A. Romani et al. / Bioorg. Med. Chem. Lett. 15 (2005) 4000–4003
4003
10. Experimental procedure for the preparation of a-7 and b-7
is as follows: To a solution of methylglucoside 5, acid 1
(2.2 equiv), DMAP (1.1 equiv), and DMAPÆHCl (1.1
equiv) in dry CH2Cl2, a solution of DCC (2.2 equiv) in dry
CH2Cl2 was added. The mixture was purged with N2 and
stirred for 19 h at rt, then cooled at À18 °C for 30 min and
filtered through celite. The organic phase was washed with
HCl 3%, brine, and H2O, dried over Na2SO4, and
concentrated. Purification of the residue by flash chroma-
tography (hexane/ethyl acetate = 10:1) afforded pure pro-
tected galloyl derivatives a-6 (26%), b-6 (16%) and a
combination of a + b fraction (13%). To a solution of a-6
(or b-6) in THF, a 1/1 mixture of n-Bu4NF/acetic acid (3
equiv) was added and the mixture was stirred at rt for 5 h,
then diluted with EtOAc, and poured into 1 M H3PO3.
The organic phase was washed with H2O and brine, dried
over Na2SO4, filtered and concentrated to provide the
desilylated galloyl derivative which was hydrogenated over
Pd/C 10% in THF. The hydrogenation was repeated twice
to complete the deprotection. The gray–green glassy solid
obtained was triturated with three portions of Et2O and
hexanes and purified by a reverse phase C-18 preparative
TLC. a-7. 1H NMR (CD3OD, 400 MHz) d (ppm): 3.47 (s,
3H), 3.62–3.71 (m, 2H), 3.76–3.79 (m, 1H), 4.28 (td,
J = 0.8, 6.4 Hz, 1H), 4.90 (s, 8H), 5.01–5.07 (m, 2H, H),
5.65–5.72 (m, 1H), 7.00 (s, 2H), 7.06 (s, 2H). 13C NMR
(CD3OD, 100 MHz) d (ppm): 55.6, 67.9, 69.8, 73.6, 74.3,
98.6, 110.3, 110.4, 120.6, 121.4, 140.0, 140.1, 146.3, 146.4,
167.6, 168.2. MS m/z (%): 497(100, MÀ), 345(65), 169(60),
(s, 2H). 13C NMR (CD3OD, 100 MHz) d (ppm) 57.3, 62.3,
69.8, 73.4, 77.0, 78.1, 103.2, 110.26, 110.32, 120.9, 121.1,
139.8, 139.9, 146.3, 146.34, 167.2, 167.9. MS m/z (%):
497(100, MÀ), 345(65), 169(60), 125(9).
11. Feldman, K. S.; Lawlor, M. D.; Sahasrabudhe, K. J. Org.
Chem. 2000, 65, 8011.
12. Candida albicans DBVPG 6133, Candida glabrata DBVPG
3828, and Issatchenkia orientalis DBVPG 6782; the yeast
species used as target microorganisms are represented by
their type strain and are conserved in the DBVPG Collec-
tion of Industrial Yeasts of the University of Perugia, Italy,
tained on YEPG (yeast extract 1%, peptone 1%, glucose
2%, and agar 1.5%) slants at 4 °C until use. Preliminary tests
on antimycotic activity of glucogalloyl esters were evalu-
ated by the agar diffusion well bioassay (ADWB).
13. Amphotericin B was purchased from Sigma (Sigma–
Aldrich, St. Louis, Mo, USA).
14. (a) MIC determination was carried out in 96-well micro-
plates (Corning Inc., USA) by a broth microdilution
method in agreement with the NCCLS recommendations;
(b) National Committee for Clinical Laboratory Stan-
dards. Approved Standard NCCLS Document M27-A.
Wayne Pa. 1997.
15. (a) Buzzini, P.; Martini, A. Med. Mycol. 2001, 39, 479; (b)
Hazen, K. C. Clin. Microbiol. Rev. 1995, 8, 462.
16. (a) Beggs, W. H.; Andrews, F. A.; Sarosi, G. A. Res.
Commun. Chem. Pathol. Pharmacol. 1978, 20, 409; (b)
Andrews, F. A.; Sarosi, G. A.; Beggs, W. H. J. Antimicrob.
Chemother. 1979, 5, 173; (c) Beggs, W. H.; Andrews, F. A.;
Sarosi, G. A. J. Antimicrob. Chemother. 1980, 6, 291; (d)
Brajtburg, J.; Elberg, S.; Kobayashi, G. S.; Medoff, G. J.
Antimicrob. Chemother. 1989, 24, 333.
1
125(9). b-7. H NMR (CD3OD, 400 MHz) d (ppm): 3.54
(s, 3H), 3.65–3.71 (m, 1H), 3.76–3.84 (m, 2H), 4.67 (d,
J = 8.0 Hz, 1H), 4.91 (s, 8H), 5.11 (dd, J = 8.0, 9.6 Hz,
1H), 5.42 (dd, J = 9.2 and 9.6 Hz, 1H), 6.98 (s, 2H), 7.02