171021-22-0Relevant articles and documents
Paclitaxel analogs modified in ring C: Synthesis and biological evaluation
Liang, Xian,Kingston, David G.I.,Long, Byron H.,Fairchild, Craig A.,Johnston, Kathy A.
, p. 3441 - 3456 (2007/10/03)
Lead tetracetate oxidation of 6α-hydroxy-7-epi-paclitaxel lends to C-nor-paclitaxel and C-seco-paclitaxel derivatives. Tetrpropylammonium perruthnate (TPAP) oxidation of a 6α-hydroxy-7-epi-paclitaxel derivative leads to a 6-formyl-C-nor-paclitaxel derivative. Reaction of a 6α-O-trifluoromethanesulfonyl-7-epi-paclitaxel derivative with DMAP yields a 20-O-acetyl-4-deacetyl-5,6-dehydro-6-formyl-C-nor-paclitaxel derivative. C-nor-paclitaxel analogs are less active than paclitaxel.
Synthesis, Structure Elucidation and Biological Evaluation of C-Norpaclitaxel
Liang, Xian,Kingston, David G. I.,Long, Byron H.,Fairchild, Craig A.,Johnston, Kathy A.
, p. 7795 - 7798 (2007/10/02)
Oxidation of 2'-TBDMS-6α-hydroxy-7-epipaclitaxel (1) with lead tetraacetate furnished 2'-TBDMS-C-norpaclitaxel (2) and the C-seco compound 3.Deprotection of 2 with pyridinium hydrofluoride yielded C-norpaclitaxel (4).C-norpaclitaxel (4) is less effective at promoting the assembly of microtubules and less cytotoxic towards HCT116 cells than paclitaxel.