## 2 Materials and Methods
### Synthesis of Chalcone Derivatives
\({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)) \(\delta\): 12.90 (s, 1H, OH), 7.94 (dd, \(J_{1}\) = 8.1, \(J_{2}\) = 1.6 Hz, 1H, H2\({}^{\prime}\)), 7.93 (d, \(J\) = 15.2 Hz, 1H, H7), 7.52 (d, \(J\) = 15.6 Hz, 1H, H8), 7.51 (ddd, \(J_{1}\) = 8.4, \(J_{2}\) = 8.4, \(J_{3}\) = 1.6 Hz, 1H, H4\({}^{\prime}\)), 7.14-6.93 (m, 5H, H2, H3, H6, H3\({}^{\prime}\), H5\({}^{\prime}\)), 3.97 (s, 3H, H10).\({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)) \(\delta\): 193.6 (s, C9), 163.5 (s, C6\({}^{\prime}\)), 148.7 (s, C3), 146.9 (s, C4), 145.8 (d, C7), 136.1 (d, C4\({}^{\prime}\)), 129.5 (d, C2\({}^{\prime}\)), 127.4 (s, C1), 123.7 (d, C6), 121.6 (d, C3\({}^{\prime}\)), 120.9 (s, C1\({}^{\prime}\)), 118.7 (d, C8), 118.1 (d, C5\({}^{\prime}\)), 117.6 (d, C5), 110.3 (d, C2), 56.1 (q, C10). GC-MS m/z (rel. int.) = 270.25 [M]\({}^{+}\) (4), 150.19 (28), 135.16 (29), 121.15 (16), 120.15 (26), 107.16 (33), 92.11 (100), 77.15 (68),1337 (N-O), cm\({}^{-1}\). \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)) 8: 12.44 (s, 1H, OH), 8.81 (d, \(J\) = 2.7 Hz, 1H, H6), 8.28 (dd, \(J\) = 8.4, \(J_{2}\) = 1.3 Hz, 1H, H4), 8.196 (d, \(J\) = 15.5 Hz, 1H, H7), 8.192 (dd, \(J_{1}\) = 9.2, \(J_{2}\) = 2.8 Hz, 1H, H2\({}^{\prime}\)), 8.10 (d, \(J\) = 15.7 Hz, 1H, H8), 7.60 (dd, \(J_{1}\) = 7.4, \(J_{2}\) = 1.4 Hz, 1H, H4\({}^{\prime}\)), 7.13 (d, \(J\) = 9.1 Hz, 1H, H3\({}^{\prime}\)), 7.04 (dd, \(J_{1}\) = 7.8, \(J_{2}\) = 1.0 Hz, 1H, H5\({}^{\prime}\)), 7.03 (d, \(J\) = 7.8 Hz, 1H, H3). \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)) 8: 193.5 (s, C9), 162.8 (s, C2), 161.8 (s, C6\({}^{\prime}\)), 140.0 (s, C5), 137.4 (d, C7), 136.2 (d, C4\({}^{\prime}\)), 130.9 (d, C2\({}^{\prime}\)), 127.3 (d, C4, C6), 124.5 (d, C3\({}^{\prime}\)), 123.2 (s, C1\({}^{\prime}\)), 121.7 (d, C8), 119.0 (d, C5\({}^{\prime}\)), 117.6 (s, C1), 116.6 (d, C3). GC-MS m/z (rel. int.) = 285.15 [M]\({}^{+}\) (1), 253.64 (1), 220.22 (a), 191.54 (3), 171.27 (6), 149.28 (6), 137.01 (16), 117.17 (18), 84.18 (51), 73.10 (32), 69.20 (41), 63.11 (49), 61.14 (41), 30.16 (100). (\(E\))-1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (**2e**): Yellow crystals (yield 40%). C\({}_{16}\)H\({}_{14}\)O\({}_{3}\). Mp = 76-78 \({}^{\circ}\)C. IR (ATR diamond, cm\({}^{-1}\)) = 3082 (C-H), 2963 (C-H), 1685 (C=O), 1255 (C-O) cm\({}^{-1}\). \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)) \(\delta\): 12.91 (s, 1H, OH), 7.919 (dd, \(J_{1}\) = 8.0, \(J_{2}\) = 1.7 Hz, 1H, H2\({}^{\prime}\)), 7.911 (d, \(J\) = 15.0 Hz, 1H, H7), 7.62 (dd, \(J_{1}\) = 8.8, \(J_{2}\) = 1.7 Hz, 1H, H2), 7.60 (dd, \(J_{1}\) = 8.5, \(J_{2}\) = 1.7 Hz, 1H, H6), 7.54 (d, \(J\) = 15.0 Hz, 1H, H8), 7.49 (ddd, \(J_{1}\) = 8.6, \(J_{2}\) = 8.5, \(J_{3}\) = 1.5 Hz, 1H, H4\({}^{\prime}\)), 7.02 (dd, \(J_{1}\) = 8.4, \(J_{2}\) = 1.0 Hz, 1H, H5\({}^{\prime}\)), 6.95 (ddd, \(J_{1}\) = 8.8, \(J_{2}\) = 2.0 Hz, 2H, H3, H5), 6.94 (ddd, \(J_{1}\) = 9.6, \(J_{2}\) = 10.9, \(J_{3}\) = 1.2 Hz, 1H, H3\({}^{\prime}\)), 3.85 (s, 3H, H10). \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)) \(\delta\): 193.8 (s, C9), 163.7 (s, C6\({}^{\prime}\)), 162.1 (s, C4), 145.4 (d, C7), 136.2 (s, C4\({}^{\prime}\)),130.6 (d, C2, C6), 129.6 (d, C2\({}^{\prime}\)), 127.5 (s, C1), 120.2 (s, C1\({}^{\prime}\)), 118.8 (d, C5\({}^{\prime}\)), 118.7 (d, C3\({}^{\prime}\)), 117.7 (d, C8), 114.6 (d, C3, C5), 55.5 (q, C10). GC-MS m/z (rel. int.) = 254.19 [M]\({}^{+}\) (17), 253.20 (12), 134.12 (100), 121.11 (34), 119.12 (40), 92.07 (79), 65.08 (84), 63.07 (90). (\(E\))-1-(2-hydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one (**2f**): Orangish yellow crystals (yield 40%). C\({}_{16}\)H\({}_{14}\)O\({}_{3}\). Mp = 86-90 \({}^{\circ}\)C. IR (ATR diamond, cm\({}^{-1}\)) = 3081 (C-H), 2918 (C-H), 1636 (C=O), 1253 (C-O) cm\({}^{-1}\).