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Volumn 4, Issue 22, 2002, Pages 3815-3818

SAR and pH Stability of Cyano-Substituted Epothilones

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; EPOTHILONE DERIVATIVE; TUBULIN;

EID: 0001620405     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026589j     Document Type: Article
Times cited : (39)

References (31)
  • 11
    • 0442263682 scopus 로고    scopus 로고
    • For instance, tubulin affinity is completely lost with the C-15 epimer, the C-6 epimer, and the C-8 epimer (ref 3a)
    • For instance, tubulin affinity is completely lost with the C-15 epimer, the C-6 epimer, and the C-8 epimer (ref 3a).
  • 17
    • 0442263678 scopus 로고    scopus 로고
    • The synthesis of 7 and 8 was first disclosed by Höfle and co-workers in patent literature (DE 19639456.2)
    • The synthesis of 7 and 8 was first disclosed by Höfle and co-workers in patent literature (DE 19639456.2).
  • 18
    • 0442266807 scopus 로고    scopus 로고
    • note
    • The NOE pattern between epothilone A and B analogues with the same relative stereochemistry was remarkably similar. NOE effects between H-3 and H-6, H-3 and H-8, as well as H-3 and the adjacent methyl with a lower chemical shift could be observed for all (3S)-diastereoisomers.
  • 19
    • 0442268285 scopus 로고    scopus 로고
    • note
    • w = 0.065 for 1256 observed intensities (I > 3σ(I)), mp = 158-161 °C. Only one position is shown for some rotamerically disordered ethyls of the triethylsilyl group of 11. Crystallographic data (excluding structure factors) for the above compounds have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-190177, -190176. and -190178, respectively. Copies of the data can be obtained free of charge upon application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: (+44)1223-336-033. E-mail: deposit@ ccdc.cam.ac.uk).
  • 21
    • 0442265223 scopus 로고    scopus 로고
    • 95 refers to 5% degradation of compound in pH 1 buffer as determined by HPLC analysis
    • 95 refers to 5% degradation of compound in pH 1 buffer as determined by HPLC analysis.
  • 30
    • 0442268284 scopus 로고    scopus 로고
    • The improved pH stability may be due to the presence of the nitrile group as we anticipated, although the altered epoxide geometry of 24 cannot be ruled out
    • The improved pH stability may be due to the presence of the nitrile group as we anticipated, although the altered epoxide geometry of 24 cannot be ruled out.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.