Novel heterocyclic aromatic hydrazone derivative, pharmaceutically acceptable salt, preparation method and application thereof
A technology of heterocyclic aromatic hydrazones and derivatives, which is applied in the field of medicine, can solve the problems of drugs with low toxic and side effects, and achieve the effects of low toxic and side effects, simple synthesis, and novel preparation methods
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Embodiment 1
[0049] Example 1: 5-(4-Chlorophenyl)-2-(2-(bis(pyridin-2-yl)methylene)hydrazino)thiazole
[0050]
[0051] Preparation method: In a fume hood, under dry conditions, in a 25mL single-necked round bottom flask, add 10mmol of dipyridone and 10.25mmol of thiosemicarbazide to 10ml of absolute ethanol, and then add two drops of ice Acetic acid catalyst, stirred and reacted at 80°C for about 4 hours, TLC followed the reaction, after the reaction was completed, let it stand for cooling, the precipitated solid was filtered and dried, then dissolved and recrystallized with absolute ethanol, and the recrystallized white crystal was obtained as intermediate.
[0052] Take 0.25mmol of the above-mentioned intermediate and place it in a 25mL single-necked round bottom flask, add 5ml of ethanol to dissolve, then add α-bromo-4-chloroacetophenone, add a magnet, stir the reaction at room temperature, and follow the reaction by TLC. After about 4h Finish the reaction, filter and wash with eth...
Embodiment 3
[0057] Example 3: 4-(2-Chlorophenyl)-2-(2-(bis(pyridin-2-yl)methylene)hydrazino)thiazole
[0058]
[0059] The preparation method is the same as in Example 1, except that α-bromo-2-chloroacetophenone is used instead of α-bromo-4-chloroacetophenone in Example 1 to obtain the yellow powdery target compound. The combined yield of the two steps is 82%. Confirmation data for the target compound: 1 H NMR (600MHz, DMSO-d 6 )δ14.14(s,1H),8.90(d,J=5.1Hz,1H), 8.60(d,J=4.8Hz,1H),7.99(q,J=6.9,6.4Hz,2H),7.96– 7.89(m,2H),7.86(d,J=7.8Hz,1H),7.65(s,1H),7.62(d,J=8.0Hz,1H),7.58(dd,J=7.6,5.0Hz,1H ), 7.50–7.43(m,2H),7.38(dd,J=8.0,2.1Hz,1H).
Embodiment 4
[0060] Example 4: 2-(2-(bis(pyridin-2-yl)methylhydrazino)-4-(4-fluorophenyl)thiazole
[0061]
[0062] The preparation method is the same as in Example 1, except that α-bromo-4-fluoroacetophenone is used instead of α-bromo-4-chloroacetophenone in Example 1 to obtain the yellow powdery target compound. The combined yield of the two steps is 80%. The confirmation data for the target compound is: 1 H NMR (600MHz, DMSO-d6) δ8.96(d, J=5.1Hz, 1H), 8.60(d, J=5.0Hz, 1H), 8.19(t, J=7.2Hz, 1H), 8.07(t ,J=7.8Hz,1H),8.01(d,J=8.0Hz,1H),7.94–7.87(m,2H),7.79(d,J=8.1Hz,1H),7.73(t,J=6.5Hz ,1H),7.54(dd, J=7.5,5.0Hz,1H),7.47(s,1H),7.26(t,J=8.9Hz,2H).
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