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Volumn 77, Issue 10, 2004, Pages 1925-1930

The synthesis and biological activity of pyranonaphthoquione derivatives from Streptomyces sp. and their related substances

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; DERIVATIVES; ENZYME INHIBITION; ENZYMES; SYNTHESIS (CHEMICAL);

EID: 8444233646     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.77.1925     Document Type: Article
Times cited : (7)

References (32)
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    • Preliminary report see: a) A. Shimbashi, Y. Ishikawa, and S. Nishiyama, Tetrahedron Lett., 45, 939 (2004). b) M. Iinuma, T. Tanaka, and S. Matsuura, Chem. Pharm. Bull. 32, 2296 (1984).
    • (2004) Tetrahedron Lett. , vol.45 , pp. 939
    • Shimbashi, A.1    Ishikawa, Y.2    Nishiyama, S.3
  • 17
    • 85011238950 scopus 로고
    • Preliminary report see: a) A. Shimbashi, Y. Ishikawa, and S. Nishiyama, Tetrahedron Lett., 45, 939 (2004). b) M. Iinuma, T. Tanaka, and S. Matsuura, Chem. Pharm. Bull. 32, 2296 (1984).
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 2296
    • Iinuma, M.1    Tanaka, T.2    Matsuura, S.3
  • 18
    • 8444241384 scopus 로고    scopus 로고
    • note
    • 4.
  • 23
    • 33845551385 scopus 로고
    • 3 conditions, two alkyl substituents of the dihydropyran moiety adopt thermodynamically the more favorable trans-form than the corresponding cis-form. Examples of stability of the trans-form by thermodynamic control: a) M. F. Semmehak and A. Zask, J. Am. Chem. Soc., 105, 2034 (1983). b) A. D. Webb and T. M. Harris, Tetrahedron Lett., 18, 2069 (1977). c) T.-T. Li and R. H. Ellison, J. Am. Chem. Soc., 100, 6263 (1978). d) T. Masquelin, U. Hengartner, and J. Streith, Synthesis, 1995, 780.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2034
    • Semmehak, M.F.1    Zask, A.2
  • 24
    • 0017384705 scopus 로고
    • 3 conditions, two alkyl substituents of the dihydropyran moiety adopt thermodynamically the more favorable trans-form than the corresponding cis-form. Examples of stability of the trans-form by thermodynamic control: a) M. F. Semmehak and A. Zask, J. Am. Chem. Soc., 105, 2034 (1983). b) A. D. Webb and T. M. Harris, Tetrahedron Lett., 18, 2069 (1977). c) T.-T. Li and R. H. Ellison, J. Am. Chem. Soc., 100, 6263 (1978). d) T. Masquelin, U. Hengartner, and J. Streith, Synthesis, 1995, 780.
    • (1977) Tetrahedron Lett. , vol.18 , pp. 2069
    • Webb, A.D.1    Harris, T.M.2
  • 25
    • 0018070409 scopus 로고
    • 3 conditions, two alkyl substituents of the dihydropyran moiety adopt thermodynamically the more favorable trans-form than the corresponding cis-form. Examples of stability of the trans-form by thermodynamic control: a) M. F. Semmehak and A. Zask, J. Am. Chem. Soc., 105, 2034 (1983). b) A. D. Webb and T. M. Harris, Tetrahedron Lett., 18, 2069 (1977). c) T.-T. Li and R. H. Ellison, J. Am. Chem. Soc., 100, 6263 (1978). d) T. Masquelin, U. Hengartner, and J. Streith, Synthesis, 1995, 780.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 6263
    • Li, T.-T.1    Ellison, R.H.2
  • 26
    • 8444245094 scopus 로고    scopus 로고
    • 3 conditions, two alkyl substituents of the dihydropyran moiety adopt thermodynamically the more favorable trans-form than the corresponding cis-form. Examples of stability of the trans-form by thermodynamic control: a) M. F. Semmehak and A. Zask, J. Am. Chem. Soc., 105, 2034 (1983). b) A. D. Webb and T. M. Harris, Tetrahedron Lett., 18, 2069 (1977). c) T.-T. Li and R. H. Ellison, J. Am. Chem. Soc., 100, 6263 (1978). d) T. Masquelin, U. Hengartner, and J. Streith, Synthesis, 1995, 780.
    • Synthesis , vol.1995 , pp. 780
    • Masquelin, T.1    Hengartner, U.2    Streith, J.3
  • 28
    • 8444251256 scopus 로고    scopus 로고
    • note
    • b) The cis- and trans-isomers were formed in a ratio of ca. 1:3. The diastereomeric mixture was inseparable.
  • 29
    • 8444246613 scopus 로고    scopus 로고
    • note
    • Because the diastereomeric mixture was inseparable, crude 14 was used for Cdc25A phosphatase inhibition assay.
  • 30
    • 8444253190 scopus 로고    scopus 로고
    • note
    • 2, changed to ca. 4:1 by KOH, which might induce isomerization through successive β-elimination and Michael addition reactions.
  • 31
    • 8444224127 scopus 로고    scopus 로고
    • note
    • 4OAc-MeCN - 3/2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.