MedChemComm
Research Article
56.1, 55.3, 54.4, 48.6, 47.4, 42.7, 39.9, 39.6, 39.1, 38.4, 37.7, 37.0,
36.8, 32.7, 30.9, 28.0, 27.9, 25.2, 23.6, 23.5, 23.2, 21.3, 21.2, 18.1,
17.3, 17.0, 16.7, 15.6. HR-MS (m/z) (ESI): calcd for C41H61NO6 [M
+ H+]: 663.4499; found: 664.4547.
105.2, 80.8, 55.3, 55.2, 54.4, 48.7, 47.5, 42.7, 39.9, 39.6, 39.1,
38.4, 37.7, 37.1, 36.8, 32.7, 30.9, 28.1, 27.9, 25.2, 23.6, 23.5,
23.3, 21.3, 21.2, 18.1, 17.3, 16.8, 16.7, 15.6. HR-MS (m/z) (ESI):
calcd for C39H57NO4 [M + H+]: 603.4288; found: 604.4342.
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Compound 5Y2. Yield 85.6%; H NMR (400 MHz, DMSO)
Compound 5Y7. Yield 88.2%; H NMR (400 MHz, CDCl3) δ
δ 8.68 (s, 1H, –CONH–), 7.21 (d, J = 2.1 Hz, 1H), 7.08 (dd, J =
8.7, 2.1 Hz, 1H), 6.84 (d, J = 8.8 Hz, 1H), 5.30 (s, 1H), 4.40
(dd, J = 11.2, 4.5 Hz, 1H), 3.70 (d, J = 1.9 Hz, 6H), 2.00 (s,
3H), 1.09 (s, 3H), 0.96 (s, 3H), 0.89–0.85 (m, 6H), 0.81 (d, J =
4.8 Hz, 6H), 0.67 (s, 3H). 13C NMR (101 MHz, DMSO) δ 175.2
(–CONH–), 170.5 (–COO–), 148.8, 145.2, 139.1, 133.4, 124.9,
112.8, 112.3, 106.2, 80.4, 56.2, 55.8, 55.0, 52.2, 47.9, 47.3,
42.1, 39.3, 38.8, 38.2, 37.7, 36.9, 32.9, 30.8, 28.3, 27.9, 23.9,
24.0, 23.71, 23.4, 21.6, 21.4, 18.2, 17.6, 17.1, 17.1, 15.6. HR-
MS (m/z) (ESI): calcd for C40H59NO5 [M + H+]: 633.4393;
found: 634.4429.
7.65 (s, 1H, –CONH–), 7.40 (s, 1H), 7.19–7.11 (m, 2H), 6.88 (d,
J = 6.6 Hz, 1H), 5.48 (s, 1H), 4.49 (dd, J = 10.1, 5.3 Hz, 1H),
2.31 (s, 3H), 2.03 (s, 3H), 1.13 (s, 3H), 0.98 (s, 3H), 0.94–0.89
(m, 6H), 0.84 (d, J = 10.0 Hz, 6H), 0.70 (s, 3H). 13C NMR (101
MHz, CDCl3) δ 176.2 (–CONH–), 171.0 (–COO–), 140.1,
138.78, 138.1, 128.6, 126.0, 124.8, 120.4, 116.7, 80.9, 77.4,
77.3, 77.1, 76.7, 55.3, 54.3, 48.6, 47.5, 42.6, 39.9, 39.6, 39.1,
38.4, 37.7, 37.1, 36.8, 32.7, 30.9, 28.1, 27.9, 25.1, 23.6, 23.6,
23.3, 21.5, 21.3, 21.2, 18.1, 17.3, 16.9, 16.7, 15.6. HR-MS (m/z)
(ESI): calcd for C39H57NO3 [M + H+]: 587.4338; found:
588.4400.
