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H
3
C
OH
HO
HO
O
N
H
3
C(H
2
C)
4
N
N
N
N
N
OH
O
O
HO
HO
O
n = 0-14
N
O
HO
n
N
N
OH
O
HO
HO
24
OH
23
FIGURE 12.10
1,6-oligomannose analogs having triazole bridges.
cancer and AIDS. The presently marketed antifungal and antibacterial drugs are
either highly toxic or becoming ineffective due to the appearance of resistant strains.
This necessitates continued research into new classes of antimicrobial agents. 1,2,3-
Triazole-containing molecules is one of these classes [53a].
A series of sugar modules carrying alkyne/azide functionality were synthesized by
glycosidase-mediated glycosylation of alkynyl alcohols and azide-containing alco-
hols with unprotected sugars in one step, and their subsequent click with a variety
of alkyne/azide counterparts resulted in triazole-containing glycosides (
25
) and their
subsequent submission to bioassays showed that this procedure is a feasible approach
to the development of antifungal drugs [53b].
Zhang et al. developed a facile synthetic strategy for the preparation of numerous
neomycin B derivatives (
26
) by modifications at the 5
position. The structure-activity
relationship (SAR) against aminoglycoside resistant bacteria equipped with vari-
ous aminoglycoside-modifying enzymes (AMEs) resulted into the identification of
numerous derivatives with an increased antibacterial activity compared to neomycin.
Prominent antibacterial activity against methicillin-resistant
Staphylococcus aureus
(MRSA) and vancomycin resistant
enterococci
(VRE) has been observed in some
compounds [54].
Reddy et al. have reported numerous glycal-derived tetrahydrofuran 1,2,3-triazoles
and screened them for antimicrobial activities. Among all, the compound (
28
) with a
MIC value of 25
g/mL exhibited potent antimicrobial activity whereas compound
(
27
) displayed significant antibacterial and antifungal activity with MIC value of
12.5
g/mL (Fig. 12.11) [13].
Tyrocidine (Tyc), a class of cyclic decapeptides possess antibacterial property due
to its ability to penetrate deep inside the lipid bilayer of cell membranes, however,
toxicity toward human blood and reproductive cells have anchored tremendous efforts
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