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4.3.1. Physicochemical and spectroscopic data for the
compound (7)
4.4. General procedure for deacetylation
Syrupy liquid; Yield: 92% (1.33 g); Rf = 0.53 (CHCl3–MeOH, 9:1);
1H NMR (300 MHz, CDCl3): d 8.22 (s, 2H, –NH), 7.39–6.83 (m, 16H,
Ar-H), 5.00–4.84 (m, 4H, Sac-H), 4.58 (t, J = 10.2 Hz, 2H, Sac-H),
4.25–4.20 (q, J = 7.8 Hz, 2H, Hb), 4.10 (t, J = 4.2 Hz, 4H, –OCH2),
4.01–3.97 (m, 2H, Sac-H), 3.86 (t, J = 4.7 Hz, 4H, –OCH2), 3.82–
3.77 (dd, J = 2.7 Hz, J = 9.5 Hz, 2H, -Sac-H), 3.75 (s, 4H, –OCH2),
3.71 (d, J = 9.5 Hz, 2H, Ha), 3.67–3.59 (dd, J = 7.8 Hz, J = 17.1 Hz,
4H, –CH2), 3.48–3.36 (m, 4H, –CH2), 2.01 (s, 6H, –NCH3), 1.97–
1.94 (m, 24H, –COCH3); 13C NMR (75 MHz, CDCl3): d 204.0, 179.3,
170.6, 170.2 (2C), 169.5, 157.8, 157.7, 141.0, 133.8, 133.7, 129.4,
129.1, 128.9, 127.1, 126.9, 123.2, 123.1, 114.8, 109.8, 75.3, 74.2,
73.9, 72.6, 71.0, 70.8, 69.8, 68.2, 67.4, 62.0, 61.5, 60.8, 44.2, 43.2,
34.8, 20.8, 20.7, 20.6; Anal. Calcd for C74H86N4O26 : C, 61.40; H,
5.99; N, 3.87. Found: C, 61.11; H, 6.17; N, 3.72.
To the solution of acetylated compound 7 (1 mmol) dissolved in
anhydrous methanol, 5% of NaOMe dissolved in MeOH was added.
The reaction mixture was stirred at room temperature for about
6 h. To the reaction mixture, water was added followed by the
addition of ion exchange resin Amberlite IR-120 (H+). The resultant
solution was then filtered and solvent was removed under reduced
pressure and the crude product was subjected to column chroma-
tography (chloroform–methanol).
4.4.1. Physicochemical and spectroscopic data for the
compound (12)
Brown solid; mp: 113 °C; Yield: 94% (1.04 g); Rf = 0.53 (CHCl3–
MeOH, 8:2); 1H NMR (300 MHz, CDCl3 + DMSO): d 7.95 (s, 2H, –
NH), 7.24–6.66 (m, 16H, Ar-H), 4.80–5.00 (m, 2H, Sac-H), 4.58 (m,
2H, Sac-H), 3.98–3.90 (m, 6H, –OCH2, Hb), 3.80–3.70 (m, 4H, Ha,
Sac-H), 3.64 (t, J = 4.4 Hz, 4H, –OCH2), 3.53–3.29 (m, 12H, –OCH2,
Sac-H), 3.21 (t, J = 6.6 Hz, 2H, Sac-H), 3.12 (t, J = 8.0 Hz, 2H, Sac-
H), 3.04–2.91 (m, 2H, Sac-H), 2.71–2.69 (m, 2H, Sac-H), 2.60–2.55
(m, 2H, Sac-H), 1.90 (s, 6H, –NCH3); 13C NMR (75 MHz, CDCl3): d
211.3, 184.6, 162.2, 138.9, 134.2, 132.0, 131.7, 131.0, 130.8,
127.2, 119.1, 118.7, 115.2, 84.6, 81.6, 80.0, 78.1, 78.0, 77.7, 77.5,
75.3, 74.8, 74.6, 74.3, 72.5, 72.2, 65.5, 50.9, 50.1, 47.8, 47.6, 39.5;
Anal. Calcd for C58H70N4O18: C, 62.69; H, 6.35; N, 5.04. Found: C,
62.97; H, 6.51; N, 4.92.
4.3.2. Physicochemical and spectroscopic data for the
compound (8)
