4.2.5 Synthesis of target compounds W1-W21
K2CO3 (13.86 mmol) and 20 mL of DMF were added to a round-bottom flask along with Intermediate 4 (4.62 mmol). Intermediate 3 (5.08 mmol) was added to the reaction mixture after 0.5 h. TLC was used to track the reaction's course for around 10 h at 77°C. TLC was used to carry out the reaction. The reaction was heated, then combined with 90 mL of distilled water and extracted with ethyl acetate. The lower liquid phase was recovered, dried, filtered, and the ethyl acetate solvent was removed after three washes with saturated brine. The resultant product was purified further by column chromatography using a volumetric ratio of petroleum ether to ethyl acetate (15:1) as eluent to obtain W1-W21 ranging from 29–77%.
1-((2-(2-chlorophenyl)quinolin-4-yl)thio)-3-(1H-indol-1-yl)propan-2-ol (W1). White solid; yield: 42%; m.p. 154.4-155.1 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.17 (d, J = 8.0 Hz, 1H, Ph-H), 8.04 (d, J = 8.2 Hz, 1H, Ph-H), 7.87–7.77 (m, 1H, Ph-H), 7.73–7.63 (m, 1H, Ph-H), 7.69–7.60 (m, 2H, Ph-H), 7.57 (s, 1H, Ph-H), 7.57–7.47 (m, 3H, Ph-H), 7.47 (d, J = 8.2 Hz, 1H, Indol-2-H), 7.35 (d, J = 3.1 Hz, 1H, Ph-H), 7.08–6.98 (m, 1H, Ph-H), 6.97 (t, J = 7.0 Hz, 1H, Ph-H), 6.37 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.68 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.44 (dd, J = 15.0, 1H, -CH2CH(OH)CH2-), 4.24 (dd, J = 15.0, 1H, -CH2CH(OH)CH2-), 4.20–4.12 (m, 1H, -CH2CH(OH)CH2-), 3.36 (dd, J = 10.0, 1H, -CH2CH(OH)CH2-), 3.21 (dd, J = 15.0, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 156.18 (s), 146.83 (s), 146.67 (s), 139.32 (s), 136.14 (s), 131.74 (s), 131.59 (s), 130.52 (s), 130.39 (s), 129.98 (s), 129.58 (s), 128.16 (s), 127.48 (s), 127.14 (s), 124.78 (s), 123.25 (s), 121.01 (s), 120.47 (s), 119.03 (s), 117.26 (s), 110.05 (s), 100.66 (s), 68.23 (s), 51.01 (s), 35.38 (s); ESI-HRMS calcd for C26H21ClN2OS [M་H]་445.11386, found 445.11359.
1-((2-(4-chlorophenyl)quinolin-4-yl)thio)-3-(1H-indol-1-yl)propan-2-ol (W2). White solid; yield: 37%; m.p. 147.5-180.3 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.27–8.22 (m, 2H, Ph-H), 8.14 (d, J = 8.0 Hz, 1H, Ph-H), 8.05 (d, J = 8.2 Hz, 1H, Ph-H), 7.84 (s, 1H, Ph-H), 7.82–7.78 (m, 1H, Ph-H), 7.66–7.60 (m, 3H, Ph-H), 7.55–7.48 (m, 2H, Ph-H), 7.40 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.05–6.96 (m, 2H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.72 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.49 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.27 (dd, J = 10.0 Hz, 1H, -CH2CH(OH)CH2-), 4.19–4.13 (m, 1H, -CH2CH(OH)CH2-), 3.53 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.34 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 154.07 (s), 148.12 (s), 146.78 (s), 137.44 (s), 136.12 (s), 134.74 (s), 130.52 (s), 130.01 (s), 129.73 (s), 129.23 (s), 128.91 (s), 128.22 (s), 126.83 (s), 125.07 (s), 123.27 (s), 120.99 (s), 120.53 (s), 119.05 (s), 113.42 (s), 110.02 (s), 100.68 (s), 68.36 (s), 51.19 (s), 35.46 (s); ESI-HRMS calcd for C26H21ClN2OS [M་H]་445.11359, found 445.11359.
