Writing and overview of the paper: all writers. 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 2 (388 mg, 79%) being a white solid. = 0.33 (Cyclohexane/EtOAc 4:6); IR (ATR) cm?1: 3270, 3063, 3027, 2935, 1652, 1585, 1510; 1H-NMR (MeOD-= 15.7 Hz, 1H), 7.32C7.17 (m, 5H), 7.12 (s, 1H), 7.03 (d, = 8.4 Hz, 1H), 6.79 (d, = 8.4 Hz, 1H), 6.40 (d, = 15.7 Hz, 1H), 3.88 (s, 3H), 3.52 (t, = 7.2 Hz, 2H), 2.86 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C18H20NO3 [M + H]+: 298.1365, found: 298.1442. The analytical data were consistent with referred to data [46] previously. (3). General treatment using 4-hydroxycinnamic acidity (272 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 3 (288 mg, 65%) being a colorless syrup. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3400, 3263, 3085, 3064, 3026, 2934, 2813, 2750, 2687, 2608, 1651, 1600, 1579, 1511; 1H-NMR (MeOD-= 8.4 Hz, 2H), 6.38 (d, = 15.7 Hz, 1H), 3.51 (t, = 7.2 Hz, 2H), 2.85 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C17H18NO2 [M + H]+: 268.1259, found: 268.1336. The analytical data were consistent with referred to data [47] previously. (4). General treatment using 3,4,5-trimethoxycinnamic acidity (395 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 4 (511 mg, 90%) being a white solid. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3305, 3087, 3062, 3030, 3005, 2967, 2933, 2862, 2835, 1653, 1615, 1581, 1536, 1506; 1H-NMR (CDCl3, 300 MHz): 7.53 (d, = 15.5 Hz, 1H), 7.36C7.22 (m, 5H), 6.71 (s, 2H), 6.22 (d, = 15.5 Hz, 1H), 5.55 (bs, 1H), 3.88 (s, 6H), 3.87 (s, 3H), 3.71C3.65 (m, 2H), 2.89 (t, = 6.8 Hz, 2H); 13C-NMR (CDCl3, 75 MHz): 165.9, 153.5, 141.1, 139.6, 138.9, 130.5, 128.9, 128.8, 126.7, 120.0, 104.9, 61.1, 56.2, 40.9, 35.7; HRMS (ESI) calcd for C20H24NO4 [M + H]+: 342.1627, found: 342.1709. (5). General treatment using cinnamic acidity (246 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 5 (330 mg, 79%) being a white solid. = 0.7 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3265, 3062, 3030, 2971, 2944, 2862, 1959, 1895, 1819, 1660, 1651, 1603, 1579, 1544; 1H-NMR (CDCl3, 300 MHz): 7.62 (d, = 15.5 Hz, 1H), 7.50C7.47 (m, 2H), 7.40C7.31 (m, 5H), 7.25C7.22 (m, 3H), 6.32 (d, = 15.5 Hz, 1H), 5.58 (bs, 1H), 3.71C3.65 (m, 2H), 2.90 (t, = 6.6, 2H); HRMS (ESI) calcd for C17H18NO [M + H]+: 252.1310, found : 252.1386. The analytical data were consistent with referred to data [48] previously. (6). General treatment using 3,4-dihydroxycinnamic acidity (300 mg, 1.66 mmol) and 2-(4-hydroxyphenyl)ethylamine (228 mg, 1.66 mmol) afforded substance 6 (358 mg, 72%) as hook yellowish solid. = 0.64 (Cyclohexane/EtOAc 1:9); IR (ATR) cm?1: 3349, 3167, 3030, 2960, 2930, 2877, 1727, 1645, 1602, 1578, 1535, 1514; 1H-NMR (DMSO-= 15.6 Hz, 1H), 7.0 (d, = 8.2 Hz, 2H), 6.93 (s, 