Tabella 9. Costanti chimico-fisiche e caratteristiche analitiche e spettroscopiche dei derivati 28-34.
n. Z W J Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 28 H OCH3 H 80 173-175 2.588 (s, 3H, -CH3); 3.934 (s, 3H, -OCH3); 7.345-7.518 (m, 3H, Ar-H); 8.637 (s, 1H, Ar-H). C12H10O4 29 H OH H 63 248-250 2.477 (s, 3H, -COCH3); 7.159-7.203 (m, 2H, Ar-H); 7.301-7.345 (m, 1H, Ar-H); 8.564 (d, 1H, Ar-H, J=4.8 Hz); 10.372 (bs, 1H, -OH). C11H8O4 30 OCH3 H H 96 181-183 2.589 (d, 3H, -CH3); 3.8215 (d, 3H, -OCH3); 7.352-7.539 (m, 3H, Ar-H); 8.613 (d, 1H, Ar-H). C12H10O4 31 Cl H H 69 198-200 2.593 (s, 3H, -CH3); 7.524 (d, 1H, Ar-H, J=8.8 Hz); 7.793 (d, 1H, Ar-H, J=8.6 Hz); 8.103 (s, 1H, Ar-H); 8.623 (s, 1H, Ar-H). C11H7O3ClO O O Z W J
n. Z W J Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 32 Cl OCH3 H 87 189-191 2.584 (s, 3H, -COCH3); 3.962 (s, 3H, -OCH3); 7.459 (s, 1H, Ar-H); 7.631 (s, 1H, Ar-H); 8.590 (s, 1H, Ar-H). C12H9O4Cl 33 CH2=CH-CH2 OCH3 H 81 147-149 2.575 (s, 1H, -COCH3); 3.367-3.457 (m, 2H, CH2=CH-CH2); 5.085-5.177 (m, 2H, CH2=CH-CH2); 5.948-6.023 (m, 1H, CH2=CH-CH2); 7.278-7.289 (m, 2H, Ar-H); 8.579 (s, 1H, Ar-H). C15H14O4 34 H H OCH3 75 150-152 2.756 (s, 3H, -CH3); 3.974 (s, 3H, -OCH3); 6.979-7.045 (m, 2H, Ar-H); 7.711 (t, 1H, Ar-H, J=8.5 Hz); 8.621 (s, 1H, Ar-H). C12H10O4
Tabella 10. Costanti chimico-fisiche e caratteristiche analitiche e spettroscopiche dei derivati 35-42.
n. Z W J Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 35 H H H 79 161-164 4.904 (s, 2H, -CH2Br); 7.423-7.533 (m, 2H, Ar-H); 7.764-7.842 (m, 1H, Ar-H); 8.000 (d, 1H, Ar-H, J=7.8 Hz); 8.849 (s, 1H, Ar-H). C11H7O3Br 36 H OCH3 H 65 199-201 3.948 (s, 3H,-OCH3); 4.910 (s, 2H, -CH2Br); 7.381-7.559 (m, 3H, Ar-H); 8.821 (s, 1H, Ar-H). C12H9O4Br 37 H OH H 50 223-225 4.899 (s, 2H, -CH2Br); 7.229-7.294 (m, 1H, Ar-H); 7.379-7.444 (m, 1H, Ar-H); 8.767 (s, 1H, Ar-H); 10.475 (bs, 1H, -OH). C11H7O4Br 38 OCH3 H H 60 135-137 3.829 (s, 3H, -OCH3); 4.907 (s, 2H, -CH2Br); 7.401-7.577 (m, 3H, Ar-H); 8.788 (s, 1H, Ar-H). C12H9O4Br O O O Br W Z Jn. Z W J Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 39 Cl H H 55 187-189 4.901 (s, 2H, -CH2Br); 7.555 (d, 1H, Ar-H, J=9 Hz); 7.798-7.855 (m, 1H, Ar-H); 8.131 (d, 1H, Ar-H, J=2.4Hz); 8.792 (s, 1H, Ar-H). C11H6O3ClBr 40 Cl OCH3 H 60 218-220 3.969 (s, 3H, -OCH3); 4.897 (s, 2H, -CH2Br); 7.539 (s, 1H, Ar-H); 7.666 (s, 1H, Ar-H); 8.764 (s, 1H, Ar-H). C12H8O4ClBr 41 CH2=CH-CH2 OCH3 H 55 156-158 3.379-3.554 (m, 2H, CH2=CH-CH2); 3.920 (s, 3H, -OCH3); 4.885 (s, 2H, -CH2Br); 5.080-5.172 (m, 2H, CH2=CH-CH2); 5.935-6.019 (m, 1H, CH2=CH-CH2); 7.318-7.386 (m, 2H, Ar-H); 8.745 (s, 1H, Ar-H). C15H13O4Br 42 H H OCH3 50 133-135 3.993 (s, 3H, -OCH3); 4.893 (s, 2H, -CH2Br); 7.016-7.088 (m, 2H, Ar-H); 7.761 (t, 1H, Ar-H, J=8.5 Hz); 8.762 (s, 1H, Ar-H). C12H9O4Br
Tabella 11. Costanti chimico-fisiche e caratteristiche analitiche e spettroscopiche dei derivati 43-53.