1-((2-(2-fluorophenyl)quinolin-4-yl)thio)-3-(1H-indol-1-yl)propan-2-ol (W3). White solid; yield: 65%; m.p. 160.1-160.5 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.16 (d, J = 8.3 Hz, 1H, Ph-H), 8.06 (d, J = 8.2 Hz, 1H, Ph-H), 7.97–7.92 (m, 1H, Ph-H), 7.82 (t, J = 8.2 Hz, 1H, Ph-H), 7.70–7.65 (m, 2H, Ph-H), 7.61–7.55 (m, 1H, Ph-H), 7.50 (dd, J = 10.0 Hz, 2H, Ph-H), 7.44–7.38 (m, 2H, Ph-H), 7.36 (d, J = 3.2 Hz, 1H, Indol-2-H), 7.04 (t, J = 10.0 Hz, 1H, Ph-H), 6.98 (t, J = 7.4 Hz, 1H, Ph-H), 6.40 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.69 (d, J = 5.7 Hz, 1H, -CH2CH(OH)CH2-), 4.46 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.25 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.20–4.13 (m, 1H, -CH2CH(OH)CH2-), 3.44 (dd, J = 10.0 Hz, 1H, -CH2CH(OH)CH2-), 3.23 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 161.51 (s), 159.53 (s), 153.22 (s), 147.71 (s), 147.29 (s), 136.56 (s), 131.92 (d, J = 8.8 Hz), 130.87 (s), 130.43 (s), 130.01 (s), 128.58 (s), 127.99 (d, J = 12.5 Hz), 127.49 (s), 125.34 (d, 4JC−F = 3.8 Hz), 125.25 (s), 123.65 (s), 121.42 (s), 120.87 (s), 119.44 (s), 117.30 (d, 3JC−F = 6.3 Hz), 116.98 (s), 116.80 (s), 110.44 (s), 101.08 (s), 68.62 (s), 51.49 (s), 35.90 (s); 19F NMR (470 MHz, DMSO-d6) δ -116.46; ESI-HRMS calcd for C26H21FN2OS [M་H]་429.14313, found 429.14314.
1-(1H-indol-1-yl)-3-((2-(m-tolyl)quinolin-4-yl)thio)propan-2-ol (W4). White solid; yield: 54%; m.p. 119.0-119.2 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.14 (dd, J = 10 Hz, 1H, Ph-H), 8.09 (s, 1H, Ph-H), 8.06 (d, J = 8.1 Hz, 1H, Ph-H), 7.98 (d, J = 8.2 Hz, 1H, Ph-H), 7.86 (s, 1H, Ph-H), 7.81–7.77 (m, 1H, Ph-H), 7.64–7.60 (m, 1H, Ph-H), 7.55–7.50 (m, 2H, Ph-H), 7.46 (t, J = 7.7 Hz, 1H, Ph-H), 7.40 (d, J = 3.1 Hz, 1H, Ph-H), 7.34 (d, J = 7.4 Hz, 1H, Indol-2-H), 7.04–6.95 (m, 2H, Ph-H), 6.43 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.7 Hz, 1H, -CH2CH(OH)CH2-), 4.51 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.27 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.21–4.14 (m, 1H, -CH2CH(OH)CH2-), 3.53 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.34 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-), 2.46 (s, 3H,-Ph-CH3); 13C NMR (125 MHz, DMSO-d6) δ 155.52 (s), 147.66 (s), 146.91 (s), 138.69 (s), 138.09 (s), 136.13 (s), 130.47 (s), 130.35 (s), 129.99 (s), 129.72 (s), 128.81 (s), 128.21 (s), 127.99 (s), 126.57 (s), 125.04 (s), 124.73 (s), 123.26 (s), 120.99 (s), 120.51 (s), 119.05 (s), 113.79 (s), 110.01 (s), 100.65 (s), 68.38 (s), 51.18 (s), 35.49 (s), 21.34 (s); ESI-HRMS calcd for C27H24N2OS [M་H]་425.16818, found 425.16821.
1-(1H-indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol (W5). White solid; yield: 29%; m.p. 158.0-158.3 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.13 (d, J = 8.2 Hz, 3H, Ph-H), 8.04 (d, J = 7.9 Hz, 1H, Ph-H), 7.82 (s, 1H, Ph-H), 7.80–7.76 (m, 1H, Ph-H), 7.62–7.58 (m, 1H, Ph-H), 7.54 (t, J = 8.4 Hz, 2H, Ph-H), 7.40 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.38 (d, J = 8.0 Hz, 2H, Ph-H), 7.06–6.98 (m, 2H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.7 Hz, 1H, -CH2CH(OH)CH2-), 4.50 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.28 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.21–4.14 (m, 1H, -CH2CH(OH)CH2-), 3.51 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.33 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 2.41 (s, 3H,-Ph-CH3); 13C NMR (125 MHz, DMSO-d6) δ 155.27 (s), 147.60 (s), 146.91 (s), 139.51 (s), 136.14 (s), 135.87 (s), 130.32 (s), 129.92 (s), 129.73 (s), 129.51 (s), 128.22 (s), 127.38 (s), 126.42 (s), 124.95 (s), 123.23 (s), 121.03 (s), 120.53 (s), 119.06 (s), 113.38 (s), 110.04 (s), 100.68 (s), 68.39 (s), 51.21 (s), 35.48 (s), 21.08 (s); ESI-HRMS calcd for C27H24N2OS [M་H]་425.16821, found 425.16821.
