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23.5 (CH2), 22.8 (CH2), 14.3 (CH3); IR (ATR): νmax 3382, 3329, 3173, 2918, 2850, 1683, 1664,
1630, 1560, 1519, 1479, 1452, 1392, 1366, 1339, 1315, 1283, 1249, 1198, 1170, 1147, 1066, 1039,
1012, 988, 916, 889, 860, 823, 776, 719, 708, 659 cm−1; HRMS (+ESI): Found m/z 654.2187
[M+Na]+, C28H46BrN3O6SNa required 654.2183.
tert-Butyl (3-(2-(4-(dodecylsulfonamido)-[1,10-biphenyl]-3-yl)-2-oxoacetamido)propyl)
carbamate (25c)
The titled compound was synthesised from 1-(dodecylsulfonyl)-5-phenylindoline-2,3-
dione 8c (0.32 g, 0.71 mmol) and N-Boc-1,3-propandiamine (0.13 g, 0.71 mmol) following
general synthetic procedure E. The product was obtained as a yellow solid (0.39 g, 88%);
mp 120.8–121.0 ◦C; 1H NMR (400 MHz, CDCl3):
δ 10.48 (s, 1H, NH), 8.75 (s, 1H, ArH),
7.89–7.79 (m, 2H, ArH), 7.71 (bs, 1H, NH), 7.60–7.53 (m, 2H, ArH), 7.48–7.41 (m, 2H, ArH),
7.39–7.33 (m, 1H, ArH), 4.81 (bs, 1H, NH), 3.48 (q, J = 6.3 Hz, 2H, CH2), 3.29–3.14 (m, 4H,
CH2), 1.87–1.71 (m, 4H, CH2), 1.44 (s, 9H, CH3), 1.43–1.17 (m, 18H, CH2), 0.87 (t, J = 7.1 Hz,
3H, CH3); 13C NMR (100 MHz, CDCl3):
δ 191.5 (CO), 162.9 (CO), 156.9 (CO), 141.1 (ArC),
139.1 (ArC), 135.7 (ArC), 135.1 (ArCH), 133.6 (ArCH), 129.2 (ArCH), 127.9 (ArCH), 126.9
(ArCH), 119.3 (ArC), 118.5 (ArCH), 79.9 (C), 52.8 (CH2), 37.3 (CH2), 36.4 (CH2), 32.0 (CH2),
30.2 (CH2), 29.7 (CH2), 29.7 (CH2), 29.6 (CH2), 29.4 (CH2), 29.4 (CH2), 29.1 (CH2), 28.5
(CH3), 28.2 (CH2), 23.5 (CH2), 22.8 (CH2), 14.2 (CH3); IR (ATR): νmax 3351, 3308, 2922, 2851,
1683, 1666, 1644, 1582, 1518, 1483, 1443, 1386, 1364, 1347, 1325, 1294, 1247, 1196, 1155, 1070,
1040, 1011, 977, 906, 895, 882, 864, 850, 804, 776, 758, 740, 716, 684 cm−1; HRMS (+ESI):
Found m/z 652.3394 [M+Na]+, C34H51N3O6SNa required 652.3391.
tert-Butyl (3-(2-(2-(hexadecylsulfonamido)phenyl)-2-oxoacetamido)propyl)carbamate (26a
)
The titled compound was synthesised from 1-(hexadecylsulfonyl)indoline-2,3-dione
9a (0.21 g, 0.47 mmol) and N-Boc-1,3-propandiamine (85 mg, 0.47 mmol) following general
synthetic◦procedure E. The product was obtained as a yellow solid (0.28 g, 97%); mp
δ 10.50 (s, 1H, NH), 8.45 (d, J = 7.9 Hz, 1H, ArH),
86.7–90.1 C; 1H NMR (400 MHz, CDCl3):
7.77 (d, J = 8.4 Hz, 1H, ArH), 7.68–7.56 (m, 2H, NH, ArH), 7.19–7.11 (m, 1H, ArH), 4.84 (bs,
1H, NH), 3.47 (q, J = 6.5 Hz, 2H, CH2), 3.29–3.11 (m, 4H, CH2), 1.85–1.69 (m, 4H, CH2), 1.44
(s, 9H, CH3), 1.40–1.16 (m, 26H, CH2), 0.87 (t, J = 7.0 Hz, 3H, CH3); 13C NMR (150 MHz,
CDCl3):
δ 191.7 (CO), 163.1 (CO), 156.9 (CO), 142.1 (ArC), 136.7 (ArCH), 135.3 (ArCH),
122.6 (ArCH), 118.8 (ArC), 118.0 (ArCH), 79.9 (C), 52.7 (CH2), 37.3 (CH2), 36.4 (CH2), 32.1
(CH2), 30.2 (CH2), 29.8 (CH2), 29.8 (CH2), 29.8 (CH2), 29.8 (CH2), 29.8 (CH2), 29.7 (CH2),
29.6 (CH2), 29.5 (CH2), 29.4 (CH2), 29.1 (CH2), 28.5 (CH3), 28.2 (CH2), 23.5 (CH2), 22.8
(CH2), 14.3 (CH3); IR (ATR): νmax 3362, 3253, 2916, 2849, 2113, 1684, 1637, 1602, 1571, 1523,
1467, 1391, 1335, 1247, 1220, 1152, 1077, 1057, 1006, 918, 818, 753, 671 cm−1; HRMS (+ESI):
Found m/z 632.3703 [M+Na]+, C32H55N3O6SNa required 632.3704.
tert-Butyl (3-(2-(5-bromo-2-(hexadecylsulfonamido)phenyl)-2-oxoacetamido)propyl)
carbamate (26b)
The titled compound was synthesised from 5-bromo-1-(hexadecylsulfonyl)indoline-
2,3-dione 9b (0.33 g, 0.64 mmol) and N-Boc-1,3-propandiamine (0.12 g, 0.65 mmol) follow-
ing general synthetic procedure E. The product was obtained as a yellow solid (0.41 g,
91%); mp 81.7–83.1 ◦C; 1H NMR (400 MHz, CDCl3):
δ 10.38 (s, 1H, NH), 8.66 (s, 1H, ArH),
7.76 (bs, 1H, NH), 7.73–7.64 (m, 2H, NH, ArH), 4.80 (bs, 1H, NH), 3.46 (q, J = 6.5 Hz, 2H,
CH2), 3.28–3.19 (m, 2H, CH2), 3.17–3.10 (m, 2H, CH2), 1.83–1.70 (m, 4H, CH2), 1.45 (s, 9H,
CH3), 1.41–1.17 (m, 26H, CH2), 0.87 (t, J = 7.1 Hz, 3H, CH3); 13C NMR (100 MHz, CDCl3):
δ
190.4 (CO), 162.2 (CO), 157.0 (CO), 141.0 (ArC), 139.3 (ArCH), 137.4 (ArCH), 120.4 (ArC),
119.8 (ArCH), 115.2 (ArC), 80.0 (C), 52.9 (CH2), 37.2 (CH2), 36.4 (CH2), 32.1 (CH2), 30.2
(CH2), 29.8 (CH2), 29.8 (CH2), 29.8 (CH2), 29.8 (CH2), 29.8 (CH2), 29.7 (CH2), 29.6 (CH2),
29.5 (CH2), 29.4 (CH2), 29.1 (CH2), 28.5 (CH3), 28.2 (CH2), 23.5 (CH2), 22.8 (CH2), 14.3
(CH3); IR (ATR): νmax 3370, 3184, 3113, 2918, 2850, 1685, 1635, 1519, 1479, 1389, 1335,