n. Z W J Y R Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 43 H H H H H 65 165-167 4.591 (d, 2H, -CH2NH, J=5.8 Hz); 5.935 (t, 1H, -NH, J=5.5 Hz); 6.523-6.626 (m, 3H, Ar-H); 7.076 (t, 2H, Ar-H, J=7.8 Hz); 7.403-7.530 (m, 2H, Ar-H). C17H13NO3 44 H H H H COOH 76 193-195 4.678 (d, 2H, -CH2NH, J=5.6 Hz); 6.285 (t, 1H, -NH, J=5.6 Hz); 6.843-6.888 (m, 1H, Ar-H); 7.159-7.229 (m, 3H, Ar-H); 7.410-7.539 (m, 2H, Ar-H) 7.742-7.827 (m, 1H, Ar-H); 8.003 (d, 1H, Ar-H, J=6.6 Hz); 8.718 (s, 1H, Ar-H); 12.534 (bs, 1H, -COOH). C18H13NO5 O O O H N W Z R Y Jn. Z W J Y R Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 45 H H H H COOCH2CH3 67 175-177 1.292 (t, 3H, -CH2-CH3, J=7Hz); 4.27(q, 2H, -CH2-CH3, J=7.1 Hz); 4.635 (d, 2H, -CH2NH, J=7 Hz); 6.199 (bs, 1H, -NH); 6.867 (d, 1H, Ar-H, J=7.2 Hz); 7.176-7.217 (m, 1H, Ar-H); 7.408-7.537 (m, 1H, Ar-H); 7.745-7.980 (m, 1H, Ar-H, J=7.8 Hz); 8.772 (s, 1H, Ar-H). C20H17NO5
46 H OCH3 H H COOH 62 203-205 3.948 (s, 3H, -OCH3);
4.642 (d, 2H, -CH2NH, J=5.6 Hz); 6.269 (t, 1H, -NH, J=5.6 Hz); 6.871 (t,1H, Ar-H, J=4.4 Hz); 7.157-7.189 (m, 3H, Ar-H); 7.324-7556 (m, 3H, Ar-H); 8.742 (s, 1H, Ar-H); 12.688 (bs, 1H, -COOH). C19H15NO6 47 H OH H H COOH 65 217-219 4.605 (d, 2H, -CH2NH, J=4.6 Hz); 6.224 (t, 1H, -NH); 6.802-6.835 (m, 1H, Ar-H); 7.118-7.207 (m, 5H, Ar-H); 7.341-7.388 (m, 1H, Ar-H); 8.663 (s, 1H, -OH); 12.641 (bs, 1H, -COOH). C18H13NO6
n. Z W J Y R Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula
48 OCH3 H H H COOH 61 205-207 3.829 (s, 3H, -OCH3);
4.649 (d, 2H, -CH2NH, J=5.2 Hz); 6.295 (t,1H, -NH, J=5.4 Hz); 6.848-6.880 (m, 1H, Ar-H); 7.165-7.223 (m, 3H, Ar-H); 7.346-7.585 (m, 3H, Ar-H); 8.727 (s, 1H, Ar-H); 12.730 (bs, 1H, -COOH). C19H15NO6 49 Cl H H H COOH 57 210-212 4.660 (s, 2H, -CH2NH); 6.294 (bs, 1H, -NH); 6.874 (d, 1H, Ar-H, J=3); 7.156-7.190 (m, 3H, Ar-H); 7.538-7.613 (m, 1H, Ar-H); 7.763-7.870 (m, 1H, Ar-H); 8.144 (d, 1H, Ar-H, J=3.8 Hz); 8.731 (d, 1H, Ar-H, J=6 Hz); 12.699 (bs, 1H, -COOH). C17H12NO5Cl 50 Cl H H Br COOH 57 210-212 4.670 (s, 2H, -CH2-NH); 6.617 (bs, 1H, -NH); 7.029 (s, 1H, Ar-H); 7.197 (s, 2H, Ar-H); 7.567 (d, 1H, Ar-H, J=9 Hz); 7.789-7.845 (m, 1H, Ar-H); 8.131 (s, 1H, Ar-H); 8.737 (s, 1H, Ar-H); 13.066 (bs, 1H, COOH). C18H10NO5ClBr
