matoba K., Torisawa Y., and Minamikawa J. Tetrahedron 56 (2000) 7427
19. Kita Y., Akai S., Fujioka H., Tamura Y., Tone H., and Taniguchi Y. J. Chem. Soc., Perkin Trans. 1 (1994) 875
20. Kita Y., Akai S., Fujioka H., Tamura Y., Tone H., and Taniguchi Y. Tetrahedron Lett. 32 (1991) 6019
21. Thiolate-mediate cyclization of a valyl-isoleucyl dipeptide analog 11 was unsuccessful due to the steric repulsions of the side-chain methyl groups.{A figure is presented}.
22. Nakano Y., Kawaguchi T., Sumitomo J., Takizawa T., Uetsuki S., Sugawara M., and Kido M. J. Antibiot. 44 (1991) 52
23. 6, 175 MHz, based on HSQC and HMBC spectra) δ 176.2 (C6), 88.3 (C3), 63.9 (OMe), 35.7 (C11), 35.1 (C7), 27.2 (C8), 16.8 (C12), 16.5 (C10), 15.4 (C13), 11.7 (C9). Chemical shifts of the two carbonyl carbons (C2 and C5) could not be determined.
24. Compound 10 was isolated as a single stereoisomer, and its C3 epimer was not detected in the degraded products mixture.