. 2019 Aug 29;24(17):3144. doi: 10.3390/molecules24173144

Table 5.

Characterization data of N-aryl-N’-myrtanyl acylthiourea and N-(4-arylthiazol-2-yl)-N’-myrtanylacylthiourea.

Compound	Characterization Data
4m	Light yellow solid; m.p. 85–87 °C; yield 82.4%; purity 96.4%; FT-IR v (cm⁻¹): 3635 (N–H), 3164, 3028 (C–H), 2987, 2915, 2868 (C–H), 1686 (C=O), 1563 (N–H), 1598, 1516, 1498, 1469 (C=C), 1447, 1384, 1356 (C–H), 1327, 1310, 1296 (C–N), 1238 (C–O), 1143, 1102 (C=S), 756, 685. ¹H NMR (300 MHz, CDCl₃) δ: 12.47 (s, 1H), 8.55 (s, 1H), 7.72 (d, J = 8.0 Hz, 2H), 7.44 (t, J = 7.8 Hz, 2H), 7.35–7.29 (m, 1H), 3.10–3.00 (m, 1H), 2.53–2.44 (m, 2H), 2.41 (ddd, J = 13.8, 6.9, 3.6 Hz, 1H), 2.13–1.93 (m, 4H), 1.32 (s, 3H), 1.25 (d, J = 9.7 Hz, 1H), 0.97 (s, 3H). ¹³C NMR (126 MHz, CDCl₃) δ: 178.33, 176.81, 137.66, 129.25, 128.78, 126.69, 123.95, 46.22, 43.27, 40.36, 38.75, 30.00, 27.15, 24.61, 22.03, 14.81. ESI-MS: m/z 325.1 [M + Na]⁺; 301.2 [M − H]⁻.
4n	Light yellow solid; m.p. 116–118 °C; yield 80.7%; purity 96.9%; FT-IR v (cm⁻¹): 3300 (N–H), 3141, 3002 (C–H), 2943, 2918, 2865 (C–H), 1681 (C=O), 1516 (N–H), 1576, 1467 (C=C), 1442, 1382, 1366 (C–H), 1332, 1309, 1285 (C–N), 1238 (C–O), 1159, 1122 (C=S), 744. ¹H NMR (300 MHz, CDCl₃) δ: 12.45 (s, 1H), 8.68 (s, 1H), 8.22 (d, J = 8.1 Hz, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.41 (t, J = 7.7 Hz, 1H), 7.19 (t, J = 7.7 Hz, 1H), 3.07 (d, J = 7.6 Hz, 1H), 2.52–2.41 (m, 3H), 2.13–1.92 (m, 4H), 1.32 (s, 3H), 1.27 (d, J = 7.7 Hz, 1H), 0.98 (s, 3H). ¹³C NMR (126 MHz, CDCl₃) δ: 179.20, 176.60, 136.52, 132.86, 128.13, 127.37, 118.66, 46.11, 43.37, 40.38, 38.84, 29.84, 27.18, 24.56, 21.93, 14.65. ESI-MS: m/z 403.0 [M + Na]⁺; 379.1 [M − H]⁻.
4o	Light yellow solid; m.p. 89–91 °C; yield 81.3%; purity 97.2%; FT-IR v (cm⁻¹): 3295 (N–H), 3161, 3004 (C–H), 2965, 2922, 2862 (C–H), 1687, 1657 (C=O), 1518 (N–H), 1588, 1462 (C=C), 1412, 1384 (C–H), 1327 (C–N), 1249 (C–O), 1155, 1136 (C=S), 835. ¹H NMR (300 MHz, CDCl₃) δ: 12.37 (s, 1H), 8.47 (s, 1H), 7.61 (d, J = 8.1 Hz, 2H), 7.31 (s, 1H), 7.26 (s, 1H), 3.05 (s, 1H), 2.70 (q, J = 7.5 Hz, 2H), 2.48 (dd, J = 14.1, 6.9 Hz, 2H), 2.39 (d, J = 9.8 Hz, 1H), 2.02 (dd, J = 33.3, 21.1 Hz, 5H), 1.32 (s, 3H), 1.30 (d, J = 7.5 Hz, 3H), 1.28 (s, 1H), 0.97 (s, 3H). ¹³C NMR (126 MHz, CDCl₃) δ: 178.26, 176.70, 142.94, 135.27, 128.19, 123.99, 46.21, 43.24, 40.37, 38.77, 29.96, 28.41, 27.14, 24.61, 22.02, 15.33, 14.81. ESI-MS: m/z 331.2 [M + H] ⁺; 353.2 [M + Na]⁺; 329.1 [M − H]⁻.
