Substituted pyridino imidazole compound and application thereof in preparation of drugs for treating malignant tumor diseases
A pyridoimidazole, malignant tumor technology, applied in the field of medicine, can solve problems such as low overall survival rate, achieve the effects of inhibiting growth and metastasis, broad application prospects, and important theoretical significance
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Embodiment 1
[0059] Embodiment 1: Preparation of W2014
[0060]
[0061] Weigh compound 1, iron powder (3 equivalents) and ammonium chloride (4 equivalents) and dissolve them in 20ml of ethanol, heat at 80°C, cool to room temperature after the reaction is complete, filter the reaction solution through diatomaceous earth and rinse the silicon with an appropriate amount of ethyl acetate. alginate, the organic phase was dried with anhydrous sodium sulfate, and spin-dried to obtain a purple solid compound 2 with a yield of 78%. 1 H NMR (500MHz, CDCl 3 )δ6.85(d, J=7.8Hz, 1H), 6.60(d, J=7.8Hz, 1H), 4.45(s, 2H), 3.28(s, 2H).ESI-MS: 145.0[M+H ]+;
[0062] Weigh compound 3, p-hydroxybenzaldehyde (1.1 equivalents), and potassium carbonate (2 equivalents) and dissolve them in 40ml of acetonitrile, stir at room temperature overnight for reaction, filter after the reaction is complete, spin the organic phase to dry column chromatography and purify to obtain compound 4, the yield 90%, 1 H NMR (40...
Embodiment 2
[0065] Embodiment 2: Preparation of W2014R
[0066]
[0067] Weighed triphenylphosphine (1.8 equivalents) and dissolved it in 80 ml of tetrahydrofuran, under nitrogen protection, slowly added DIAD (1.8 equivalents) to the reaction under ice bath conditions, and after 20 minutes, kept ice bath conditions, successively added compound 6 (1 equivalent) and p-Hydroxybenzaldehyde (1 equivalent) were dissolved in 20 milliliters of tetrahydrofuran and added to the reaction respectively, stirred at room temperature, and the reaction was complete after 10 hours. The organic phase was spin-dried and concentrated, and the residue was purified by column chromatography to obtain compound 7 , with a yield of 44%, 1 H NMR (400MHz, CDCl 3 )δ9.84(s,1H),7.78–7.74(m,2H),7.39–7.36(m,4H),7.32–7.28(m,1H),6.99(d,J=8.7Hz,2H),5.44 (q, J=6.4Hz, 1H), 1.70 (d, J=6.4Hz, 3H).ESI-MS: 227.2[M+H]+;
[0068] Weigh intermediate compound 2 and compound 7 (1.1 equivalent) and dissolve in 10ml methanol, heat ...
Embodiment 3
[0070] Embodiment 3: Preparation of W2014S
[0071]
[0072] Weighed triphenylphosphine (1.8 equivalents) and dissolved it in 80 ml of tetrahydrofuran, under nitrogen protection, slowly added DIAD (1.8 equivalents) to the reaction under ice bath conditions, and after 20 minutes, maintained ice bath conditions, successively added compound 9 (1 equivalent) and p-Hydroxybenzaldehyde (1 equivalent) were dissolved in 20 milliliters of tetrahydrofuran and added to the reaction respectively, stirred at room temperature, and the reaction was complete after 10 hours. The organic phase was spin-dried and concentrated, and the residue was purified by column chromatography to obtain compound 10 , with a yield of 48%, 1 H NMR (400MHz, CDCl 3 )δ9.84(s,1H),7.79–7.74(m,2H),7.40–7.35(m,4H),7.32–7.28(m,1H),6.99(d,J=8.7Hz,2H),5.44 (q, J=6.4Hz, 1H), 1.70 (d, J=6.4Hz, 3H).ESI-MS: 227.2[M+H]+;
[0073] Weigh intermediate compound 2, compound 10 (1.1 equivalent) and dissolve in 10ml methanol, ...
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