1-(1H-indol-1-yl)-3-((2-(3-methoxyphenyl)quinolin-4-yl)thio)propan-2-ol (W6). White solid; yield: 58%; m.p. 117.3-118.1 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.14 (dd, J = 10 Hz, 1H, Ph-H), 8.06 (d, J = 7.3 Hz, 1H, Ph-H), 7.87 (s, 1H, Ph-H), 7.84–7.82 (m, 1H, Ph-H), 7.82–7.75 (m, 1H, Ph-H), 7.65–7.60 (m, 1H, Ph-H), 7.55–7.47 (m, 1H, Ph-H), 7.55–7.47 (m, 3H, Ph-H), 7.40 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.13–7.09 (m, 1H, Ph-H), 7.05–6.96 (m, 2H, Ph-H), 6.43 (d, J = 2.5 Hz, 1H, Indol-3-H), 5.72 (d, J = 5.7 Hz, 1H, -CH2CH(OH)CH2-), 4.50 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.27 (dd, J = 10.0 Hz, 1H, -CH2CH(OH)CH2-), 4.21–4.13 (m, 1H, -CH2CH(OH)CH2-), 3.88 (s, 3H, Ph-OCH3), 3.54 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.35 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 159.82 (s), 155.19 (s), 147.77 (s), 146.81 (s), 140.22 (s), 136.13 (s), 130.39 (s), 130.06 (s), 130.01 (s), 129.72 (s), 128.21 (s), 126.67 (s), 125.12 (s), 123.26 (s), 121.01 (s), 120.51 (s), 119.89 (s), 119.05 (s), 115.29 (s), 113.89 (s), 112.95 (s), 110.03 (s), 100.66 (s), 68.41 (s), 55.38 (s), 51.21 (s), 35.47 (s); ESI-HRMS calcd for C27H24N2O2S [M་H]་441.16312, found 441.16313.
1-(5-bromo-1H-indol-1-yl)-3-((2-phenylquinolin-4-yl)thio)propan-2-ol (W7). White solid; yield: 61%; m.p. 188.8-189.2 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.23–8.20 (m, 2H, Ph-H), 8.13 (dd, J = 10 Hz, 1H, Ph-H), 8.06 (d, J = 7.9 Hz, 1H, Ph-H), 7.85 (s, 1H, Ph-H), 7.82–7.78 (m, 1H, Ph-H), 7.73 (d, J = 2.0 Hz, 1H, Ph-H), 7.64–7.61 (m, 1H, Ph-H), 7.60–7.57 (m, 2H, Ph-H), 7.56–7.51 (m, 2H, Ph-H), 7.46 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.13 (dd, J = 5 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.50 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.28 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.18–4.11 (m, 1H, -CH2CH(OH)CH2-), 3.54 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-), 3.32 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 155.38 (s), 147.74 (s), 146.90 (s), 138.70 (s), 134.98 (s), 131.30 (s), 130.40 (s), 130.04 (s), 130.02 (s), 129.82 (s), 128.92 (s), 127.49 (s), 126.63 (s), 125.02 (s), 123.42 (s), 123.24 (s), 122.68 (s), 113.68 (s), 112.20 (s), 111.72 (s), 100.43 (s), 68.37 (s), 51.37 (s), 35.41 (s); ESI-HRMS calcd for C26H21BrN2OS [M་H]་489.06311, found 489.06307.
1-(5-bromo-1H-indol-1-yl)-3-((2-(2-chlorophenyl)quinolin-4-yl)thio)propan-2-ol (W8). White solid; yield: 75%; m.p. 145.3-145.9 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.16 (dd, J = 8.3, 1.3 Hz, 1H, Ph-H), 8.04 (d, J = 8.3 Hz, 1H, Ph-H), 7.84–7.80 (m, 1H, Ph-H), 7.70–7.66 (m, 2H, Ph-H), 7.65–7.62 (m, 2H, Ph-H), 7.56–7.51 (m, 3H, Ph-H), 7.47 (d, J = 8.7 Hz, 1H, Ph-H), 7.41 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.14 (dd, J = 10 Hz, 1H, Ph-H), 6.38 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.68 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.44 (dd, J = 10.0 Hz, 1H, -CH2CH(OH)CH2-), 4.24 (dd, J = 10.0 Hz, 1H, -CH2CH(OH)CH2-), 4.17–4.10 (m, 1H, -CH2CH(OH)CH2-), 3.41 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.19 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 156.15 (s), 146.77 (s), 146.66 (s), 139.30 (s), 134.99 (s), 131.74 (s), 131.56 (s), 131.13 (s), 130.52 (s), 130.39 (s), 129.97 (s), 127.48 (s), 127.14 (s), 124.75 (s), 123.43 (s), 123.23 (s), 122.61 (s), 117.24 (s), 112.22 (s), 111.72 (s), 100.43 (s), 68.22 (s), 51.17 (s), 35.30 (s); ESI-HRMS calcd for C26H20BrClN2OS [M་H]་523.02423, found 523.02410.