4p	Light yellow solid; m.p. 110–112 °C; yield 83.3%; purity 95.4%; FT-IR v (cm⁻¹): 3247, 3200 (N–H), 3017 (C–H), 2999, 2921, 2870 (C–H), 1700 (C=O), 1524 (N–H), 1612, 1596, 1466 (C=C), 1409, 1387, 1369 (C–H), 1319 (C–N), 1256 (C–O), 1160, 1122, 1103 (C=S), 1063, 1015 (C–F), 841. ¹H NMR (300 MHz, CDCl₃) δ: 12.73 (s, 1H), 8.71 (s, 1H), 7.92 (d, J = 8.2 Hz, 2H), 7.69 (d, J = 8.3 Hz, 2H), 3.07 (dd, J = 6.0, 3.1 Hz, 1H), 2.55–2.43 (m, 2H), 2.39 (t, J = 10.2 Hz, 1H), 2.12–1.93 (m, 4H), 1.32 (s, 3H), 1.25 (d, J = 9.9 Hz, 1H), 0.97 (s, 3H). ¹³C NMR (126 MHz, CDCl₃) δ: 178.50, 177.19, 140.71, 128.43, 128.17, 125.97, 124.92, 123.56, 122.75, 46.29, 43.52, 43.33, 40.34, 38.74, 30.11, 27.16, 24.60, 22.07, 14.83. ESI-MS: m/z 371.1 [M + H]⁺; 369.1 [M − H]⁻_.
4q	Light yellow solid; m.p. 108–110 °C; yield 82.1%; purity 95.8%; FT-IR v (cm⁻¹): 3406 (N–H), 3152, 3001 (C–H), 2981, 2921, 2862 (C–H), 1685 (C=O), 1519 (N–H), 1628, 1595, 1469 (C=C), 1376 (C–H), 1345, 1304 (C–N), 1253, 1238 (C–O), 1164, 1138 (C=S), 995 (C–F), 740. ¹H NMR (300 MHz, CDCl₃) δ: 11.68 (s, 1H), 8.78 (s, 1H), 7.41–7.33 (m, 1H), 7.04 (t, J = 8.5 Hz, 2H), 3.07 (d, J = 10.4 Hz, 1H), 2.48 (dt, J = 11.7, 8.0 Hz, 2H), 2.44–2.39 (m, 1H), 2.12–1.94 (m, 4H), 1.32 (s, 3H), 1.26 (d, J = 9.6 Hz, 1H), 0.98 (s, 3H). ¹³C NMR (126 MHz, CDCl₃) δ: 181.73, 176.87, 159.24, 157.22, 129.32, 115.22, 111.88, 111.77, 111.59, 46.19, 43.30, 40.38, 38.81, 29.94, 27.14, 24.59, 21.92, 14.76. ESI-MS: m/z 361.1 [M + Na]⁺; 337.1 [M − H]⁻.
