D.-J. Fu et al.
Bioorganic Chemistry 107 (2021) 104634
0
0.5
1
2 μmol/L
PARP
cIAP1
cleaved-Parp
1.5
1.0
0.5
200
150
100
50
***
cleaved-PARP
*
**
**
cIAP1
***
Bax
0.0
1.5
0
0
0.5 μM 1 μM 2 μM
0
0.5 μM 1 μM 2 μM
Noxa
Bcl-xl
15
10
5
Noxa
Bcl2
****
1.0
0.5
0.0
**
****
Bcl-xl
0
0
0.5 μM 1 μM 2 μM
0
0.5 μM 1 μM 2 μM
cleaved-Caspase3
cleaved-Caspase8
cleaved-Caspase8
cleaved-Caspase3
80
60
40
20
0
40
30
20
10
0
****
****
Actin
***
0.5 μM 1 μM 2 μM
**
0.5 μM 1 μM 2 μM
***
*
0
0
Fig. 6. The effects of V7 on apoptosis proteins, MGC803 cells were treated with V7 for 48 h. The results shown were representative of three independent exper-
iments. *: p < 0.05 verse control. **: p < 0.01 verse control. ***: p < 0.001 verse control. ****: p < 0.0001 verse control.
(dd, J = 8.8, 2.4 Hz, 1H), 6.59 (s, 2H), 6.30 (d, J = 2.9 Hz, 1H), 4.84 (d, J
= 8.7 Hz, 4H), 3.74 (s, 3H), 3.70 (d, J = 13.2 Hz, 6H), 3.65 (s, 3H). 13C
NMR (100 MHz, DMSO‑d6) δ 167.40, 153.47, 153.10, 137.04, 136.36,
136.03, 131.79, 131.57, 130.18, 130.07, 128.36, 128.20, 110.93,
110.41, 105.86, 102.03, 100.41, 59.98, 56.00, 55.32, 51.83, 48.030.
HRMS (ESI) (m/z) [M + H]+ calcd for C27H28ClN2O5, 495.1687; found,
495.1689.
trimethoxyphenyl)acetamide (V6)
White solid, m.p.:96 ~ 97 ◦C, yield: 62%. 1H NMR (400 MHz,
DMSO‑d6) δ 7.15 (d, J = 8.9 Hz, 1H), 7.11 (s, 5H), 7.03 (d, J = 2.4 Hz,
1H), 6.75 (dd, J = 8.8, 2.4 Hz, 1H), 6.56 (s, 2H), 6.30 (d, J = 2.9 Hz, 1H),
4.84 (s, 2H), 4.79 (s, 2H), 3.75 (s, 3H), 3.69 (d, J = 8.9 Hz, 6H), 3.65 (s,
3H), 2.27 (s, 3H). 13C NMR (100 MHz, DMSO‑d6) δ 167.19, 153.46,
153.02, 136.97, 136.29, 136.16, 134.27, 131.56, 130.08, 128.76,
128.55, 128.37, 128.28, 110.92, 110.38, 105.92, 102.03, 100.38,
100.16, 59.98, 55.95, 55.32, 52.20, 48.04, 20.65. HRMS (ESI) (m/z) [M
+ H]+ calcd for C28H31N2O5, 475.2233; found, 475.2237.
N-(4-bromobenzyl)-2-(5-methoxy-1H-indol-1-yl)-N-(3,4,5-trime-
thoxyphenyl)acetamide (V4)
White solid, m.p.:119 ~ 121 ◦C, yield: 77%. 1H NMR (400 MHz,
DMSO‑d6) δ 7.50 (d, J = 8.3 Hz, 2H), 7.19 (dd, J = 15.3, 8.6 Hz, 3H),
7.11 (d, J = 2.9 Hz, 1H), 7.03 (d, J = 2.3 Hz, 1H), 6.75 (dd, J = 8.8, 2.4
Hz, 1H), 6.60 (s, 2H), 6.31 (d, J = 2.9 Hz, 1H), 4.85 (d, J = 8.6 Hz, 2H),
4.82 (s, 2H), 3.75 (s, 3H), 3.72 (s, 6H), 3.66 (s, 3H). 13C NMR (100 MHz,
DMSO‑d6) δ 167.41, 153.49, 153.12, 137.07, 136.78, 136.04, 131.58,
131.12, 130.54, 130.06, 128.37, 120.32, 110.95, 110.41, 105.87,
102.04, 100.42, 59.98, 56.00, 55.32, 51.92, 48.04. HRMS (ESI) (m/z)
[M + H]+ calcd for C27H28BrN2O5, 539.1182; found, 539.1187.