1-(5-bromo-1H-indol-1-yl)-3-((2-(4-chlorophenyl)quinolin-4-yl)thio)propan-2-ol (W9). White solid; yield: 72%; m.p. 162.8-163.3 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.25–8.21 (m, 2H, Ph-H), 8.13 (d, J = 8.2 Hz, 1H, Ph-H), 8.04 (d, J = 8.3 Hz, 1H, Ph-H), 7.82–7.78 (m, 2H, Ph-H), 7.72 (d, J = 2.0 Hz, 1H, Ph-H), 7.65–7.60 (m, 3H, Ph-H), 7.51 (d, J = 8.7 Hz, 1H, Ph-H), 7.46 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.14 (dd, J = 10 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.48 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.28 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.18–4.11 (m, 1H, -CH2CH(OH)CH2-), 3.52 (dd, J = 10.0 Hz, 1H, -CH2CH(OH)CH2-), 3.33 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 154.08 (s), 148.07 (s), 146.78 (s), 137.45 (s), 134.98 (s), 134.75 (s), 131.27 (s), 130.51 (s), 130.04 (s), 130.00 (s), 129.20 (s), 128.91 (s), 126.82 (s), 125.06 (s), 123.44 (s), 123.26 (s), 122.68 (s), 113.47 (s), 112.18 (s), 111.72 (s), 100.46 (s), 68.37 (s), 51.35 (s), 35.42 (s); ESI-HRMS calcd for C26H20BrClN2OS [M་H]་523.02423, found 523.02410.
1-(5-bromo-1H-indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol (W10). White solid; yield: 63%; m.p. 166.9-167.5 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.12–8.09 (m, 3H, Ph-H), 8.03 (d, J = 8.2 Hz, 1H, Ph-H), 7.81–7.76 (m, 2H, Ph-H), 7.73 (d, J = 2.0 Hz, 1H, Ph-H), 7.62–7.58 (m, 1H, Ph-H), 7.52 (d, J = 8.7 Hz, 1H, Ph-H), 7.46 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.38 (d, J = 8.0 Hz, 2H, Ph-H), 7.14 (dd, J = 10 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.5 Hz, 1H, -CH2CH(OH)CH2-), 4.49 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.28 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.18–4.11 (m, 1H, -CH2CH(OH)CH2-), 3.52 (dd, J = 10.0 Hz, 1H, -CH2CH(OH)CH2-), 3.30 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 2.42 (s, 3H,-Ph-CH3); 13C NMR (125 MHz, DMSO-d6) δ 155.28 (s), 147.53 (s), 146.91 (s), 139.48 (s), 135.89 (s), 134.98 (s), 131.28 (s), 130.31 (s), 130.04 (s), 129.91 (s), 129.52 (s), 127.35 (s), 126.41 (s), 124.93 (s), 123.46 (s), 123.22 (s), 122.68 (s), 113.45 (s), 112.19 (s), 111.73 (s), 100.44 (s), 68.34 (s), 51.38 (s), 35.42 (s), 21.07 (s); ESI-HRMS calcd for C27H23BrN2OS [M་H]་503.07874, found 503.07872.
1-(5-chloro-1H-indol-1-yl)-3-((2-phenylquinolin-4-yl)thio)propan-2-ol (W11). White solid; yield: 52%; m.p. 156.6-157.1 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.23–8.20 (m, 2H, Ph-H), 8.13 (dd, J = 10.0 Hz, 1H, Ph-H), 8.06 (d, J = 7.9 Hz, 1H, Ph-H), 7.85 (s, 1H, Ph-H), 7.82–7.78 (m, 1H, Ph-H), 7.64–7.61 (m, 1H, Ph-H), 7.61–7.56 (m, 3H, Ph-H), 7.56–7.52 (m, 2H, Ph-H), 7.48 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.03 (dd, J = 10.0 Hz, 1H, Ph-H), 6.44 (d, J = 3.0 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.50 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.28 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.19–4.12 (m, 1H, -CH2CH(OH)CH2-), 3.53 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 3.37 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 155.38 (s), 147.74 (s), 146.90 (s), 138.70 (s), 134.75 (s), 131.45 (s), 130.38 (s), 130.02 (s), 129.82 (s), 129.32 (s), 128.90 (s), 127.48 (s), 126.62 (s), 125.02 (s), 123.76 (s), 123.24 (s), 120.90 (s), 119.63 (s), 113.67 (s), 111.71 (s), 100.51 (s), 68.39 (s), 51.39 (s), 35.42 (s); ESI-HRMS calcd for C26H21ClN2OS [M་H]་445.11362, found 445.11359.