4r	Light yellow solid; m.p. 92–94 °C; yield 81.9%; purity 96.0%; FT-IR v (cm⁻¹): 3638 (N–H), 3132, 3028 (C–H), 2986, 2920, 2866 (C–H), 1687 (C=O), 1524 (N–H), 1607, 1505, 1465 (C=C), 1411, 1385, 1367 C–H), 1331 (C–N), 1253 (C–O), 1215, 1151 (C=S), 1010 (C–F), 837. ¹H NMR (300 MHz, CDCl₃) δ: 12.39 (s, 1H), 8.57 (s, 1H), 7.66 (dd, J = 8.7, 4.7 Hz, 2H), 7.12 (t, J = 8.5 Hz, 2H), 3.05 (dd, J = 6.3, 3.4 Hz, 1H), 2.48 (dd, J = 16.8, 7.2 Hz, 2H), 2.43–2.36 (m, 1H), 2.11–1.97 (m, 4H), 1.32 (s, 3H), 1.25 (d, J = 9.9 Hz, 1H), 0.97 (s, 3H). ¹³C NMR (126 MHz, CDCl₃) δ: 179.16, 178.87, 176.92, 161.87, 159.91, 133.67, 126.05, 115.74, 115.56, 46.24, 43.92, 43.28, 40.35, 39.92, 38.76, 30.02, 27.15, 26.27, 24.61, 23.91, 23.56, 22.05, 20.17, 16.16, 14.83. ESI-MS: m/z 343.1 [M + Na]⁺; 319.1 [M − H]⁻.
4s	Light yellow solid; m.p. 172–174 °C; yield 9.7%; purity 90.9%; FT-IR v (cm⁻¹): 3603 (N–H), 3245, 3187, 3007 (C–H), 2942, 2917, 2870 (C–H), 1697 (C=O), 1531 (N–H), 1546, 1484 (C=C), 1449, 1412, 1386 (C–H), 1309, 1293 (C–N), 1277 (C–O), 1226, 1209, 1158, 1126 (C=S), 1062 (C–S–C), 1012 (C–F), 837. ¹H NMR (300 MHz, CDCl₃) δ: 13.75 (s, 1H), 8.49 (s, 1H), 7.87 (dd, J = 8.5, 5.4 Hz, 2H), 7.11 (dd, J = 14.3, 5.6 Hz, 3H), 3.05 (dd, J = 6.6, 3.6 Hz, 1H), 2.44 (ddd, J = 20.7, 15.9, 9.3 Hz, 3H), 2.10–1.92 (m, 4H), 1.29 (s, 3H), 1.25 (d, J = 9.8 Hz, 1H), 0.93 (s, 3H). ¹³C NMR (126 MHz, CDCl₃) δ: 176.57, 174.90, 158.50, 149.69, 127.86, 115.66, 115.49, 107.60, 46.24, 43.25, 40.33, 38.86, 29.86, 27.13, 24.55, 22.02, 14.73. ESI-MS: m/z 404.1 [M + H]⁺; 426.1 [M + Na]⁺; 402.1 [M − H]⁻.
4t	Light yellow solid; m.p. 221–223 °C; yield 8.4%; purity 93.2%; FT-IR v (cm⁻¹): 3418 (N–H), 3252, 3197 (C–H), 2942, 2921, 2870 (C–H), 1699 (C=O), 1527 (N–H), 1600, 1545, 1515, 1477 (C=C), 1446, 1412, 1385 (C–H), 1342 (N=O), 1316, 1300 (C–N), 1283 (C–O), 1209, 1166, 1127, 1107 (C=S), 1061 (C–S–C), 856,730. ¹H NMR (300 MHz, CDC₃) δ: 13.81 (s, 1H), 8.57 (s, 1H), 8.27 (d, J = 8.7 Hz, 2H), 8.04 (d, J = 8.7 Hz, 2H), 7.38 (s, 1H), 3.12–3.03 (m, 1H), 2.52–2.37 (m, 3H), 2.02 (ddd, J = 27.5, 21.0, 14.2 Hz, 4H), 1.29 (s, 3H), 1.25 (d, J = 9.8 Hz, 1H), 0.94 (s, 3H). ¹³C NMR (126 MHz, CDCl₃) δ: 176.81, 175.24, 159.03, 148.21, 147.28, 139.96, 126.62, 124.11, 111.28, 46.27, 43.24, 40.29, 38.83, 29.89, 27.12, 24.53, 22.03, 14.73. ESI-MS: m/z 453.2 [M + Na]⁺; 429.1 [M − H]⁻.