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Volumn 70, Issue 16, 2005, Pages 6196-6203

New cytotoxic salinosporamides from the marine actinomycete Salinispora tropica

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; ENZYME INHIBITION; METABOLITES; NITROGEN COMPOUNDS;

EID: 23044479278     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050511+     Document Type: Article
Times cited : (178)

References (55)
  • 3
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    • Goodfellow, M., Williams, S. T., Mordarski, M.; Academic Press: New York
    • Okami, Y.; Hotta, K. In Actinomycetes in Biotechnology; Goodfellow, M., Williams, S. T., Mordarski, M.; Academic Press: New York, 1988; pp 33-67.
    • (1988) Actinomycetes in Biotechnology , pp. 33-67
    • Okami, Y.1    Hotta, K.2
  • 36
    • 33544461357 scopus 로고    scopus 로고
    • Georg Thieme Publishers: Stuttgart, Germany
    • Jacque, J.; Gros, C.; Mourcier, S. Absolute Configurations of 6000 Selected Compounds with One Asymmetric Carbon Atom; Georg Thieme Publishers: Stuttgart, Germany, 1997. Specifically, see references for data on 1-chloro-4-methylhex-1-en-3-one, 1-chloro-4-methylhexane, 1-chloro-5- methylheptane, 1-bromo-3-methylnonane, 1-bromo-4-methylnonane, and the corresponding deshalogenated compounds.
    • (1997) Absolute Configurations of 6000 Selected Compounds with One Asymmetric Carbon Atom
    • Jacque, J.1    Gros, C.2    Mourcier, S.3
  • 37
    • 33544469640 scopus 로고    scopus 로고
    • note
    • 4 reduction in i-PrOH and also in DMSO. An attempt was also made to convert 1 to the iodo derivative using the Finkelstein reaction (NaI in refluxing acetone), which under these conditions was not successful.
  • 38
    • 2742535506 scopus 로고    scopus 로고
    • 8 where the structure was originally disclosed. During the review process on this manuscript, it was brought to our attention that the original figure was in violation of the IUPAC rules because a hashed line between two adjacent stereocenters (C-4 and C-5) is not allowed under this system. The stereochemical representations used in this paper for 1-9 are in accord with these IUPAC recommendations. See: Moss, G. P. Pure Appl. Chem. 1996, 68, 2193-2222.
    • (1996) Pure Appl. Chem. , vol.68 , pp. 2193-2222
    • Moss, G.P.1
  • 43
    • 33544462207 scopus 로고    scopus 로고
    • note
    • Attempts to determine the absolute configuration of C-5 in 8 and 9 by preparation of the MTPA derivatives resulted in elimination to form 7.
  • 44
    • 0023637841 scopus 로고
    • For an example of decarboxylation of a β-amide ester under basic conditions, see: Shehata, I. A.; Glennon, R. A. J. Heterocycl. Chem. 1987, 24, 1291-1295.
    • (1987) J. Heterocycl. Chem. , vol.24 , pp. 1291-1295
    • Shehata, I.A.1    Glennon, R.A.2
  • 45
    • 33544469532 scopus 로고    scopus 로고
    • note
    • Molecular modeling of the four potential diastereomers (4R,5R,6S; 4R,5S,6S; 4S,4R,6S; 4R,5R,6S) indicates that the lowest energy conformers of these diastereomers are all within 2 kcal/mol. This suggests that all four diastereomers should be produced, albeit in unequal amounts.
  • 51
    • 33544463643 scopus 로고    scopus 로고
    • note
    • Concentration that limited the growth of a cell line to 50% of the untreated control growth.
  • 52
    • 33544456113 scopus 로고    scopus 로고
    • note
    • Concentration that killed 50% of the treated cell line as compared to the untreated cells.
  • 55
    • 33544467774 scopus 로고    scopus 로고
    • note
    • Upper limit on the antibacterial, antifungal, and antiviral assays is 250, 500, and 20 μg/mL, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.