# Trimethoxycinnamates and Their Cholinesterase Inhibitory Activity
## 2 Materials and Methods
### Synthesis
Yield 52%; Mp 117-119 \({}^{\circ}\)C; IR (ATR, cm\({}^{-1}\)): 3068, 3008, 2971, 2944, 2846, 1727, 1711, 1635, 1581, 1501, 1471, 1448, 1419, 1338, 1322, 1274, 1237, 1224, 1183, 1149, 1120, 1092, 1042, 1012, 999, 986, 943, 926, 848, 834, 824, 797, 785, 761, 746, 707, 657, 635, 520, 604, 529, 519, 458; \({}^{1}\)H-NMR (DMSO-\(d_{6}\)), \(\delta\): 7.80 (d, \(J\) = 15.8 Hz, 1H), 7.30-7.25 (m, 4H) 7.18 (s, 2H), 6.91 (d, \(J\) = 15.8 Hz, 1H), 3.84 (s, 6H), 3.71 (s, 3H), 3.13 (s, 3H); \({}^{13}\)C-NMR (DMSO-\(d_{6}\)), \(\delta\): 165.1, 159.6 (d, \(J\) = 241.3 Hz), 153.1, 146.9, 146.6 (d, \(J\) = 2.9 Hz), 139.9, 129.4, 123.6 (d, \(J\) = 8.7 Hz), 116.1 (d, \(J\) = 4.3 Hz), 116.0, 106.3, 60.1, 56.1; HR-MS: C\({}_{18}\)H\({}_{18}\)FO\({}_{5}\) [M + H]\({}^{+}\) calculated 333.1133 _m/z_, found 333.1133 _m/z_. _4-Bromphenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate_ **(5)**. Yield 45%; Mp 112-114 \({}^{\circ}\)C; IR (ATR, cm\({}^{-1}\)) 3090, 3063, 3005, 2970, 2944, 2837, 1710, 1629, 1581, 1505, 1483, 1462, 1451, 1433, 1419, 1340, 1322, 1271, 1245, 1188, 1155, 1123, 1065, 1042, 1009, 998, 945, 924, 916, 876, 858, 846, 839, 827, 821, 802, 782, 765, 751, 715, 673, 656, 644, 628, 601, 584, 523, 499, '1H-NMR (DMSO-\(d_{6}\)), \(\delta\): 7.81 (d, \(J\) = 15.8 Hz, 1H), 7.65-7.62 (m, 2H), 7.22-7.22-Fluorophenol (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate (**6**). Yield 60%; Mp 165-167 \({}^{\circ}\)C; IR (ATR, cm\({}^{-1}\)): 3044, 3010, 2963, 2942, 2837, 1717, 1628, 1580, 1508, 1498, 1466, 1454, 1437, 1419, 1337, 1322, 1273, 1244, 1225, 1190, 1176, 1168, 1156, 1122, 1097, 1030, 998, 975, 951, 925, 916, 873, 849, 834, 827, 800, 785, 756, 226, 702, 640, 604, 574, 552, 543, 528, 491, 469; \({}^{1}\)H-NMR (DMSO-\(d_{6}\)), 8: 7.85 (d, \(J\) = 16.5 Hz, 1H), 7.42-7.33 (m, 3H), 7.28 (td, \(J\) = 7.6 Hz, \(J\) = 1.4 Hz, 1H), 7.20 (s, 2H), 6.97 (d, \(J\) = 15.8 Hz, 1H), 3.84 (s, 6H), 3.72 (s, 3H); \({}^{13}\)C-NMR (DMSO-\(d_{6}\)), 8: 164.4, 153.9 (d, \(J\) = 245.7 Hz), 153.4, 147.9, 140.2, 137.9 (d, \(J\) = 13.0 Hz), 129.5, 127.8 (d, \(J\) = 7.2 Hz), 125.4 (d, \(J\) = 4.3 Hz), 124.5, 116.9 (d, \(J\) = 18.8 Hz), 115.5, 106.6, 60.4, 56.32; HR-MS: C\({}_{18}\)H\({}_{18}\)FO\({}_{5}\) [M + H]\({}^{+}\) calculated 333.1133 \(m/z\), found 333.1129 \(m/z\). 2-Chlorophenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate (**7**). Yield 59%; Mp 104-107 \({}^{\circ}\)C; IR (ATR, cm\({}^{-1}\)): 2999, 2965, 2942, 2837, 1720, 1630, 1578, 1506, 1476, 1466, 1449, 1437, 1415, 1335, 1319, 1298, 1273, 1240, 1198, 1187, 1148, 1123, 1055, 1029, 996, 971, 951, 923, 914, 872, 841, 829, 816, 787, 762, 750, 739, 715, 683, 661, 637, 602, 563, 527, 796, 450; \({}^{1}\)H-NMR (DMSO-\(d_{6}\)), 8: 7.86 (d, \(J\) = 15.8 Hz, 1H), 7.61 (dd, \(J\) = 8.2 Hz, \(J\) = 1.4 Hz, 1H), 7.44 (td, \(J\) = 7.6 Hz, \(J\) = 1.4 Hz, 1H), 7.39 (dd, \(J\) = 8.2 Hz, \(J\) = 2.1 Hz, 1H), 7.34 (td, \(J\) = 7.6 Hz, \(J\) = 1.4 Hz, 1H), 7.21 (s, 2H), 6.99 (d, \(J\) = 15.8 Hz, 1H), 3.84 (s, 6H), 3.82 (s, 3H); \({}^{13}\)C-NMR (DMSO-\(d_{6}\)), 8: 164.2, 153.1, 147.6, 146.7, 140.0, 130.1, 129.3, 128.5, 127.6, 126.0, 124.4, 115.5, 106.5, 60.1, 56.1; HR-MS: C\({}_{18}\)H\({}_{18}\)ClO\({}_{5}\) [M + H]\({}^{+}\) calculated 349.0837 \(m/z\), found 349.0837 \(m/z\). 2,6-Dimethoxyphenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate (**8**). Yield 69%; Mp 155-157 \({}^{\circ}\)C; IR (ATR, cm\({}^{-1}\)): 3008, 2942, 2838, 1720, 1631, 1606, 1582, 1505, 1495, 1480, 1454, 1443, 1432, 1418, 1340, 1299, 1272, 1258, 1244, 1193, 1174, 1138, 1108, 1028, 1004, 982, 927, 866, 842, 822, 812, 773, 755, 714, 637, 629, 602, 554, 525, 507, 459; \({}^{1}\)H-NMR (DMSO-\(d_{6}\)), 8: 7.75 (d, \(J\) = 16.5 Hz, 1H), 7.19 (t, \(J\) = 8.2 Hz, 1H), 7.18 (s, 2H), 6.92 (d, \(J\) = 15.8 Hz, 1H), 6.77 (d, \(J\) = 8.2 Hz, 2H), 3.84 (s, 6H), 3.76 (s, 6H), 3.71 (s, 3H); \({}^{13}\)C-NMR (DMSO-\(d_{6}\)), 8: 164.1, 153.1, 152.1, 146.5, 139.7, 129.5, 128.0, 126.3, 116.3, 106.3, 105.0, 60.1, 56.1, 55.9; HR-MS: C\({}_{20}\)H\({}_{23}\)O\({}_{7}\) [M + H]\({}^{+}\) calculated 375.1438 \(m/z\), found 375.1433 \(m/z\).