1H), 6.82 (d, = 8.0 Hz, 1H), 6.73 (d, = 8.0 Hz, 1H), 6.67 (d, = 8.2 Hz, 2H), 6.31 (d, = 15.6 Hz, 1H), 3.34C3.28 (m, 2H), 2.63 (t, = 7.3 Hz, 2H); HRMS (ESI) calcd for C17H18NO4 [M + H]+: 300.1236, found: 300.1235. The analytical data were consistent with referred to data [49] previously. (7). General treatment using 3-methoxy-4-hydroxycinnamic acidity (322 mg, 1.66 mmol) and 4-hydroxyphenethylamine (228 mg, 1.66 mmol) afforded substance 7 (298 mg, 57%) like a white solid. = 0.22 (Cyclohexane/EtOAc 5:5); IR (ATR) cm?1: 3287, 3015, 2936, 1651, 1586, 1510; 1H-NMR (MeOD-= 16.0 Hz, 1H), 7.12 (s, 1H), 7.07C7.01 (m, 3H), 6.79 (d, = 8.1 Hz, 1H), 6.71 (d, = 8.0 Hz, 2H), 6.40 (d, = 16.0 Hz, 1H), 3.88 (s, 3H), 3.47 (t, = 6.9 Hz, 2H), 2.76 (t, = 6.9 Hz, 2H); HRMS (ESI) calcd for C18H20NO4 [M + H]+: 314.1314, found: 314.1396. The analytical data were consistent with referred to data [50] previously. (8). General treatment using 4-hydroxycinnamic acidity (272 mg, 1.66 mmol) and 4-hydroxyphenethylamine (228 mg, 1.66 mmol) afforded substance 8 (233 mg, 50%) like a white solid. = 0.30 (Cyclohexane/EtOAc 5:5); IR (ATR) cm?1: 3431, 3171, 3024, 2942, 1895, 1660, 1622, 1602, 1590, 1530, 1510; 1H-NMR (MeOD-= 8.1 Hz, 2H),.Docking and SARs research indicated the key part of caffeoyl moiety, that could penetrate in to the dynamic site of ARG-I to be able to chelate the Mn2+ cofactor and connect to the key preserved residues (Asp124, His126, His141, Asp232, Asp234, and Thr246) mixed up in catalytic site of arginase, troubling the enzymatic activity thus. (m, 2H); HRMS (ESI) calcd for C17H18NO3 [M + H]+: 284.1208, found: 284.1288. The analytical data were consistent with referred to data [45] previously. (2). General treatment using 3-methoxy-4-hydroxycinnamic acidity (322 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 2 (388 mg, 79%) like a white solid. = 0.33 (Cyclohexane/EtOAc 4:6); IR (ATR) cm?1: 3270, 3063, 3027, 2935, 1652, 1585, 1510; 1H-NMR (MeOD-= 15.7 Hz, 1H), 7.32C7.17 (m, 5H), 7.12 (s, 1H), 7.03 (d, = 8.4 Hz, 1H), 6.79 (d, = 8.4 Hz, 1H), 6.40 (d, = 15.7 Hz, 1H), 3.88 (s, 3H), 3.52 (t, = 7.2 Hz, 2H), 2.86 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C18H20NO3 [M + H]+: 298.1365, found: 298.1442. The analytical data had been consistent with previously referred to data [46]. (3). General treatment using 4-hydroxycinnamic acidity (272 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 3 (288 mg, 65%) like a colorless syrup. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3400, 3263, 3085, 3064, 3026, 2934, 2813, 2750, 2687, 2608, 1651, 1600, 1579, 1511; 1H-NMR (MeOD-= 8.4 Hz, 2H), 6.38 (d, = 15.7 Hz, 1H), 3.51 (t, = 7.2 Hz, 2H), 2.85 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C17H18NO2 [M + 10Panx H]+: 268.1259, found: 268.1336. The analytical data had been consistent with previously referred to data [47]. (4). General treatment using 3,4,5-trimethoxycinnamic acidity (395 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 4 (511 mg, 90%) like a white solid. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3305, 3087, 3062, 3030, 3005, 2967, 2933, 2862, 2835, 1653, 1615, 1581, 1536, 1506; 1H-NMR (CDCl3, 300 MHz): 7.53 (d, = 15.5 Hz, 1H), 7.36C7.22 (m, 5H), 6.71 (s, 2H), 6.22 (d, = 15.5 Hz, 1H), 5.55 (bs, 1H), 3.88 (s, 6H), 3.87 (s, 3H), 3.71C3.65 (m, 2H), 2.89 (t, = 6.8 Hz, 2H); 13C-NMR (CDCl3, 75 MHz): 165.9, 153.5, 141.1, 139.6, 138.9, 130.5, 128.9, 128.8, 126.7, 120.0, 104.9, 61.1, 56.2, 40.9, 35.7; HRMS (ESI) calcd for C20H24NO4 [M + H]+: 342.1627, found: 342.1709. (5). General treatment using cinnamic acidity (246 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 5 (330 mg, 79%) like a white solid. = 0.7 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3265, 3062, 3030, 2971, 2944, 2862, 1959, 1895, 1819, 1660, 1651, 1603, 1579, 1544; 1H-NMR (CDCl3, 300 MHz): 7.62 (d, = 15.5 Hz, 1H), 7.50C7.47 (m, 2H), 7.40C7.31 (m, 5H), 7.25C7.22 (m, 3H), 6.32 (d, = 15.5 Hz, 1H), 5.58 (bs, 1H), 3.71C3.65 (m, 2H), 2.90 (t, = 6.6, 2H); HRMS (ESI) calcd for C17H18NO [M + H]+: 252.1310, found : 252.1386. The analytical data had been consistent with previously referred to data [48]. (6). General treatment using 3,4-dihydroxycinnamic acidity (300 mg, 1.66 mmol) and 2-(4-hydroxyphenyl)ethylamine (228 mg, 1.66 mmol) afforded substance 6 (358 mg, 72%) as hook yellowish solid. = 0.64 (Cyclohexane/EtOAc 1:9); IR (ATR) cm?1: 3349, 3167, 3030, 2960, 2930, 2877, 1727, 1645, 1602, 1578, 1535, 1514; 1H-NMR (DMSO-= 15.6 Hz, 1H), 7.0 (d, = 8.2 Hz, 2H), 6.93 (s, 1H), 6.82 (d, = 8.0 Hz, 1H), 6.73 (d, = 8.0 Hz, 1H), 10Panx 6.67 (d, = 8.2 Hz, 2H), 6.31 (d, = 15.6 Hz, 1H), 3.34C3.28 (m, 2H), 2.63 (t, = 7.3 Hz, 2H); HRMS (ESI) calcd for C17H18NO4 [M + H]+: 300.1236, found: 300.1235. The analytical data had been consistent with previously referred to data [49]. (7). General treatment using 3-methoxy-4-hydroxycinnamic acidity (322 mg, 1.66 mmol) and.The analytical data were consistent with referred to data [56] previously. (17). 7.32C7.17 (m, 5H), 7.12 (s, 1H), 7.03 (d, = 8.4 Hz, 1H), 6.79 (d, = 8.4 Hz, 1H), 6.40 (d, = 15.7 Hz, 1H), 3.88 (s, 3H), 3.52 (t, = 7.2 Hz, 2H), 2.86 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C18H20NO3 [M + H]+: 298.1365, found: 298.1442. The analytical data had been consistent with previously referred to data [46]. (3). General treatment using 4-hydroxycinnamic acidity (272 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 3 (288 mg, 65%) like a colorless syrup. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3400, 3263, 3085, 3064, 3026, 2934, 2813, 2750, 2687, 2608, 1651, 1600, 1579, 1511; 1H-NMR (MeOD-= 8.4 Hz, 2H), 6.38 (d, = 15.7 Hz, 1H), 3.51 (t, = 7.2 Hz, 2H), 2.85 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C17H18NO2 [M + H]+: 268.1259, found: 268.1336. The analytical data had been consistent with previously referred to data [47]. (4). General treatment using 3,4,5-trimethoxycinnamic acidity (395 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 4 (511 mg, 90%) like a white solid. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3305, 3087, 3062, 3030, 3005, 2967, 2933, 2862, 2835, 1653, 1615, 1581, 1536, 1506; 1H-NMR (CDCl3, 300 MHz): 7.53 (d, = 15.5 Hz, 1H), 7.36C7.22 (m, 5H), 6.71 (s, 2H), 6.22 (d, = 15.5 Hz, 1H), 5.55 (bs, 1H), 3.88 (s, 6H), 3.87 (s, 3H), 3.71C3.65 (m, 2H), 2.89 (t, = 6.8 Hz, 2H); 13C-NMR (CDCl3, 75 MHz): 165.9, 153.5, 141.1, 139.6, 138.9, 130.5, 128.9, 128.8, 126.7, 120.0, 104.9, 61.1, 56.2, 40.9, 35.7; HRMS (ESI) calcd 10Panx for C20H24NO4 [M + H]+: 342.1627, found: 342.1709. (5). General treatment using cinnamic acidity (246 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 5 (330 mg, 79%) like a white solid. = 0.7 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3265, 3062, 3030, 2971, 2944, 2862, 1959, 1895, 1819, 1660, 1651, 1603, 1579, 1544; 1H-NMR (CDCl3, 300 MHz): 7.62 (d, = 15.5 Hz, 1H), 7.50C7.47 (m, 2H), 7.40C7.31 (m, 5H), 7.25C7.22 (m, 3H), 6.32 (d, = 15.5 Hz, 1H), 5.58 (bs, 1H), 3.71C3.65 (m, 2H), 2.90 (t, = 6.6, 2H); HRMS (ESI) calcd for C17H18NO [M + H]+: 252.1310, found : 252.1386. The analytical data had been consistent with previously referred to data [48]. (6). General treatment using 3,4-dihydroxycinnamic acidity (300 mg, 1.66 mmol) and 2-(4-hydroxyphenyl)ethylamine (228 mg, 1.66 mmol) afforded substance 6 (358 mg, 72%) as hook yellowish solid. = 0.64 (Cyclohexane/EtOAc 1:9); IR (ATR) cm?1: 3349, 3167, 3030, 2960, 2930, 2877, 1727, 1645, 1602, 1578, 1535, 1514; 1H-NMR (DMSO-= 15.6 Hz, 1H), 7.0 (d, = 8.2 Hz, 2H), 6.93 (s, 1H), 6.82 (d, = 8.0 Hz, 1H), 6.73 (d, = 8.0 Hz, 1H), 6.67 (d, = 8.2 Hz, 2H), 6.31 (d, = 15.6 Hz, 1H), 3.34C3.28 (m, 2H), 2.63 (t, = 7.3 Hz, 2H); HRMS (ESI) calcd for C17H18NO4 [M + H]+: 300.1236, found: 300.1235. The analytical data had been consistent with previously referred to data [49]. (7). General treatment using 3-methoxy-4-hydroxycinnamic acidity (322 mg, 1.66 mmol) and 4-hydroxyphenethylamine (228 mg, 1.66 mmol) afforded substance 7 (298 mg, 57%) like a white solid. = 0.22 (Cyclohexane/EtOAc 5:5); IR (ATR) cm?1: 3287, 3015, 2936, 1651, 1586, 1510; 1H-NMR (MeOD-=.= 0.2 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3259, 3087, 3061, 3027, 2969, 2935, 2870, 1702, 1652, 1590, 1513; 1H-NMR (Acetone-= 15.6 Hz, 1H), 7.31C7.17 (m, 6H), 7.06 (s, 1H), 6.93 (d, = 8.0 Hz, 1H), 6.83 (d, = 8.0 Hz, 1H), 6.43 (d, = 15.6 Hz, 1H), 3.57C3.50 (m, 2H), 2.90C2.82 (m, 2H); HRMS (ESI) calcd for C17H18NO3 [M + H]+: 284.1208, found: 284.1288. 