1-(5-chloro-1H-indol-1-yl)-3-((2-(4-(trifluoromethyl)phenyl)quinolin-4-yl)thio)propan-2-ol (W12). White solid; yield: 49%; m.p. 126.6-126.8 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.39 (d, J = 8.0 Hz, 2H, Ph-H), 8.17–8.13 (m, 1H, Ph-H), 8.08 (d, J = 8.0 Hz, 1H, Ph-H), 7.92 (d, J = 8.2 Hz, 2H, Ph-H), 7.86 (s, 1H, Ph-H), 7.85–7.80 (m, 1H, Ph-H), 7.69–7.64 (m, 1H, Ph-H), 7.57 (d, J = 2.1 Hz, 1H, Ph-H), 7.55 (d, J = 8.7 Hz, 1H, Ph-H), 7.48 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.01 (dd, J = 10.0 Hz, 1H, Ph-H), 6.44 (d, J = 2.4 Hz, 1H, Indol-3-H), 5.74 (d, J = 5.5 Hz, 1H, -CH2CH(OH)CH2-), 4.48 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.28 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.19–4.11 (m, 1H, -CH2CH(OH)CH2-), 3.55 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-), 3.32 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 154.25 (s), 148.80 (s), 147.17 (s), 142.95 (s), 135.15 (s), 131.86 (s), 131.05 (s), 130.57 (s), 129.73 (s), 128.63 (s), 127.58 (s), 126.18 (s), 125.66 (s), 125.3 (dd, 3JC−F = 4.18 Hz), 124.16 (s), 123.69 (s), 121.31 (s), 120.03 (s), 114.26 (s), 112.10 (s), 100.95 (s), 68.75 (s), 51.79 (s), 35.85 (s); 19F NMR (470 MHz, DMSO-d6) δ -60.93; ESI-HRMS calcd for C27H20ClF3N2OS [M་H]་513.10107, found 513.10097.
1-(5-chloro-1H-indol-1-yl)-3-((2-(2,4-dichlorophenyl)quinolin-4-yl)thio)propan-2-ol (W13). White solid; yield: 80%; m.p. 145.5-145.9 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.15 (d, J = 7.9 Hz, 1H, Ph-H), 8.04 (d, J = 8.2 Hz, 1H, Ph-H), 7.84–7.80 (m, 2H, Ph-H), 7.72–7.64 (m, 2H, Ph-H), 7.60 (dd, J = 10.0 Hz, 1H, Ph-H), 7.54 (d, J = 2.1 Hz, 1H, Ph-H), 7.51 (d, J = 9.3 Hz, 2H, Ph-H), 7.43 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.03 (dd, J = 10.0 Hz, 1H, Ph-H), 6.39 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.69 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.43 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.25 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.17–4.09 (m, 1H, -CH2CH(OH)CH2-), 3.35 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-), 3.18 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 155.09 (s), 147.07 (s), 146.62 (s), 138.16 (s), 134.75 (s), 134.31 (s), 132.99 (s), 132.65 (s), 131.29 (s), 130.49 (s), 129.96 (s), 129.43 (s), 129.25 (s), 127.70 (s), 127.29 (s), 124.79 (s), 123.77 (s), 123.23 (s), 120.93 (s), 119.55 (s), 117.00 (s), 111.71 (s), 100.54 (s), 68.21 (s), 51.21 (s), 35.33 (s); ESI-HRMS calcd for C26H19Cl3N2OS [M་H]་513.03613, found 513.03564.