n. Z W J Y R Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula
51 Cl OCH3 H H COOH 55 213-215 3.976 (s, 3H, -OCH3);
4.638 (s, 2H, -CH2-NH); 6.838-6.867 (m, 1H, Ar-H); 7.163-7.180 (m, 3H, Ar-H); 7.513 (s, 1H, Ar-H); 7.656 (s, 1H, Ar-H); 8.684 (s, 1H, Ar-H). C19H14NO6Cl 52 CH2=CH-CH2 OCH3 H H COOH 55 193-195 3.419 (d, 2H, CH2=CH-CH2, J=6.2 Hz); 3.948 (s, 3H, -OCH3); 4,609 (s, 2H, -CH2-NH); 5.102-5.190 (m, 2H, CH=CH2-Ph); 6.006-6.089 (m, 1H, CH2=CH-CH2); 6.824-6.855 (m, 1H, Ar-H); 7.163-7.269 (m, 6H, Ar-H, -NH); 8.626 (s, 1H, Ar-H). C22H19NO6
53 H H OCH3 H COOH 61 193-195 3.981 (s, 3H, -OCH3);
4.630 (s, 2H, -CH2-NH); 6.842-6.872 (m, 1H, Ar-H); 7.001-7.186 (m, 5H, Ar-H); 7.738 (t, 1H, Ar-H, J=8.4 Hz); 8.707 (s, 1H, Ar-H). C19H15NO6
Tabella 12. Costanti chimico-fisiche e caratteristiche analitiche e spettroscopiche dei derivati 54-58 e 61-68.
O O W Z N N S R1 R Y J n. Z W J R1 Y R Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 54 H H H H H H 75 255-257 7.355-7695 (m, 9H, Ar-H); 8.611 (s, 1H, Ar-H); 13.117 (bs, 1H, -NH). C18H12N2O2S 55 H H H CH3 H H 65 218-220 2.665 (s, 3H, N-CH3); 7.395-7.593 (m, 8H, Ar-H); 7.871-7.904 (d, 1H, Ar-H, J=6.6 Hz); 7.987 (s, 1H, Ar-H); 8.601 (s, 1H, Ar-H). C19H14N2O2S 56 H H H CH3 H COOH 62 278-280 2.682 (s, 3H, N-CH3); 4.420 (bs, 1H, -COOH); 7.358-8.084 (m, 9H, Ar-H); 8.634 (s, 1H, Ar-H). C20H14N2O4Sn. Z W J R1 Y R Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 57 H H H H H COOEt 70 260-262 1.344 (t, 3H, -CH2CH3, J=7 Hz); 4.3655 (q, 2H, -CH2CH3, J=7.1 Hz); 7.397-7.507 (m, 2H, Ar-H); 7.627-7.740 (m, 3H, Ar-H); 7.909-8.054 (m, 3H, Ar-H); 8.246 (s, 1H, Ar-H); 8.588 (s, 1H, Ar-H); 13.180 (s, 1H, -NH). C21H16N2O4S 58 H H H CH3 H COOEt 98 149-151 1.345 (t, 3H, -CH2CH3, J=7.1 Hz); 2.676 (s, 3H, N-CH3); 4.367 (q, 2H, -CH2CH3, J=7 Hz); 7.400-7484 (m, 2H, Ar-H); 7.580-7.615 (m, 1H, Ar-H); 7.744-7.914 (m, 3H, Ar-H); 8.033-8.086 (m, 3H, Ar-H); 8.633 (s, 1H, Ar-H). C22H18N2O4S
61 H OCH3 H H H COOH 57 >300 3.943 (s, 3H, -OCH3);