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Compound 5Y3. Yield 89.0%; H NMR (400 MHz, CDCl3) δ
Compound 5Y8. Yield 89.7%; H NMR (400 MHz, CDCl3) δ
7.59 (s, 1H, –CONH–), 7.34 (s, 1H), 7.08 (d, J = 7.8 Hz, 1H),
7.02 (d, J = 8.0 Hz, 1H), 5.47 (s, 1H), 4.54–4.43 (m, 1H), 2.21
(d, J = 10.3 Hz, 6H), 2.04 (s, 3H), 1.12 (s, 3H), 0.97 (s, 3H), 0.91
(d, J = 8.8 Hz, 6H), 0.84 (d, J = 10.0 Hz, 6H), 0.71 (s, 3H). 13C
NMR (101 MHz, CDCl3) δ 176.1 (–CONH–), 171.0 (–COO–),
140.1, 137.1, 135.9, 132.2, 129.8, 125.9, 121.1, 117.1, 80.9,
55.3, 54.3, 48.5, 47.5, 42.6, 39.9, 39.6, 39.2, 38.4, 37.7, 37.1,
36.8, 32.7, 30.9, 28.1, 27.9, 25.1, 23.6, 23.3, 21.3, 21.2, 19.9,
19.2, 18.1, 17.3, 16.9, 16.7, 15.6. HR-MS (m/z) (ESI): calcd for
C40H59NO3 [M + H+]: 601.4495; found: 602.4549.
6.61 (s, 1H, –CONH–), 5.29 (s, 1H), 4.47 (dd, J = 9.9, 5.9 Hz,
1H), 3.82 (s, 2H), 2.50 (t, J = 4.8 Hz, 2H), 2.32 (s, 6H), 2.02 (s,
3H), 1.07 (s, 3H), 0.92 (s, 6H), 0.87–0.82 (m, 9H), 0.76 (s, 3H).
13C NMR (101 MHz, CDCl3) δ 178.3 (–CONH–), 171.0 (–COO–),
139.2, 125.7, 80.9, 57.7, 55.3, 53.7, 47.7, 47.5, 44.9, 42.4, 39.7,
39.6, 39.0, 38.3, 37.7, 37.2, 36.8, 36.4, 32.8, 30.9, 28.1, 27.9,
24.7, 23.5, 23.4, 23.2, 21.3, 21.2, 18.2, 17.2, 17.0, 16.7, 15.5.
HR-MS (m/z) (ESI): calcd for C36H60N2O3 [M + H+]: 568.4604;
found: 569.4658.
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Compound 5Y9. Yield 90.1%; H NMR (400 MHz, CDCl3) δ
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Compound 5Y4. Yield 84.7%; H NMR (400 MHz, CDCl3) δ
5.19 (s, 1H), 4.50–4.44 (m, 1H), 3.74 (d, J = 68.0 Hz, 8H), 2.33
(s, 3H), 2.02 (s, 3H), 1.05 (s, 6H), 0.92 (d, J = 4.7 Hz, 6H), 0.83
(d, J = 4.4 Hz, 6H), 0.72 (s, 3H). 13C NMR (101 MHz, CDCl3) δ
175.4 (–CON–), 171.0 (–COO–), 125.2, 81.0, 55.4, 54.8, 48.5,
47.6, 45.6, 44.9, 42.1, 39.4, 38.7, 38.3, 37.7, 36.9, 34.3, 32.9,
30.5, 28.2, 28.1, 23.6, 23.3, 21.3, 21.2, 18.2, 17.4, 16.9, 16.7,
15.5. HR-MS (m/z) (ESI): calcd for C37H60N2O3 [M + H+]:
580.4604; found: 581.4655.
7.58 (s, 1H, –CONH–), 7.35 (d, J = 8.9 Hz, 2H), 6.82 (d, J = 8.9
Hz, 2H), 5.45 (s, 1H), 4.48 (dd, J = 10.0, 5.6 Hz, 1H), 3.76 (s,
3H), 2.03 (s, 3H), 1.12 (s, 3H), 0.97 (s, 3H), 0.91 (d, J = 6.5 Hz,
6H), 0.84 (d, J = 9.2 Hz, 6H), 0.71 (s, 3H). 13C NMR (101 MHz,
CDCl3) δ 176.0 (–CONH–), 171.0 (–COO–), 156.2, 140.2, 131.4,
125.9, 121.4, 114.1, 80.9, 55.4, 55.2, 54.3, 48.4, 47.5, 42.6,
39.9, 39.6, 39.1, 38.4, 37.7, 37.1, 36.8, 32.7, 30.9, 28.1, 27.9,
25.1, 23.5, 23.3, 21.3, 21.2, 18.1, 17.3, 16.9, 16.7, 15.6. HR-MS
(m/z) (ESI): calcd for C39H57NO4 [M + H+]: 603.4288; found:
604.4342.