White solid; mp: 115–117 °C; Yield: 86% (1.11 g); Rf = 0.43
(CHCl3–MeOH, 9:1); 1H NMR (300 MHz, CDCl3): d 7.96 (s, 2H, –
NH), 7.36–7.02 (m, 16H, Ar-H), 5.01–4.87 (m, 4H, Sac-H), 4.59 (t,
J = 9.3 Hz, 2H, Sac-H), 4.24–4.18 (q, J = 8.7 Hz, 2H, Hb), 4.10 (s, 6H,
–OCH2, Sac-H), 3.86 (m, 6H, –OCH2, Sac-H), 3.76 (s, 8H, –OCH2,
Sac-H), 3.71–3.56 (m, 4H, Ha, Sac-H), 3.48–3.36 (m, 4H, Sac-H),
2.17 (s, 6H, –NCH3), 2.01–1.94 (m, 18H, –COCH3); 13C NMR
(75 MHz, CDCl3): d 204.1, 179.1, 170.7, 170.2, 169.4, 129.4, 129.1,
128.9, 126.5, 123.2, 123.1, 114.8, 114.7, 109.8, 75.3, 74.2, 73.9,
72.6, 71.0, 70.8, 69.8, 68.2, 67.5, 61.9, 61.5, 60.8, 45.3, 44.3, 34.8,
20.7, 20.6; Anal. Calcd for C68H78N4O22 : C, 62.66; H, 6.03; N,
4.30. Found: C, 62.92; H, 5.84; N, 4.13.
4.5. Antimicrobial assay
The in vitro antimicrobial activities of test compounds were
determined by the well diffusion method. Muller Hinton Agar
(MHA) medium was used for preparation of plates. The medium
was poured to the sterile petriplates of 90 mm diameter. The agar
was allowed to set at ambient temperature. Fresh bacterial
cultures of two Gram positive bacteria, Staphylococcus aureus
and Bacillus subtilis and three Gram negative bacteria, Pseudomo-
nas aeruginosa, Klebsiella pneumoniae and Proteus vulgaris were
spread on the surface of the MHA plate with the swab. After incu-
bation, the MHA plates were allowed for the pre-incubation for
10 min. using a sterile cork borer, the well was cut from the agar
in the plate. The compounds were weighed, dissolved in dimethyl
sulfoxide (DMSO) (10 mg/mL) and were poured corresponding to
4.3.3. Physicochemical and spectroscopic data for the
compound (10)
Light yellow solid; mp: 124–128 °C; Yield: 85% (1.32 g);
Rf = 0.66 (CHCl3–MeOH, 9:1); 1H NMR (300 MHz, CDCl3): d 8.31
(s, 2H, –NH), 7.29–6.78 (m, 16H, Ar-H), 4.94–4.81 (m, 4H, Sac-H),
4.53 (t, J = 4.8 Hz, 2H, Sac-H), 4.12 (d, J = 11.4 Hz, 2H, Ha), 4.04–
3.95 (m, 8H, –OCH2, Hc), 3.79–3.78 (m, 4H, –OCH2), 3.67 (m, 6H,
–OCH2, Sac-H), 3.61–3.48 (m, 6H, –NCH2, Hb), 3.29 (t, J = 10.7 Hz,
2H, Sac-H), 2.62–2.54 (m, 6H, –CH2, Sac-H), 2.34–2.22 (m, 4H, –
CH2), 1.88–1.85 (m, 28H, –COCH3, –CH2); 13C NMR (75 MHz,
CDCl3): d 203.0, 201.8, 170.7, 170.2, 169.6, 169.4, 157.9, 131.4,
129.9, 129.0, 128.8, 127.3, 127.0, 122.5, 114.9, 110.7, 75.2, 74.3,
74.0, 73.5, 72.5, 71.0, 70.9, 69.8, 68.2, 67.5, 61.9, 61.7, 43.9, 31.6,
30.5, 27.1, 22.6, 20.8, 20.7, 20.5, 14.1, 11.4; Anal. Calcd for
25, 50, 75 and 100 lL of this test solution. The inoculated plates
were initially incubated for 15 min at room temperature, and then
they were incubated at 37 °C for 24 h. Turbidity was adjusted with
sterile broth so as to correspond to 0.5 McFarland standards. Then,
the plates were examined for any zone of growth inhibition. Inhi-
bition zones were recorded as the diameter of growth free zones
including the diameter of the well in mm at the end of incubation
period.
C78H90N4O26 : C, 62.47; H, 6.05; N, 3.74. Found: C, 62.71; H, 6.23;
N, 3.60.
4.3.4. Physicochemical and spectroscopic data for the
compound (11)
Pale pink solid; mp: 96–100 °C; Yield: 88% (1.16 g); Rf = 0.45
(CHCl3–MeOH, 9:1); 1H NMR (300 MHz, CDCl3): d 8.40 (s, 2H, –
NH), 7.35–6.87 (m, 16H, Ar-H), 5.00–4.93 (m, 4H, Sac-H), 4.84–
4.77 (m, 2H, Sac-H), 4.58–4.46 (m, 2H, Sac-H), 4.22 (d, J = 12.0 Hz,
2H, Ha), 4.12 (s, 4H, –OCH2), 4.02–3.97 (m, 2H, Hc), 3.86 (t,
J = 4.7 Hz, 4H, –OCH2), 3.76 (s, 4H, –OCH2), 3.66–3.55 (m, 4H, -Hb,
Sac-H), 3.49–3.43 (m, 4H, –CH2), 2.97 (t, J = 11.0 Hz, 2H, Sac-H),
2.60–2.54 (m, 6H, Sac-H, –CH2), 2.33–2.24 (m, 4H, –CH2), 1.99–
1.96 (m, 24H, –COCH3); 13C NMR (75 MHz, CDCl3): d 203.5, 180.5,
172.3, 170.2, 169.8, 157.7, 141.2, 131.8, 129.6, 129.0, 128.7,
127.0, 125.6, 122.5, 114.8, 110.5, 74.3, 73.5, 72.6, 71.3, 70.8, 69.8,
69.1, 67.4, 66.3, 56.2, 51.8, 47.8, 44.0, 31.1, 30.7, 27.3, 21.1, 20.6
(2C), 18.2, 10.5; Anal. Calcd for C72H82N4O22 : C, 63.80; H, 6.10;
N, 4.13. Found: C, 63.65; H, 5.92; N, 4.00.
Acknowledgements
Authors acknowledge SERC-DST, New Delhi, India for financial
support. T. M. thank DST, New Delhi for 300 MHz NMR facility
under DST-FIST programme to the Department of Organic Chem-
istry, University of Madras, Guindy Campus, Chennai, India. A. H.
thanks CSIR, New Delhi for JRF and S. N. thanks CSIR, New Delhi
for SRF.
Supplementary data
Supplementary data associated with this article can be found, in