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Volumn 15, Issue 39, 2009, Pages 10144-10157

Epothilone analogues with benzimidazole and quinoline side chains: Chemical synthesis, antiproliferative activity, and interactions with tubulin

Author keywords

Antitumor agents epothilone; Microtubules natural products; Structure activity relationships; Total synthesis

Indexed keywords

ANTIPROLIFERATIVE ACTIVITIES; ANTITUMOR AGENTS EPOTHILONE; BENZIMIDAZOLES; CHEMICAL SYNTHESIS; EPOTHILONES; FUNCTIONALIZED; HUMAN CANCER CELLS; IN-VITRO; MICROTUBULES; MICROTUBULES NATURAL PRODUCTS; POTENT INHIBITION; PRODRUGS; SIDE CHAINS; STRUCTURE-ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS; TUBULIN POLYMERIZATION;

EID: 70349689996     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901376     Document Type: Article
Times cited : (28)

References (71)
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    • It should be noted that we have not rigorously established the configuration of 10, as we were unable to obtain crystals suitable for X-ray crystallographic analysis. However, the preferred stereochemical outcome of acetate aldol reactions with Oppolzer sultam 8 is well established (see, for example, refs. [27,28]). In addition, we have been able to unambiguously determine the configuration of the major aldol product obtained from 8 and an aldehyde closely related to 7 as S (unpublished results). In the light of these facts, it is safe to assume that 10 has the desired S configuration.
    • It should be noted that we have not rigorously established the configuration of 10, as we were unable to obtain crystals suitable for X-ray crystallographic analysis. However, the preferred stereochemical outcome of acetate aldol reactions with Oppolzer sultam 8 is well established (see, for example, refs. [27,28]). In addition, we have been able to unambiguously determine the configuration of the major aldol product obtained from 8 and an aldehyde closely related to 7 as S (unpublished results). In the light of these facts, it is safe to assume that 10 has the desired S configuration.
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    • The ee of the allylation product 25 was determined by Mosher ester analysis to be 94 %. The optical rotation of the TBS-analogue of aldehyde 27 (obtained from 25 through TBS-protection and ozonolysis) matched that of material prepared by the Oppolzer sultam approach (unpublished data).
    • The ee of the allylation product 25 was determined by Mosher ester analysis to be 94 %. The optical rotation of the TBS-analogue of aldehyde 27 (obtained from 25 through TBS-protection and ozonolysis) matched that of material prepared by the Oppolzer sultam approach (unpublished data).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.