1-(5-chloro-1H-indol-1-yl)-3-((2-(4-chlorophenyl)quinolin-4-yl)thio)propan-2-ol (W14). White solid; yield: 37%; m.p. 155.1-155.4 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.25–8.21 (m, 2H, Ph-H), 8.13 (dd, J = 10.0 Hz, 1H, Ph-H), 8.04 (d, J = 7.3 Hz, 1H, Ph-H), 7.83–7.78 (m, 2H, Ph-H), 7.65–7.61 (m, 3H, Ph-H), 7.58 (d, J = 2.1 Hz, 1H, Ph-H), 7.55 (d, J = 8.8 Hz, 1H, Ph-H), 7.47 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.03 (dd, J = 10.0 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.48 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.28 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.17–4.11 (m, 1H, -CH2CH(OH)CH2-), 3.52 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.32 (dd, J = 5.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 154.08 (s), 148.08 (s), 146.78 (s), 137.45 (s), 134.75 (s), 131.44 (s), 130.51 (s), 130.01 (s), 129.32 (s), 129.20 (s), 128.91 (s), 126.82 (s), 125.06 (s), 123.76 (s), 123.26 (s), 120.91 (s), 119.63 (s), 113.47 (s), 111.71 (s), 100.54 (s), 68.38 (s), 51.37 (s), 35.43 (s); ESI-HRMS calcd for C26H20Cl2N2OS [M་H]་479.07489, found 479.07462.
1-(5-chloro-1H-indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol (W15). White solid; yield: 67%; m.p. 166.7-167.1 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.12–8.09 (m, 3H, Ph-H), 8.03 (d, J = 7.3 Hz, 1H, Ph-H), 7.80–7.76 (m, 2H, Ph-H), 7.62–7.59 (m, 1H, Ph-H), 7.59 (d, J = 2.1 Hz, 1H, Ph-H), 7.56 (d, J = 8.8 Hz, 1H, Ph-H), 7.47 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.37 (d, J = 8.0 Hz, 2H, Ph-H), 7.03 (dd, J = 10.0 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.49 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.29 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.19–4.11 (m, 1H, -CH2CH(OH)CH2-), 3.51 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.31 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 2.41 (s, 3H,-Ph-CH3); 13C NMR (125 MHz, DMSO-d6) δ 155.30 (s), 147.54 (s), 146.92 (s), 139.49 (s), 135.90 (s), 134.76 (s), 131.43 (s), 130.31 (s), 129.91 (s), 129.51 (s), 129.32 (s), 127.35 (s), 126.41 (s), 124.94 (s), 123.77 (s), 123.22 (s), 120.94 (s), 119.64 (s), 113.47 (s), 111.71 (s), 100.53 (s), 68.38 (s), 51.40 (s), 35.44 (s), 21.06 (s); ESI-HRMS calcd for C27H23ClN2OS [M་H]་459.12927, found 459.12924.
1-(5-methoxy-1H-indol-1-yl)-3-((2-phenylquinolin-4-yl)thio)propan-2-ol (W16). White solid; yield: 33%; m.p. 166.1-166.5 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.25–8.16 (m, 2H, Ph-H), 8.13 (dd, J = 5.0 Hz, 1H, Ph-H), 8.05 (d, J = 7.3 Hz, 1H, Ph-H), 7.86–7.74 (m, 2H, Ph-H), 7.67–7.57 (m, 1H, Ph-H), 7.63–7.52 (m, 2H, Ph-H),7.58–7.49 (m, 1H, Ph-H), 7.41 (d, J = 8.9 Hz, 1H, Indol-2-H), 7.35 (d, J = 3.0 Hz, 1H, Ph-H), 7.04 (d, J = 2.5 Hz, 1H, Ph-H), 6.66 (dd, J = 10.0 Hz, 1H, Ph-H), 6.35 (dd, J = 5.0 Hz, 1H, Indol-3-H), 5.71 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.44 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.24 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.18–4.11 (m, 1H, -CH2CH(OH)CH2-), 3.72 (s, 3H, Indol-5-OCH3), 3.50 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.30 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 155.36 (s), 153.49 (s), 147.79 (s), 146.90 (s), 138.68 (s), 131.41 (s), 130.39 (s), 130.12 (s), 130.02 (s), 129.82 (s), 128.90 (s), 128.60 (s), 127.49 (s), 126.62 (s), 125.02 (s), 123.24 (s), 113.58 (s), 111.12 (s), 110.72 (s), 102.21 (s), 100.37 (s), 68.41 (s), 55.39 (s), 51.37 (s), 35.46 (s); ESI-HRMS calcd for C27H24N2O2S [M་H]་441.16327, found 441.16313.
