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RHN
N
N
N
NH
2
O
HN
HN
NH
OH
O
O
O
O
O
O
N
N
N
N
N
H
H
H
H
H
NH
2
O
O
O
O
O
HN
OH
HN
O
O
N
RHN
N
RHN
N
N
N
N
3
HO
HO
OH
OH
O
O
HO
HO
AcHN
O
AcHN
O
OH
HO
HO
OH
OH
O
N
O
CO
2
H
HO
O
AcHN
H
R
=
NH
Ac
O
AcHN
O
O
O
HO
HO
O
O
NHAc
O
HO
NH
Ac
OH
AcHN
O
O
HO
HO
O
3c
3
3
FIGURE 12.3
Glycosylated carrier protein (KLH) to derive synthetic anticancer vaccines.
inhibition against cell strains NCI-H
292
(lung carcinoma) and HEp-2 (larynx car-
cinoma) [41].
The tubulin/microtubule system is involved in the key step of mitosis, therefore
cell division can be prevented and apoptosis can be induced by disturbing their
dynamic equilibrium. To date, paclitaxel (taxol), discodermolide, or epothilones are
the most common microtubule-stabilizing antitubulin agents. Manach et al. synthe-
sized a library of paclitaxel (taxol) mimics (
9
) by stereoselective
-glycosylation of
L-glucurono-
-lactone followed by click reaction with aromatic azides. Synthesized
molecules were anticipated to serve as potential inhibitors of tubulin depolymeriza-
tion and showed cytotoxic properties (Fig. 12.5) [42].
Chen et al. using Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction of azide and
alkyne synthesized a
C
-3 symmetric (1-6)-
N
-acetyl-
-D-glucosamine octadecasac-
charide (
10
), which demonstrated significant antitumor activity against H22 in the
preliminary mice test (Fig. 12.6) [43].
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