X.-z. Gao et al.
Bioorganic Chemistry 109 (2021) 104694
1H), 6.85 (d, J = 7.7 Hz, 2H), 6.81 (dd, J = 8.3, 2.5 Hz, 1H), 6.56 (s, 1H),
6.46 (s, 1H), 6.40 (s,1H), 6.33 (dd, J = 8.3, 2.0 Hz, 1H), 6.04 (s, 1H),
3.92 (s, 3H), 3.78 (s, 3H), 3.70 (dd, J = 22.5, 12.4 Hz, 2H), 3.52 (dd, J =
16.1, 12.9 Hz,2H), 3.43–3.36 (m, 3H), 2.99 (tdd, J = 18.0, 13.2, 6.7 Hz,
6H), 2.87 (d, J = 8.4 Hz, 3H), 2.81 (dd, J = 13.8, 6.1 Hz, 2H), 2.69 (d, J
= 9.0 Hz, 3H), 2.60–2.45 (m, 2H), 2.30 (s, 3H); 13C NMR (101 MHz,
CDCl3) δ 154.05, 150.13, 149.26, 148.93, 148.67, 147.04, 142.47,
134.36, 133.63, 132.65, 130.52, 127.64, 127.09, 125.34 , 123.40,
122.98, 122.30, 122.05, 121.91, 115.88, 112.33, 111.54, 106.14, 64.38,
61.37, 56.10, 56.01, 55.80, 45.84, 44.89, 43.77, 42.29, 41.83, 41.37,
39.53, 39.12, 23.39, 22.12; HRMS (ESI): calcd for C38H42N2O8S m/z:
686.2662, found: 687.2711 [M + H]+. Yield: 95.4%.
43.80, 42.37, 39.64, 24.33, 22.00; HRMS (ESI): calcd for
C43H43BrN2O8S m/z: 826.1923, found: 827.1965 [M + H]+. Yield:
83.5%.
4 h 7-O-(2-F-benzene-sulfonyl)-d-Tet as a light-yellow powder. 1H
NMR (400 MHz, CDCl3) δ 7.63 (d, J = 6.8 Hz, 2H), 7.40–7.07 (m, 5H),
6.86 (s, 2H), 6.75 (d, J = 7.8 Hz, 1H), 6.49 (s, 2H), 6.26 (d, J = 13.2 Hz,
2H), 3.91 (s, 3H), 3.67 (t, J = 10.0 Hz, 2H), 3.48 (d, J = 10.5 Hz, 2H),
3.38 (s, 3H), 3.30 (s, 3H), 2.79 (ddd, J = 33.4, 22.7, 13.2 Hz, 8H), 2.60
(s, 3H), 2.57–2.34 (m, 2H), 2.28 (s, 3H); 13C NMR (101 MHz, CDCl3) δ
166.95, 153.77, 150.89, 149.39, 148.74, 147.81, 147.14, 142.32,
134.98, 134.45, 133.49, 132.61, 131.43, 130.22, 128.31, 128.11,
127.74, 123.84, 122.82, 121.85, 120.72, 116.02, 115.96, 115.79,
112.73, 111.52, 106.04, 63.98, 61.35, 56.13, 55.77, 45.05, 43.85,
42.39, 42.09, 39.20, 24.49, 22.08; HRMS (ESI): calcd for C43H43FN2O8S
m/z: 766.2724, found: 767.2717 [M + H]+. Yield: 89.3%.
4d 7-O-(CH2CH3-sulfonyl)-d-Tet as a light-yellow powder. 1H NMR
(400 MHz, CDCl3) δ 7.36 (dd, J = 8.2, 1.9 Hz, 1H), 7.14 (dd, J = 8.2, 2.4
Hz, 1H), 6.82 (dt, J = 8.3, 5.3 Hz, 3H), 6.51 (d, J = 16.7 Hz, 2H),
6.42–6.30 (m, 2H), 6.04 (s, 1H), 3.92 (s, 3H), 3.88–3.81 (m, 1H),
3.81–3.73 (m, 3H), 3.69 (s, 1H), 3.62–3.41 (m, 3H), 3.37 (d, J = 11.3 Hz,
3H), 3.31–3.11 (m, 2H), 3.08–2.64 (m, 10H), 2.59 (s, 3H), 2.47 (ddd, J
= 36.1, 25.3, 16.1 Hz, 2H), 2.35–2.23 (m, 3H), 1.26 (t, J = 7.4 Hz, 3H);
13C NMR (101 MHz, CDCl3) δ 153.58, 150.32, 149.36, 148.89, 148.10,
146.92, 142.25, 135.08, 134.46, 132.51, 132.40, 130.42,
128.47,128.30, 127.70, 123.67, 122.78, 122.12, 121.94, 121.41,
115.79, 112.60, 111.39, 106.14, 63.94, 61.37, 56.08, 56.06, 55.86,
46.42, 46.02, 45.14, 43.71, 42.46, 42.30, 41.47, 38.94, 24.77, 22.14;
HRMS (ESI): calcd for C39H44N2O8S m/z: 700.2818, found: 701.2892
[M + H]+. Yield: 90.6%.