1-(5-methoxy-1H-indol-1-yl)-3-((2-(m-tolyl)quinolin-4-yl)thio)propan-2-ol (W17). White solid; yield: 29%; m.p. 142.8-143.2 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.13 (d, J = 8.4 Hz, 1H, Ph-H), 8.09 (s, 1H, Ph-H), 8.06 (d, J = 7.9 Hz, 1H, Ph-H), 7.97 (d, J = 8.0 Hz, 1H, Ph-H), 7.83(s, 1H, Ph-H), 7.81–7.77 (m, 1H, Ph-H), 7.64–7.60 (m, 1H, Ph-H), 7.46 (t, J = 7.6 Hz, 1H, Ph-H), 7.40 (d, J = 8.9 Hz, 1H, Indol-2-H), 7.34 (d, J = 3.2 Hz, 2H, Ph-H), 7.03 (d, J = 2.4 Hz, 1H, Ph-H), 6.64 (dd, J = 10.0 Hz, 1H, Ph-H), 6.34 (dd, J = 5.0 Hz, 1H, Indol-3-H), 5.71 (d, J = 5.7 Hz, 1H, -CH2CH(OH)CH2-), 4.45 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.23 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.18–4.10 (m, 1H, -CH2CH(OH)CH2-), 3.71 (s, 3H, Indol-5-OCH3), 3.50 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.31 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 2.46 (s, 3H,-Ph-CH3); 13C NMR (125 MHz, DMSO-d6) δ 155.51 (s), 153.48 (s), 147.66 (s), 146.91 (s), 138.69 (s), 138.10 (s), 131.41 (s), 130.46 (s), 130.36 (s), 130.11 (s), 129.99 (s), 128.81 (s), 128.60 (s), 128.00 (s), 126.57 (s), 125.04 (s), 124.72 (s), 123.26 (s), 113.79 (s), 111.08 (s), 110.69 (s), 102.20 (s), 100.34 (s), 68.40 (s), 55.37 (s), 51.34 (s), 35.47 (s), 21.33 (s); ESI-HRMS calcd for C28H26N2O2S [M་H]་455.17889, found 455.17878.
1-(5-methoxy-1H-indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol (W18). White solid; yield: 56%; m.p. 143.9-144.3 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.13–8.09 (m, 3H, Ph-H), 8.03 (d, J = 8.3 Hz, 1H, Ph-H), 7.80–7.75 (m, 2H, Ph-H), 7.62–7.58 (m, 1H, Ph-H), 7.41 (d, J = 8.8 Hz, 1H, Indol-2-H), 7.39–7.33 (m, 3H, Ph-H), 7.04 (d, J = 2.4 Hz, 1H, Ph-H), 6.67 (dd, J = 10.0 Hz, 1H, Ph-H), 6.35 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.71 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.44 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.24 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.17–4.11 (m, 1H, -CH2CH(OH)CH2-), 3.72 (s, 3H, Indol-5-OCH3), 3.47 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-), 3.29 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 2.41 (s, 3H, -Ph-CH3); 13C NMR (125 MHz, DMSO-d6) δ 155.26 (s), 153.49 (s), 147.60 (s), 146.91 (s), 139.49 (s), 135.86 (s), 131.43 (s), 130.32 (s), 130.11 (s), 129.92 (s), 129.51 (s), 128.60 (s), 127.36 (s), 126.42 (s), 124.94 (s), 123.22 (s), 113.33 (s), 111.11 (s), 110.73 (s), 102.23 (s), 100.38 (s), 68.40 (s), 55.36 (s), 51.38 (s), 35.47 (s), 21.07 (s); ESI-HRMS calcd for C28H26N2O2S [M་H]་455.17883, found 455.17878.
1-((2-(4-chlorophenyl)quinolin-4-yl)thio)-3-(5-methoxy-1H-indol-1-yl)propan-2-ol (W19). White solid; yield: 77%; m.p. 159.5-159.8 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.20 (d, J = 8.3 Hz, 2H, Ph-H), 8.12 (d, J = 8.4 Hz, 1H, Ph-H), 8.04 (d, J = 8.3 Hz, 1H, Ph-H), 7.85–7.74 (m, 2H, Ph-H), 7.62 (t, J = 8.4 Hz, 3H, Ph-H), 7.39 (d, J = 8.9 Hz, 1H, Ph-H), 7.34 (d, J = 3.0 Hz, 1H, Indol-2-H), 7.03 (d, J = 2.4 Hz, 1H, Ph-H), 6.65 (dd, J = 10.0 Hz, 1H, Ph-H), 6.35 (d, J = 3.0 Hz, 1H, Indol-3-H), 5.72 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.42 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.23 (dd, J = 10.0 Hz, 1H, -CH2CH(OH)CH2-), 4.16–4.09 (m, 1H, -CH2CH(OH)CH2-), 3.72 (s, 3H, Indol-5-OCH3), 3.51 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.29 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 154.08 (s), 153.50 (s), 148.17 (s), 146.80 (s), 137.45 (s), 134.76 (s), 131.44 (s), 130.57 (s), 130.15 (s), 130.03 (s), 129.22 (s), 128.94 (s), 128.64 (s), 126.87 (s), 125.09 (s), 123.28 (s), 113.35 (s), 111.13 (s), 110.75 (s), 102.26 (s), 100.43 (s), 68.40 (s), 55.39 (s), 51.39 (s), 35.48 (s); ESI-HRMS calcd for C27H23ClN2O2S [M་H]་475.12448, found 475.12415.