1H), 6.43 (d, = 15.6 Hz, 1H), 3.57C3.50 (m, 2H), 2.90C2.82 (m, 2H); HRMS (ESI) calcd for C17H18NO3 [M + H]+: 284.1208, found: 284.1288. The analytical data had been consistent with previously referred to data [45]. (2). General treatment using 3-methoxy-4-hydroxycinnamic acidity (322 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 2 (388 mg, 79%) like a white solid. = 0.33 (Cyclohexane/EtOAc 4:6); IR (ATR) cm?1: 3270, 3063, 3027, 2935, 1652, 1585, 1510; 1H-NMR (MeOD-= 15.7 Hz, 1H), 7.32C7.17 (m, 5H), 7.12 (s, 1H), 7.03 (d, = 8.4 Hz, 1H), 6.79 (d, = 8.4 Hz, 1H), 6.40 (d, = 15.7 Hz, 1H), 3.88 (s, 3H), 3.52 (t, = 7.2 Hz, 2H), 2.86 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C18H20NO3 [M + H]+: 298.1365, found: 298.1442. The analytical data had been consistent with previously referred to data [46]. (3). General treatment using 4-hydroxycinnamic acidity (272 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 3 GGT1 (288 mg, 65%) like a colorless syrup. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3400, 3263, 3085, 3064, 3026, 2934, 2813, 2750, 2687, 2608, 1651, 1600, 1579, 1511; 1H-NMR (MeOD-= 8.4 Hz, 2H), 6.38 (d, = 15.7 Hz, 1H), 3.51 (t, = 7.2 Hz, 2H), 2.85 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C17H18NO2 [M + H]+: 268.1259, found: 268.1336. The analytical data had been consistent with previously referred to data [47]. (4). General treatment using 3,4,5-trimethoxycinnamic acidity (395 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 4 (511 mg, 90%) like a white solid. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3305, 3087, 3062, 3030, 3005, 2967, 2933, 2862, 2835, 1653, 1615, 1581, 1536, 1506; 1H-NMR (CDCl3, 300 MHz): 7.53 (d, = 15.5 Hz, 1H), 7.36C7.22 (m, 5H), 6.71 (s, 2H), 6.22 (d, = 15.5 Hz, 1H), 5.55 (bs, 1H), 3.88 (s, 6H), 3.87 (s, 3H), 3.71C3.65 (m, 2H), 2.89 (t, = 6.8 Hz, 2H); 13C-NMR (CDCl3, 75 MHz): 165.9, 153.5, 141.1, 139.6, 138.9, 130.5, 128.9, 128.8, 126.7, 120.0, 104.9, 61.1, 56.2, 40.9, 35.7; HRMS (ESI) calcd for C20H24NO4 [M + H]+: 342.1627, found: 342.1709. (5). General treatment using cinnamic acidity (246 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 5 (330 mg, 79%) like a white solid. = 0.7 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3265, 3062, 3030, 2971, 2944, 2862, 1959, 1895, 1819, 1660, 1651, 1603, 1579, 1544; 1H-NMR (CDCl3, 300 MHz): 7.62 (d, = 15.5 Hz, 1H), 7.50C7.47 (m, 2H), 7.40C7.31 (m, 5H), 7.25C7.22 (m, 3H), 6.32 (d, = 15.5 Hz, 1H), 5.58 (bs, 1H), 3.71C3.65 (m, 2H), 2.90 (t, = 6.6, 2H); HRMS (ESI) calcd for C17H18NO [M + H]+: 252.1310, found : 252.1386. The analytical data had been consistent with previously referred to data [48]. (6). General treatment using 3,4-dihydroxycinnamic acidity (300 mg, 1.66 mmol) and 2-(4-hydroxyphenyl)ethylamine (228 mg, 1.66 mmol) afforded substance 6 (358 mg, 72%) as hook yellowish solid. = 0.64 (Cyclohexane/EtOAc 1:9); IR (ATR) cm?1: 3349, 3167, 3030, 2960, 2930, 2877, 1727, 1645, 1602, 1578, 1535, 1514; 1H-NMR (DMSO-= 15.6 Hz, 1H), 7.0 (d, = 8.2 Hz, 2H), 6.93 (s, 1H), 6.82 (d, = 8.0 Hz, 1H), 6.73 (d, = 8.0 Hz, 1H), 6.67 (d, = 8.2 Hz, 2H), 6.31 (d, = 15.6 Hz, 1H), 3.34C3.28 (m, 2H), 2.63 (t, = 7.3 Hz, 2H); HRMS (ESI) calcd for C17H18NO4 [M + H]+: 300.1236, found: 300.1235. The analytical data had been consistent with previously referred to data [49]. (7). General treatment using 3-methoxy-4-hydroxycinnamic acidity (322 mg, 1.66 mmol) and 4-hydroxyphenethylamine (228 mg, 1.66 mmol) afforded substance 7 (298 mg, 57%) like a white solid. = 0.22 (Cyclohexane/EtOAc 5:5); IR (ATR) cm?1: 3287, 3015, 2936, 1651, 1586, 1510; 1H-NMR (MeOD-= 16.0 Hz, 1H), 7.12 (s, 1H), 7.07C7.01 (m, 3H), 6.79 (d, = 8.1 Hz, 1H), 6.71 (d, = 8.0 Hz, 2H), 6.40 (d, = 16.0 Hz, 1H), 3.88 (s, 3H), 3.47 (t, = 6.9 Hz, 2H), 2.76 (t, = 6.9 Hz, 2H); HRMS (ESI) calcd for C18H20NO4 [M + H]+: 314.1314, found: 314.1396. The analytical data had been consistent with previously referred to data [50]. (8). General treatment using 4-hydroxycinnamic acidity (272 mg, 1.66 mmol) and 4-hydroxyphenethylamine (228 mg, 1.66.The sort of inhibition was determined following a graphical method referred to by CornishCBowden [41]. 284.1288. The analytical data had been consistent with previously referred to data [45]. (2). General treatment using 3-methoxy-4-hydroxycinnamic acidity (322 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 2 (388 mg, 79%) like a white solid. = 0.33 (Cyclohexane/EtOAc 4:6); IR (ATR) cm?1: 3270, 3063, 3027, 2935, 1652, 1585, 1510; 1H-NMR (MeOD-= 15.7 Hz, 1H), 7.32C7.17 (m, 5H), 7.12 (s, 1H), 7.03 (d, = 8.4 Hz, 1H), 6.79 (d, = 8.4 Hz, 1H), 6.40 (d, = 15.7 Hz, 1H), 3.88 (s, 3H), 3.52 (t, = 7.2 Hz, 2H), 2.86 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C18H20NO3 [M + H]+: 298.1365, found: 298.1442. The analytical data had been consistent with previously referred to data [46]. (3). General treatment using 4-hydroxycinnamic acidity (272 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 3 (288 mg, 65%) like a colorless syrup. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3400, 3263, 3085, 3064, 3026, 2934, 2813, 2750, 2687, 2608, 1651, 1600, 1579, 1511; 1H-NMR (MeOD-= 8.4 Hz, 2H), 6.38 (d, = 15.7 Hz, 1H), 3.51 (t, = 7.2 Hz, 2H), 2.85 (t, = 7.2 Hz, 2H); HRMS (ESI) calcd for C17H18NO2 [M + H]+: 268.1259, found: 268.1336. The analytical data had been consistent with previously referred to data [47]. (4). General treatment using 3,4,5-trimethoxycinnamic acidity (395 