4i 7-O-(4-Cl-benzene-sulfonyl)-d-Tet as a white powder. 1H NMR
(400 MHz, CDCl3) δ 7.52 (d, J = 8.6 Hz, 2H), 7.47–7.27 (m, 4H), 7.11
(dd, J = 8.1, 2.4 Hz, 1H), 6.79 (s, 2H), 6.68 (dd, J = 8.2, 2.4 Hz, 1H),
6.37 (d, J = 12.4 Hz, 2H), 6.26–6.18 (m, 2H), 3.86 (s, 3H), 3.62–3.54 (m,
2H), 3.45 (s, 3H), 3.33 (ddd, J = 23.1, 12.3, 8.9 Hz, 2H), 3.21 (s, 3H),
2.92–2.62 (m, 8H), 2.57 (s, 3H), 2.49–2.37 (m, 2H), 2.20 (s, 3H); 13C
NMR (101 MHz, CDCl3) δ 153.64, 150.93, 149.42, 148.61, 147.68,
147.10, 142.23, 140.15, 135.93, 135.10, 134.40, 132.60, 130.30,
130.05, 129.34, 128.92, 128.50, 128.37, 128.21, 128.02, 123.80,
122.77, 121.87, 120.41, 115.80, 112.79, 111.49, 106.13, 63.96, 61.37,
56.07, 55.79, 53.54, 45.08, 43.84, 42.54, 42.34, 42.04, 39.15, 24.58,
22.12; HRMS (ESI): calcd for C43H43ClN2O8S m/z: 782.2829, found:
783.2862 [M + H]+. Yield: 81.2%.
4e 7-O-(CH3CH2CH2-sulfonyl)-d-Tet as a light-yellow powder. 1H
NMR (400 MHz, CDCl3) δ 7.29 (dd, J = 8.2, 1.9 Hz, 1H), 7.06 (dd, J =
8.1, 2.4 Hz, 1H), 6.74 (dt, J = 8.3, 5.4 Hz, 3H), 6.43 (d, J = 14.0 Hz, 2H),
6.36–6.19 (m, 2H), 5.96 (s, 1H), 3.84 (s, 3H), 3.76 (dd, J = 11.1, 5.3 Hz,
0H), 3.73–3.65 (m, 3H), 3.62 (d, J = 9.7 Hz, 0H), 3.40 (ddd, J = 11.9,
9.6, 5.7 Hz, 1H), 3.26 (d, J = 14.9 Hz, 3H), 2.93–2.74 (m, 2H),
2.70–2.59 (m, 1H), 2.57–2.45 (m, 1H), 2.23 (d, J = 16.7 Hz, 1H),
1.76–1.57 (m, 1H), 0.89 (t, J = 7.5 Hz, 1H); 13C NMR (101 MHz, CDCl3)
δ 153.60, 150.38, 149.37, 148.97, 148.10, 146.92, 142.25, 135.16,
134.52, 132.46, 130.42, 128.42, 127.63, 123.67, 122.78, 122.15,
121.95, 121.55, 115.84, 112.60, 111.38, 106.14, 64.04, 61.39, 56.09,
56.08, 55.87, 53.46, 45.19, 43.74, 42.41, 41.52, 39.23, 29.72, 24.73,
22.11, 17.16, 12.91; HRMS (ESI): calcd for C40H46N2O8S m/z: 714.2975,
found: 715.3008 [M + H]+. Yield: 91.5%.
4j 7-O-(2-Naphthalene-sulfonyl)-d-Tet as a light-yellow powder. 1H
NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 8.02–7.75 (m, 4H), 7.69 (t, J =
7.5 Hz, 1H), 7.56 (dd, J = 15.4, 8.1 Hz, 2H), 6.85–6.73 (m, 3H), 6.61 (d,
J = 7.4 Hz, 1H), 6.54 (dd, J = 8.2, 2.1 Hz, 1H), 6.30 (d, J = 23.5 Hz, 2H),
6.21 (s, 1H), 6.03 (d, J = 8.2 Hz, 1H), 4.40 (s, 1H), 3.84 (s, 3H), 3.53 (d,
J = 10.0 Hz, 1H), 3.45 (d, J = 10.1 Hz, 3H), 3.33 (ddd, J = 21.6, 20.7,
10.6 Hz, 2H), 3.19 (d, J = 14.4 Hz, 3H), 2.94–2.68 (m, 6H), 2.53 (s, 3H),
2.51–2.31 (m, 4H), 2.20 (d, J = 12.1 Hz, 3H); 13C NMR (101 MHz,
CDCl3) δ 153.47, 151.48, 149.29, 148.57, 147.57, 147.12, 142.42,
135.28, 134.63, 134.59, 134.47, 132.42, 131.87, 129.97, 129.52,
128.73, 128.08, 127.79, 127.59, 123.85, 122.83, 121.50, 120.04,
115.89, 112.84, 111.47, 106.42, 63.42, 61.42, 56.12, 56.59, 55.77,
44.96, 43.91, 42.41, 42.32, 42.23, 39.05, 24.34, 22.05; HRMS (ESI):
calcd for C47H46N2O8S m/z: 798.2975, found: 799.3029 [M + H]+.