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Compound 5Y10. Yield 88.9%; H NMR (400 MHz, CDCl3)
δ 7.70 (s, 1H, –CONH–), 7.44 (d, J = 7.7 Hz, 2H), 7.29 (d, J =
7.6 Hz, 2H), 7.06 (t, J = 7.4 Hz, 1H), 5.49 (s, 1H), 4.49 (dd, J =
10.2, 5.6 Hz, 1H), 2.03 (s, 3H), 1.13 (s, 3H), 0.98 (s, 3H), 0.94–
0.89 (m, 6H), 0.84 (d, J = 10.1 Hz, 6H), 0.70 (s, 3H). 13C NMR
(101 MHz, CDCl3) δ 176.3 (–CONH–), 171.0 (–COO–), 140.2,
138.2, 128.9, 126.1, 123.9, 119.7, 80.9, 55.2, 54.3, 48.6, 47.5,
42.7, 39.9, 39.6, 39.1, 38.4, 37.7, 37.1, 36.8, 32.7, 30.9, 28.1,
27.9, 25.1, 23.6, 23.5, 23.3, 21.3, 21.2, 18.1, 17.3, 16.9, 16.7,
15.6. HR-MS (m/z) (ESI): calcd for C38H55NO3 [M + H+]:
573.4182; found: 574.4242.
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Compound 5Y5. Yield 85.8%; H NMR (400 MHz, DMSO)
δ 8.73 (s, 1H, –CONH–), 7.41 (d, J = 8.3 Hz, 2H), 7.06 (d, J =
8.3 Hz, 2H), 5.30 (s, 1H), 4.40 (dd, J = 11.2, 4.5 Hz, 1H), 2.24
(s, 3H), 2.00 (s, 3H), 1.08 (s, 3H), 0.95 (d, J = 6.1 Hz, 3H),
0.89–0.85 (m, 6H), 0.80 (d, J = 4.8 Hz, 6H), 0.64 (s, 3H). 13C
NMR (101 MHz, DMSO) δ 175.4 (–CONH–), 170.5 (–COO–),
139.1, 137.2, 132.4, 129.1, 125.0, 120.9, 80.4, 55.0, 52.2, 47.9,
47.3, 42.1, 39.3, 38.8, 38.2, 37.7, 36.9, 32.9, 30.8, 28.3, 27.9,
23.9, 23.9, 23.7, 23.4, 21.5, 21.4, 20.9, 18.2, 17.6, 17.1, 15.6.
HR-MS (m/z) (ESI): calcd for C39H57NO3 [M + H+]: 587.4338;
found: 588.4392.
Cytotoxicity assay
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Compound 5Y6. Yield 82.9%; H NMR (400 MHz, CDCl3) δ
The cell lines MGC-803, Spca-2, NCI-H460, A549, T24, HepG2,
NCI-H460/DOX, HepG2/DOX and HL-7702 were obtained
from the Shanghai Cell Bank in the Chinese Academy of Sci-
ences. The MGC-803, Spca-2, NCI-H460, A549, T24, HepG2,
NCI-H460/DOX, HepG2/DOX and HL-7702 cell lines were
grown on 96-well microtitre plates at a cell density of 10 ×
105 cells per well in DMEM with 10% FBS. DMEM and FBS
7.70 (s, 1H, –CONH–), 7.32 (s, 1H), 7.17 (t, J = 8.1 Hz, 1H), 6.83
(d, J = 8.0 Hz, 1H), 6.63 (dd, J = 8.2, 1.9 Hz, 1H), 5.49 (s, 1H),
4.49 (dd, J = 10.2, 5.5 Hz, 1H), 3.79 (s, 3H), 2.04 (s, 3H), 1.13 (s,
3H), 0.98 (s, 3H), 0.94–0.89 (m, 6H), 0.84 (d, J = 9.9 Hz, 6H),
0.70 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 176.4 (–CONH–),
171.0 (–COO–), 160.1, 140.2, 139.5, 129.5, 126.1, 111.6, 110.1,
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