7.193-7.239 (m, 1H, Ar-H); 7.344-7.373 (m, 2H, Ar-H); 7.677 (t, 1H, Ar-H, J=7.8 Hz); 7.908-8.036 (m, 3H, Ar-H); 8.232 (s, 1H, Ar-H); 8.566 (s, 1H, Ar-H); 13.164 (bs, 2H, -COOH, -NH). C20H14N2O5S
n. Z W J R1 Y R Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 62 H OH H H H COOH 56 >300 3.381 (s, 1H, -OH); 7.059-7.261 (m, 3H, Ar-H); 7.676 (t, 1H, Ar-H); 7.892-8.032 (m, 3H, Ar-H); 8.235 (s, 1H, Ar-H); 8.533 (s, 1H, Ar-H); 10.367 (bs, 1H, -COOH); 13.134 (bs, 1H, -NH). C19H12N2O5
63 OCH3 H H H H COOH 84 >300 3.851 (s, 3H, -OCH3);
7.073 (d, 1H, Ar-H, J=2.8 Hz); 7.212-7.270 (m, 1H, Ar-H); 7.4325 (d, 1H, Ar-H, J=9 Hz); 7.617 (t, 1H, Ar-H, J=7.9 Hz); 7.894-8.029 (m, 3H, Ar-H); 8.223 (s,1H, Ar-H); 8.516 (s, 1H, Ar-H); 13.175 (bs, 1H, -COOH); 13.279 (bs, 1H, -NH). C20H14N2O5S 64 Cl H H H H COOH 80 >300 7.500-7.543 (m, 1H, Ar-H); 7.639-7.709 (m, 3H, Ar-H); 7.925-8.038 (m, 3H, Ar-H); 8.225 (s, 1H, Ar-H); 8.478 (s, 1H, Ar-H); 13.227 (bs, 2H, -NH, -COOH). C19H11N2O4SCl
n. Z W J R1 Y R Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula 65 Cl H H H Br COOH 61 >300 7.513 (d, 1H, Ar-H, J=9.4 Hz); 7.660-7.696 (m, 2H, Ar-H); 7.994 (s, 1H, Ar-H); 8.094 (s, 1H, Ar-H); 8.219-8.236 (m, 2H, Ar-H); 8.458 (s, 1H, Ar-H); 13.276 (bs, 2H, -COOH, -NH). C19H10N2SO4ClBr
66 Cl OCH3 H H H COOH 70 >300 3.956 (s, 3H, -OCH3);
7.261 (s, 1H, Ar-H); 7.407 (s, 1H, Ar-H); 7.674 (t, 1H, Ar-H, J=8 Hz); 7.927-8.035 (m, 3H, Ar-H); 8.218 (s, 1H, Ar-H); 8.455 (s, 1H, Ar-H); 13.226 (bs, 2H, -COOH, -NH). C20H13N2O5SCl 67 CH2=CH-CH2 OCH3 H H H COOH 78 >300 3.488 (d, 2H, -CH2=CH-CH2, J=6 Hz); 3.930 (s, 3H, -OCH3); 5.018-5.220 (m, 2H, -CH2=CH-CH2); 5.979-6.103 (m, 1H, -CH2=CH-CH2); 7.007 (s, 1H, Ar-H); 7.189 (s, 1H, Ar-H); 7.645-7.717 (m, 1H, Ar-H); 7.914-8.037 (m, 3H, Ar-H); 8.230 (s, 1H, Ar-H); 8.525 (s, 1H, Ar-H); 13.159 (bs, 2H, -NH, -COOH). C23H18N2O5S
n. Z W J R1 Y R Resa (%) p.f. (°C) 1H-NMR (DMSO-d6, ppm) Formula
68 H H OCH3 H H COOH 71 292-294 3.993 (s, 3H, -OCH3);
6.938-7.053 (m, 2H, Ar-H); 7.548-7.709 (m, 2H, Ar-H); 7.878-8.025 (m, 3H, Ar-H); 8.229 (s, 1H, Ar-H); 8.820 (s, 1H, Ar-H); 13.369 (bs, 2H, -COOH, -NH). C20H14N2O5S