Yield: 82.4%.
1
4f 7-O-(benzene-sulfonyl)-d-Tet as a light-yellow powder. H NMR
(400 MHz, CDCl3) δ 7.66 (dd, J = 15.5, 7.8 Hz, 4H), 7.47 (t, J = 7.4
Hz,2H), 7.33 (d, J = 8.1 Hz, 1H), 7.16 (dd, J = 8.1, 1.4 Hz, 1H), 6.88 (s,
2H), 6.78–6.72 (m, 1H), 6.51–6.44 (m, 2H), 6.32–6.20 (m, 2H), 3.93 (s,
3H), 3.69 (dd, J = 15.9, 7.6 Hz, 2H), 3.52 (dd, J = 19.7, 9.0 Hz, 2H),
3.44 (s, 3H), 3.27 (d, J = 12.0 Hz, 3H), 3.26–3.12 (m, 2H), 2.97–2.87 (m,
4H), 2.74 (dd, J = 16.4, 7.2 Hz, 2H), 2.63 (d, J = 6.5 Hz, 4H), 2.47 (dd, J
= 17.6, 12.5 Hz, 2H), 2.29 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 153.75,
150.99, 149.31, 148.87, 147.75, 147.12, 142.39 ,137.39, 135.25,
135.03, 134.60, 133.56, 132.52, 130.25, 128.58, 128.36, 128.19,
128.11, 123.77, 122.85, 121.69, 121.03, 116.08, 112.70, 111.52,
106.00, 77.45, 77.19, 76.87, 63.87, 61.37, 56.13, 55.78, 55.69, 45.08,
43.85, 42.39, 42.03, 39.77, 24.30, 22.04; HRMS (ESI): calcd for
4.2. Cell culture
A549, HeLa, MCF-7, HepG-2, and H460 cells were purchased from
the Cell Bank of Type Culture Collection of the Chinese Academy of
Sciences (Shanghai, China). H520 cells and BEAS-2B cells were pur-
chased from the American Type Culture Collection (ATCC; Manassas,
VA, USA). The cells were maintained in medium (HyClone) containing
10% fetal bovine serum (Gibco) and 100 U/mL penicillin–streptomycin
(HyClone). All cells were cultured under humid conditions at 37 ℃, 95%
air and 5% CO2.
C
43H44N2O8S m/z: 748.2852 found: 749.2864 [M + H]+. Yield: 87.8%.
4 g 7-O-(2-Br-benzene-sulfonyl)-d-Tet as a light-yellow powder. 1H
NMR (400 MHz, CDCl3) δ 7.79 (t, J = 1.6 Hz, 1H), 7.70 (d, J = 8.0 Hz,
1H), 7.51 (d, J = 8.0 Hz, 1H), 7.38–7.16 (m, 3H), 7.10 (dd, J = 8.1, 2.5
Hz, 1H), 6.83–6.77 (m, 2H), 6.66 (dd, J = 8.3, 2.5 Hz, 1H), 6.38 (d, J =
7.2 Hz, 2H), 6.25 (s, 1H), 6.17 (dd, J = 8.3, 2.0 Hz, 1H), 3.83 (d, J = 9.4
Hz, 3H), 3.65 (dd, J = 11.1, 5.4 Hz, 1H), 3.57 (d, J = 9.9 Hz, 1H), 3.45 (s,
3H), 3.43–3.31 (m, 2H), 3.20 (s, 3H), 2.96–2.59 (m, 8H), 2.55 (s, 3H),
2.43 (dd, J = 30.0, 9.4 Hz, 2H), 2.20 (s, 3H); 13C NMR (101 MHz, CDCl3)
δ 153.77, 150.96, 149.26, 148.70, 147.61, 147.12, 142.29, 139.25,
136.62, 135.06, 134.51, 132.69, 131.39, 130.17, 128.53, 128.32,
127.98, 127.22, 123.98, 122.85, 122.46, 121.77, 120.61, 116.26,
112.81, 111.47, 106.22, 63.74, 61.38, 56.11, 55.80, 46.14, 45.02,
4.3. CCK-8 assays
A549 cells in the logarithmic growth phase were seeded on a 96-well
plate for 12 h at a density of 5000 cells/well. The cells were treated with
different concentrations of 20, 10, 5, 2.5, 1.25, 0.625 and 0.165 µM for
24, 48, and 72 h. At the end of the incubation, 10 µL of CCK-8 (10 mg/
mL) and 90 µL of the medium were added to each pore, and the plate was
placed at 37 ◦C for 2 h. The absorbance was measured at 450 nm using a
microplate reader (BIO-RAD, USA).
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