1-(5-methoxy-1H-indol-1-yl)-3-((2-(3-methoxyphenyl)quinolin-4-yl)thio)propan-2-ol (W20). White solid; yield: 63%; m.p. 167.1-167.4 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.13 (d, J = 8.2 Hz, 1H, Ph-H), 8.06 (d, J = 7.8 Hz, 1H, Ph-H), 7.85–7.82 (m, 2H, Ph-H), 7.81–7.78 (m, 1H, Ph-H), 7.77–7.74 (m, 1H, Ph-H), 7.64–7.60 (m, 1H, Ph-H), 7.49 (t, J = 7.9 Hz, 1H, Ph-H), 7.40 (d, J = 8.9 Hz, 1H, Indol-2-H), 7.34 (d, J = 3.1 Hz, 1H, Ph-H), 7.12 (dd, J = 10.0 Hz, 1H, Ph-H), 7.03 (d, J = 2.5 Hz, 1H, Ph-H), 6.65 (dd, J = 10.0 Hz, 1H, Ph-H), 6.34 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.70 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.44 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.23 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.19–4.10 (m, 1H, -CH2CH(OH)CH2-), 3.88 (s, 3H, -Ph-OCH3), 3.71(s, 3H, Indol-5-OCH3), 3.51 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-), 3.34–3.29 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 159.83 (s), 155.18 (s), 153.49 (s), 147.77 (s), 146.82 (s), 140.22 (s), 131.41 (s), 130.39 (s), 130.11 (s), 130.05 (s), 130.00 (s), 128.60 (s), 126.67 (s), 125.12 (s), 123.26 (s), 119.89 (s), 115.28 (s), 113.88 (s), 112.96 (s), 111.08 (s), 110.71 (s), 102.23 (s), 100.34 (s), 68.44 (s), 55.38 (s), 51.37 (s), 35.45 (s); ESI-HRMS calcd for C28H26N2O3S [M་H]་471.17404, found 471.17369.
1-(5-methoxy-1H-indol-1-yl)-3-((2-(4-(trifluoromethyl)phenyl)quinolin-4-yl)thio)propan-2-ol (W21). White solid; yield: 69%; m.p. 152.9-153.3 ˚С; 1H NMR (500 MHz, DMSO-d6) δ 8.36 (d, J = 8.0 Hz, 2H, Ph-H), 8.14 (dd, J = 5.0 Hz, 1H, Ph-H), 8.07 (d, J = 8.4 Hz, 1H, Ph-H), 7.91 (d, J = 8.2 Hz, 2H, Ph-H), 7.83–7.79 (m, 2H, Ph-H), 7.67–7.63 (m, 1H, Ph-H), 7.40 (d, J = 8.9 Hz, 1H, Indol-2-H), 7.35 (d, J = 3.0 Hz, 1H, Ph-H), 7.03 (d, J = 2.4 Hz, 1H, Ph-H), 6.65 (dd, J = 10.0 Hz, 1H, Ph-H), 6.35 (d, J = 3.5 Hz, 1H, Indol-3-H), 5.72 (d, J = 5.6 Hz, 1H, -CH2CH(OH)CH2-), 4.43 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.25 (dd, J = 15.0 Hz, 1H, -CH2CH(OH)CH2-), 4.19–4.11 (m, 1H, -CH2CH(OH)CH2-), 3.71(s, 3H, Indol-5-OCH3), 3.49 (dd, J = 15.0 Hz, 1H,-CH2CH(OH)CH2-), 3.30 (dd, J = 10.0 Hz, 1H,-CH2CH(OH)CH2-); 13C NMR (125 MHz, DMSO-d6) δ 153.78 (s), 153.49 (s), 148.46 (s), 146.77 (s), 142.49 (s), 131.44 (s), 130.65 (s), 130.14 (s), 129.5 (dd, 1JC−F = 252.0 Hz), 128.63 (s), 128.20 (s), 127.18 (s), 125.7 (dd, 3JC−F = 7.5 Hz), 125.50 (s), 125.26 (s), 123.29 (s), 113.69 (s), 111.10 (s), 110.73 (s), 102.23 (s), 100.43 (s), 68.40 (s), 55.33 (s), 51.38 (s), 35.51 (s); ESI-HRMS calcd for C28H23F3N2O2S [M་H]་509.15109, found 509.15051.