N-(3-fluorobenzyl)-2-(5-methoxy-1H-indol-1-yl)-N-(3,4,5-trime-
thoxyphenyl)acetamide (V5)
2-(5-Methoxy-1H-indol-1-yl)-N-(4-methoxybenzyl)-N-(3,4,5-tri-
methoxyphenyl)acetamide (V7)
White solid, m.p.:103 ~ 104 ◦C, yield: 50%. 1H NMR (400 MHz,
DMSO‑d6) δ 7.17 – 7.09 (m, 4H), 7.03 (d, J = 2.3 Hz, 1H), 6.86 (d, J =
8.5 Hz, 2H), 6.74 (dt, J = 11.9, 6.0 Hz, 1H), 6.52 (s, 2H), 6.30 (d, J = 3.0
Hz, 1H), 4.80 (d, J = 13.3 Hz, 2H), 4.76 (s, 2H), 3.74 (s, 3H), 3.71 (d, J =
8.6 Hz, 9H), 3.65 (s, 3H). 13C NMR (100 MHz, DMSO‑d6) δ 178.96,
168.05, 162.86, 156.28, 152.78, 149.30, 139.04, 136.65, 133.86,
129.86, 129.24, 128.61, 125.30, 124.70, 124.13, 120.40, 34.84, 30.79.
HRMS (ESI) (m/z) [M + H]+ calcd for C28H31N2O6, 491.2182; found,
491.2189.
White solid, m.p.:114 ~ 115 ◦C, yield: 45%. 1H NMR (400 MHz,
DMSO‑d6) δ 7.38 – 7.31 (m, 1H), 7.18 (d, J = 8.9 Hz, 1H), 7.11 (dd, J =
8.1, 4.2 Hz, 2H), 7.08 (d, J = 6.5 Hz, 2H), 7.03 (d, J = 2.3 Hz, 1H), 6.75
(dd, J = 8.8, 2.4 Hz, 1H), 6.63 (s, 2H), 6.31 (d, J = 2.9 Hz, 1H), 4.87 (d, J
= 6.8 Hz, 4H), 3.75 (s, 3H), 3.72 (s, 6H), 3.66 (s, 3H). 13C NMR (100
MHz, DMSO‑d6) δ 167.52, 163.32, 160.90, 153.48, 153.11, 140.32,
140.25, 137.06, 136.08, 131.58, 130.21, 130.13, 130.08, 128.38,
124.24, 114.94, 114.73, 114.06, 113.85, 110.93, 110.43, 105.85,
102.03, 100.42, 59.97, 55.99, 55.31, 52.03, 48.05. HRMS (ESI) (m/z)
[M + H]+ calcd for C27H28FN2O5, 479.1982; found, 479.1989.
2-(5-Methoxy-1H-indol-1-yl)-N-(4-methylbenzyl)-N-(3,4,5-
2-(5-Methoxy-1H-indol-1-yl)-N-(3-methylbenzyl)-N-(3,4,5-trime-
thoxyphenyl)acetamide (V8)
White solid, m.p.:115 ~ 116 ◦C, yield: 72%. 1H NMR (400 MHz,
DMSO‑d6) δ 7.21 – 7.14 (m, 2H), 7.05 (dt, J = 12.0, 10.6 Hz, 5H), 6.75
(dd, J = 8.8, 2.2 Hz, 1H), 6.56 (s, 2H), 6.30 (d, J = 2.8 Hz, 1H), 4.86 (s,
2H), 4.80 (s, 2H), 3.75 (s, 3H), 3.70 (s, 6H), 3.65 (s, 3H), 2.27 (s, 3H).
13C NMR (100 MHz, DMSO‑d6) δ 167.25, 153.49, 153.02, 137.32,
137.25, 137.02, 136.20, 131.54, 130.09, 128.83, 128.40, 128.11,
127.77, 125.35, 110.93, 110.36, 105.91, 102.08, 100.38, 59.98, 55.94,
55.34, 52.42, 48.12, 20.90. HRMS (ESI) (m/z) [M + H]+ calcd for
7