TY - JOUR
T1 - Heteroaromatic Taxol Analogues
T2 - The Chemistry and Biological Activities of 3′-Furyl and 3′-Pyridyl Substituted Taxanes
AU - Georg, Gunda I.
AU - Harriman, Gerlandine C B
AU - Hepperle, Michael
AU - Himes, Richard H.
PY - 1994/6/9
Y1 - 1994/6/9
N2 - A series of novel heterocyclic taxol analogues has been synthesized utilizing 2-azetidinones derived from the ester enolate-imine cyclocondensation. 2-Azetidinones possessing stereochemistry complementary to that of taxol's phenylisoserine side chain were synthesized in fair to high enantiomeric purity utilizing the chiral glycolate derived from Oppolzer's chiral auxiliary and the appropriate N-trimethylsilylaldimines. These novel analogues were evaluated in the microtubule assembly assay as well as tested for cytotoxicity against B16 melanoma cells. The 2-furyl analoug e29 proved to be more active than the parent, taxol.
AB - A series of novel heterocyclic taxol analogues has been synthesized utilizing 2-azetidinones derived from the ester enolate-imine cyclocondensation. 2-Azetidinones possessing stereochemistry complementary to that of taxol's phenylisoserine side chain were synthesized in fair to high enantiomeric purity utilizing the chiral glycolate derived from Oppolzer's chiral auxiliary and the appropriate N-trimethylsilylaldimines. These novel analogues were evaluated in the microtubule assembly assay as well as tested for cytotoxicity against B16 melanoma cells. The 2-furyl analoug e29 proved to be more active than the parent, taxol.
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U2 - 10.1016/S0960-894X(01)80366-8
DO - 10.1016/S0960-894X(01)80366-8
M3 - Article
AN - SCOPUS:0028338448
SN - 0960-894X
VL - 4
SP - 1381
EP - 1384
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 11
ER -
