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Volumn 3, Issue 17, 2001, Pages 2693-2696

Synthesis and biological activity of novel epothilone aziridines

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; AZIRIDINE DERIVATIVE; EPOXIDE;

EID: 0035940099     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016273w     Document Type: Article
Times cited : (77)

References (36)
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    • (g) Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. Engl. 1998, 37, 2014; Angew. Chem. 1998 110, 2120.
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    • Epothilones A and B: Springboards for the synthesis of promising antimitotic agents
    • Abstracts of Papers, San Francisco, CA, March 26-30, 2000; American Chemical Society: Washington, DC
    • For a preliminary account of the work described herein and additional studies on the epothilones, see: (a) Vite, G.; Borzilleri, R.; Fooks, C.; Johnson, J. A.; Kim, S.-H.; Leavitt, K.; Mitt, T.; Regueiro-Ren, A.; Schmidt, R.; Zheng, P.; Lee F. Epothilones A and B: Springboards for the synthesis of promising antimitotic agents. In Abstracts of Papers, 219th National Meeting of the American Chemical Society, San Francisco, CA, March 26-30, 2000; American Chemical Society: Washington, DC, 2000; no. 286.
    • (2000) 219th National Meeting of the American Chemical Society , vol.286
    • Vite, G.1    Borzilleri, R.2    Fooks, C.3    Johnson, J.A.4    Kim, S.-H.5    Leavitt, K.6    Mitt, T.7    Regueiro-Ren, A.8    Schmidt, R.9    Zheng, P.10    Lee, F.11
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    • (b) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langride-Smith, P. R. R.; Millar, J. R. A.; Taylor, A. T. Tetrahedron Lett. 1994, 35, 9067. Seno, M.; Namba, T.; Kise, H. J. Org. Chem. 1978, 43, 3345.
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    • note
    • 2Cb, MeOH); and alternative dioxirane source (trifluoroacetone) had no effect on the diastereoselectivity. Other oxidation methods, such as m-CPBA and DMDO, generated the N-oxide and/or the C16-C17 epoxide as side products.
  • 30
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    • note
    • +.
  • 31
    • 0042797297 scopus 로고    scopus 로고
    • note
    • Higher reaction temperatures afforded a 1:1 ratio of the bromohydrins along with other side products.
  • 33
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    • note
    • Aziridine 11 could also be prepared directly from azido alcohol 10 by reduction and in situ ring closure with trimethylphosphine, but only in 30% yield.
  • 35
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    • 0.01 values are expressed as the mean with standard deviation obtained from three different concentrations, (b) Cytoxicity was assessed in HCT-116 human colon carcinoma cells by MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-car-boxymethoxyphenyl)-2-(4-sulphenyl)-2H- tetrazolium, inner salt) assay as reported in Riss, T. L.; Moravec, R. A. Mol. Biol. Cell 1992, 3(Suppl), 184a (abstract 1067).
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    • abstract 1067
    • 0.01 values are expressed as the mean with standard deviation obtained from three different concentrations, (b) Cytoxicity was assessed in HCT-116 human colon carcinoma cells by MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-car-boxymethoxyphenyl)-2-(4-sulphenyl)-2H- tetrazolium, inner salt) assay as reported in Riss, T. L.; Moravec, R. A. Mol. Biol. Cell 1992, 3(Suppl), 184a (abstract 1067).
    • (1992) Mol. Biol. Cell , vol.3 , Issue.SUPPL.
    • Riss, T.L.1    Moravec, R.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.