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 4 (511 mg, 90%) like a white solid. = 0.56 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3305, 3087, 3062, 3030, 3005, 2967, 2933, 2862, 2835, 1653, 1615, 1581, 1536, 1506; 1H-NMR (CDCl3, 300 MHz): 7.53 (d, = 15.5 Hz, 1H), 7.36C7.22 (m, 5H), 6.71 (s, 2H), 6.22 (d, = 15.5 Hz, 1H), 5.55 (bs, 1H), 3.88 (s, 6H), 3.87 (s, 3H), 3.71C3.65 (m, 2H), 2.89 (t, = 6.8 Hz, 2H); 13C-NMR (CDCl3, 75 MHz): 165.9, 153.5, 141.1, 139.6, 138.9, 130.5, 128.9, 128.8, 126.7, 120.0, 104.9, 61.1, 56.2, 40.9, 35.7; HRMS (ESI) calcd for C20H24NO4 [M + H]+: 342.1627, found: 342.1709. (5). General treatment using cinnamic acidity (246 mg, 1.66 mmol) and 2-phenylethylamine (209 L, 1.66 mmol) afforded substance 5 (330 mg, 79%) like a white solid. = 0.7 (CH2Cl2/MeOH 95:5); IR (ATR) cm?1: 3265, 3062, 3030, 2971, 2944, 2862, 1959, 1895, 1819, 1660, 1651, 1603, 1579, 1544; 1H-NMR (CDCl3, 300 MHz): 7.62 (d, = 15.5 Hz, 1H), 7.50C7.47 (m, 2H), 7.40C7.31 (m, 5H), 7.25C7.22 (m, 3H), 6.32 (d, = 15.5 Hz, 1H), 5.58 (bs, 1H), 3.71C3.65 (m, 2H), 2.90 (t, = 6.6, 2H); HRMS (ESI) calcd for C17H18NO [M + H]+: 252.1310, found : 252.1386. The analytical data had been consistent with previously referred to data [48]. (6). General treatment using 3,4-dihydroxycinnamic acidity (300 mg, 1.66 mmol) and 2-(4-hydroxyphenyl)ethylamine (228 mg, 1.66 mmol) afforded substance 6 (358 mg, 72%) as hook yellowish solid. = 0.64 (Cyclohexane/EtOAc 1:9); IR (ATR) cm?1: 3349, 3167, 3030, 2960, 2930, 2877, 1727, 1645, 1602, 1578, 1535, 1514; 1H-NMR (DMSO-= 15.6 Hz, 1H), 7.0 (d, = 8.2 Hz, 2H), 6.93 (s, 1H), 6.82 (d, = 8.0 Hz, 1H), 6.73 (d, = 8.0 Hz, 1H), 6.67 (d, = 8.2 Hz, 2H), 6.31 (d, = 15.6 Hz, 1H), 3.34C3.28 (m, 2H), 2.63 (t, = 7.3 Hz, 2H); HRMS (ESI) calcd for C17H18NO4 [M + H]+: 300.1236, found: 300.1235. The analytical data had been consistent with previously referred to data [49]. (7). General treatment using 3-methoxy-4-hydroxycinnamic acidity (322 mg, 1.66 mmol) and 4-hydroxyphenethylamine (228 mg, 1.66 mmol) afforded substance 7 (298 mg, 57%) like a white solid. = 0.22 (Cyclohexane/EtOAc 5:5); IR (ATR) cm?1: 3287, 3015, 2936, 1651, 1586, 1510; 1H-NMR (MeOD-= 16.0 Hz, 1H), 7.12 (s, 1H), 7.07C7.01 (m, 3H), 6.79 (d, = 8.1 Hz, 1H), 6.71 (d, = 8.0 Hz, 2H), 6.40 (d, = 16.0 10Panx Hz, 1H), 3.88 (s, 3H), 3.47 (t, = 6.9 Hz, 2H), 2.76 (t, = 6.9 Hz, 2H); HRMS (ESI) calcd for C18H20NO4 [M + H]+: 314.1314, found: 314.1396. The analytical data had been consistent with previously referred to data [50]. (8). General treatment using 4-hydroxycinnamic acidity (272 mg, 1.66 mmol) and 4-hydroxyphenethylamine (228 mg, 1.66 mmol) afforded substance 8 (233 mg, 50%) like a white solid. = 0.30 (Cyclohexane/EtOAc 5:5); IR.
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