Molecules 2019, 24, 988
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2.24–2.10 (m, 1H), 2.76–2.58 (m, 2H), 3.13–2.98 (m, 1H), 3.38–3.24 (m, 1H), 4.77 (dd, J = 13.1, 6.1 Hz,
1H), 7.23–7.12 (m, 2H), 7.31 (d, J = 7.8 Hz, 1H), 7.45–7.38 (m, 1H), 7.62–7.54 (m, 1H), 7.85 (d, J = 7.5 Hz
1H), 7.99 (d, J = 7.7 Hz, 1H), 8.06 (d, J = 7.7 Hz, 1H), 8.23 (s, 1H); 13C-NMR (150 MHz, CDCl3)
169.4
,
δ
(CO), 149.6 (C, Ar), 136.1 (C, Ar), 132.0 (CH, Ar), 131.9 (C, Ar), 131.8 (C, Ar), 128.1 (CH, Ar), 124.9
(C, Ar), 123.9 (CH, Ar), 122.9 (CH, Ar), 121.7 (CH, Ar), 120.0 (CH, Ar), 119.4 (CH, Ar), 113.5 (C, Ar),
111.4 (CH, Ar), 67.4 (C), 38.2 (CH2), 35.3 (CH2), 31.8 (CH2), 24.1 (CH2), 23.1 (CH2), 22.5 (CH2), 14.1
(CH3); ESI-LRMS m/z: 345 [M + H]+; ESI-HRMS m/z calcd for M + H+ 345.1961, found: 345.1966.
The characterization data is in accordance with that reported in [43].
14c-Methyl-8,9,10,14c-tetrahydroindol◦o[30,2’:3,4]pyrido[2,1-a]isoquinolin-6(5H)-one (SF8a): yellow solid
(129.8 mg, yield 86%), mp 250–251 C. 1H-NMR (400 MHz, DMSO-d6)
δ 1.89 (s, 3H), 2.72–2.60 (m,
1H), 2.84–2.73 (m, 1H), 3.02–2.89 (m, 1H), 3.62 (d, J = 19.4 Hz, 1H), 4.10 (d, J = 19.2 Hz, 1H), 4.95–4.86
(m, 1H), 7.15–7.04 (m, 3H), 7.30–7.19 (m, 2H), 7.44–7.38 (m, 2H), 7.59 (d, J = 7.6 Hz, 1H), 11.26 (s, 1H);
13C-NMR (100 MHz, DMSO-d6)
δ 169.3 (CO), 141.4 (C, Ar), 136.0 (C, Ar), 134.5 (C, Ar), 132.4 (C, Ar),
127.7 (CH, Ar), 127.1 (CH, Ar), 126.2 (C, Ar), 126.1 (CH, Ar), 124.7 (CH, Ar), 120.5 (CH, Ar), 120.2
(CH, Ar), 119.2 (CH, Ar), 111.5 (CH, Ar), 111.2 (C, Ar), 61.5 (C), 38.2 (CH2), 36.9 (CH2), 25.7 (CH3),
23.3 (CH2); ESI-LRMS m/z: 303 [M + H]+; ESI-HRMS m/z calcd for M + H+ 303.1492, found: 303.1486.
The characterization data is in accordance with that reported in [43].
14c-Benzyl-8,9,10,14c-tetrahydroindolo[3’,2’:3,4]pyrido[2,1-a]isoquinolin-6(5H)-one (SF8b): pale yellow oil
1
(66.5 mg, yield 35%). H-NMR (500 MHz, CDCl3)
δ 1.84–1.73 (m, 1H), 2.48–2.38 (m, 1H), 2.67–2.56
(m, 1H), 3.40 (d, J = 13.8 Hz, 1H), 3.96–3.76 (m, 3H), 4.79 (dd, J = 12.7, 4.3 Hz, 1H), 6.80–6.71 (m, 2H),
7.08–7.00 (m, 2H), 7.16–7.08 (m, 2H), 7.28–7.20 (m, 2H), 7.33–7.28 (m, 2H), 7.50–7.42 (m, 1H), 7.66 (d,
J = 7.9 Hz, 1H), 7.96–7.88 (m, 1H), 8.36 (s, 1H); 13C-NMR (125 MHz, CDCl3)
δ
170.6 (CO), 141.0 (C,
Ar), 136.4 (C, Ar), 136.1 (C, Ar), 135.7 (C, Ar), 132.3 (C, Ar), 130.4 (2
×
CH, Ar), 128.2 (2 CH, Ar),
×
128.0 (CH, Ar), 127.7 (CH, Ar), 127.3 (C, Ar), 126.9 (CH, Ar), 126.8 (CH, Ar), 126.0 (CH, Ar), 121.6 (CH,
Ar), 121.4 (CH, Ar), 120.5 (CH, Ar), 111.7 (CH, Ar), 109.9 (C, Ar), 66.5 (C), 45.0 (CH2), 39.1 (CH2), 38.7
(CH2), 23.3 (CH2); ESI-LRMS m/z: 379 [M + H]+; ESI-HRMS m/z calcd for M + H+ 379.1805, found:
379.1815. The characterization data is in accordance with that reported in [43].
12b-Methyl-1,5,6,12b-tetrahydropyrrolo[2’,1’:3,4]pyrazino[1,2-a]indol-3(2H)-one (SF9a): white solid (107.8
◦
1
mg, yield 90%), mp 121–122 C. H-NMR (400 MHz, DMSO-d6)
δ 1.59 (s, 3H), 2.33–2.17 (m, 2H),
2.47–2.36 (m, 1H), 2.65–2.53 (m, 1H), 3.49–3.38 (m, 1H), 3.81–3.68 (m, 1H), 4.34–4.22 (m, 2H), 6.34 (s,
1H), 7.08–7.01 (m, 1H), 7.15–7.09 (m, 1H), 7.38 (d, J = 8.1 Hz, 1H), 7.51 (d, J = 7.7 Hz, 1H); 13C-NMR
(125 MHz, DMSO-d6)
δ 172.1 (CO), 142.1 (C, Ar), 135.2 (C, Ar), 127.6 (C, Ar), 120.7 (CH, Ar), 119.9 (CH,
Ar), 119.8 (CH, Ar), 109.6 (CH, Ar), 95.5 (CH, Ar), 58.6 (C), 40.9 (CH2), 34.3 (CH2), 33.6 (CH2), 29.7
(CH2), 27.2 (CH3); ESI-LRMS m/z: 241 [M + H]+; ESI-HRMS m/z calcd for M + H+ 241.1335, found:
241.1330. The characterization data is in accordance with that reported in [43].
11,12b-Dimethyl-1,5,6,12b-tetrahydropyrrolo[2’,1’:3,4]pyrazino[1,2-a]indol-3(2H)-one (SF9b): pale yellow
1
oil (111.3 mg, yield 88%). H-NMR (300 MHz, CDCl3)
δ 1.65 (s, 3H), 2.49–2.37 (m, 3H), 2.54 (s, 3H),
2.73–2.57 (m, 1H), 3.47–3.32 (m, 1H), 3.96–3.81 (m, 1H), 4.20 (dd, J = 11.7, 4.7 Hz, 1H), 4.52 (dd, J = 13.6
,
5.1 Hz, 1H), 6.30 (s, 1H), 6.98–6.89 (m, 1H), 7.15–7.09 (m, 2H); 13C-NMR (100 MHz, CDCl3)
δ
173.2 (CO),
141.1 (C, Ar), 135.4 (C, Ar), 130.0 (C, Ar), 127.9 (C, Ar), 121.8 (CH, Ar), 120.7 (CH, Ar), 106.8 (CH, Ar),
94.8 (CH, Ar), 59.5 (C), 41.3 (CH2), 35.0 (CH2), 34.3 (CH2), 30.4 (CH2), 27.8 (CH3), 18.8 (CH3); ESI-LRMS
m/z: 255 [M + H]+; ESI-HRMS m/z calcd for M + H+ 255.1492, found: 255.1488. The characterization
data is in accordance with that reported in [45].
12b-Methyl-3-oxo-1,2,3,5,6,12b-hexahydropyrrolo[2’,1’:3,4]pyrazino[1,2-a]indole-11-carbonitrile
(SF9c):
1
yellow oil (104.3 mg, yield 79%). H-NMR (300 MHz, CDCl3)
δ
1.66 (s, 3H), 2.54–2.32 (m, 3H), 2.73–2.59
(m, 1H), 3.49–3.33 (m, 1H), 4.02–3.88 (m, 1H), 4.26 (dd, J = 11.7, 4.8 Hz, 1H), 4.56 (dd, J = 13.7, 5.2 Hz,
1H), 6.52 (s, 1H), 7.26–7.19 (m, 1H), 7.52–7.44 (m, 2H); 13C-NMR (125 MHz, CDCl3)
173.1 (CO), 144.6
(C, Ar), 135.4 (C, Ar), 129.7 (C, Ar), 125.7 (CH, Ar), 121.2 (CH, Ar), 118.7 (CN), 113.9 (CH, Ar), 102.8 (C,
δ