## 2 Materials and Methods
### Chemistry
), 2957, (CH, aliph. ), 1660 (C=O), 1603 (C=N); \({}^{1}\)H NMR (600 MHz, DMSO-\(d_{6}\)): 3.62 (s, 2H, CH\({}_{2}\)), 7.27-7.28 (m, 1H, ArH), 7.32-7.34 (m, 4H, ArH), 7.80-7.81 (m, 2H, ArH), 8.33 (s, 1H, =CH), 12.26 (s, 1H, OH), 12.51 (s, 1H, NH); \({}^{13}\)C NMR (150 MHz, DMSO-\(d_{6}\)): 41.19 (CH\({}_{2}\)), 110.82, 111.59, 121.38, 127.23, 128.87, 129.62, 132.56, 135.94, 141.17 (11C\({}_{\rm{ar}}\)), 146.51 (=CH), 153.99 (C\({}_{\rm{ar}}\)), 167.26 (C=O). \(N^{\prime}\)-[(_E_)-(5-chloro-2-hydroxyphenyl)methylidene]-2-phenylacetohydrazide (**4**)  
Color: white; M.p. : 194 \({}^{\circ}\)C; yield: 52%; for C\({}_{15}\)H\({}_{13}\)ClN\({}_{2}\)O\({}_{2}\) (288.73) calculated: C: 62.40%, H: 4.54%, N: 9.70%; found: C: 62.50%, H: 4.55%, N: 9.67%. IR (cm\({}^{-1}\)): 3625 (OH), 3189 (NH), 3067 (CH, arom. ), 2970 (CH, aliph. ), 1664 (C=O), 1603 (C=N); \({}^{1}\)H NMR (600 MHz, DMSO-\(d_{6}\)): 3.57 (s, 2H, CH\({}_{2}\)), 6.92 (t, 2H, ArH, \(J\) = 6 Hz, \(J\) = 12 Hz), 7.22-7.27 (m, 1H, ArH), 7.29-7.35 (m, 2H, ArH), 7.62 (d, 1H, ArH, \(J\) = 6 Hz), 7.68 (d, 1H, ArH, \(J\) = 6 Hz), 8.24 (s, 1H, ArH), 8.39 (s, 1H, =CH), 11.43 (s, 1H, OH), 11.93 (s, 1H, NH); \({}^{13}\)C NMR (150 MHz, DMSO-\(d_{6}\)): 41.44 (CH\({}_{2}\)), 118.63, 121.07, 127.15, 128.83, 129.57, 131.15, 135.84, 139.0 (10C\({}_{\rm{ar}}\)), 145.11 (=CH), 155.53, 156.36 (2C\({}_{\rm{ar}}\)), 167.03 (C=O). \(N^{\prime}\)-[(_E_)-(3,5-dichloro-2-hydroxyphenyl)methylidene]-2-phenylacetohydrazide (**5**)  
Color: white; M.p. : 282 \({}^{\circ}\)C; yield: 94%; for C\({}_{15}\)H\({}_{12}\)Cl\({}_{2}\)N\({}_{2}\)O\({}_{2}\) (323.17) calculated: C: 55.75%, H: 3.74%, N: 8.67%; found: C: 55.56%, H: 3.75%, N: 8.69%. IR (cm\({}^{-1}\)): 3625 (OH), 3182 (NH), 3070 (CH, arom. ), 2950 (CH, aliph. ), 1660 (C=O), 1595 (C=N); \({}^{1}\)H NMR (600 MHz, DMSO-\(d_{6}\)): 3.62 (s, 2H, CH\({}_{2}\)), 7.22-7.30 (m, 2H, ArH), 7.32-7.36 (m, 2H, ArH), 7.58-7.60 (m, 1H, ArH), 7.64-7.66 (m, 1H, ArH), 8.25 (s, 1H, ArH), 8.36 (s, 1H, =CH), 11.63 (s, 1H, OH), 11.63 (s, 1H, OH), 12.23 (s, 1H, NH). \({}^{13}\)C NMR (150 MHz, DMSO-\(d_{6}\)): 41.23 (CH\({}_{2}\)), 121.18, 121.87, 123.35, 127.23, 128.87, 129.62, 130.64, 135.56, 140.28 (11C\({}_{\rm{ar}}\)), 146.41 (=CH), 152.59 (C\({}_{\rm{ar}}\)) 167.26 (C=O). \(N^{\prime}\)-[(_E_)-(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-2-phenylacetohydrazide (**6**)  
Color: white; M.p. : 210-212 \({}^{\circ}\)C; yield: 76%; for C\({}_{15}\)H\({}_{12}\)Br\({}_{\rm{Cl}}\)N\({}_{2}\)O\({}_{2}\) (367.62) calculated: C: 49.01%, H: 3.29%, N: 7.62%; found: C: 49.20%, H: 3.30%, N: 7.70%. IR (cm\({}^{-1}\)): 3182 (NH), 3067 (CH, arom. ), 2956 (CH, aliph. ), 1662 (C=O), 1594 (C=N); \({}^{1}\)H NMR (600 MHz, DMSO-\(d_{6}\)): 3.62 (s, 2H, CH\({}_{2}\)), 7.24-7.28 (m, 2H, ArH), 7.31-7.36 (m, 3H, ArH), 7.68-7.70 (m, 1H, ArH), 7.71-7.73 (m, 1H, ArH), 8.33 (s, 1H, =CH), 12.26 (s, 1H, OH), 12.48 (s, 1H, NH); \({}^{13}\)C NMR (150 MHz, DMSO-\(d_{6}\)): 41.19 (CH\({}_{2}\)), 111.22, 120.78, 123.70, 127.24, 128.88, 129.62, 133.40, 135.54, 141.20 (11C\({}_{\rm{ar}}\)), 146.61 (=CH), 153.60 (C\({}_{\rm{ar}}\)), 167. \(N^{\prime}\)-[(\(E\))-(2-hydroxy-3,5-diiodophenyl)methylidene]-2-phenylacetohydrazide (**8**)  
Color: light yellow; M.p. : 240-242 \({}^{\circ}\)C; yield: 82%; for C\({}_{15}\)H\({}_{12}\)I\({}_{2}\)N\({}_{2}\)O\({}_{2}\) (506.08) calculated: C: 35.60%, H: 2.39%, N: 5.54%; found: C: 35.53%, H: 2.38%, N: 5.52%. IR (cm\({}^{-1}\)): 3299 (OH), 3052 (CH, arom. ), 2930 (CH, aliph. ), 1662 (C=O), 1612 (C=N); \({}^{1}\)H NMR (600 MHz, DMSO-\(d_{6}\)): 3.61 (s, 2H, CH\({}_{2}\)), 7.27-7.28 (m, 1H, ArH), 7.32-7.34 (m, 4H, ArH), 7.88 (d, 1H, ArH, \(J\) = 6 Hz), 8.03 (d, 1H, ArH, \(J\) = 6 Hz), 8.23 (s, 1H, =CH), 12.25 (s, 1H, OH), 12.71 (s, 1H, NH); \({}^{13}\)C NMR (150 MHz, DMSO-\(d_{6}\)): 41.15 (CH\({}_{2}\)), 8.52, 88.11, 120.75, 127.23, 128.87, 129.61, 135.57, 139.23, 146.58 (11C\({}_{\rm ar}\)), 146.87 (=CH), 156.95 (C\({}_{\rm ar}\)), 167.23 (C=O).