Hydrophilic pyridine compound, intermediate and preparation method and application thereof
A compound and hydrophilic technology, applied in the field of hydrophilic pyridine compounds, can solve the problems of low dynamic range, target specificity to be improved, weak imaging signal of prostate cancer cells, etc.
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Embodiment 1
[0158] The preparation of embodiment 1 compound V---VIII
[0159]
[0160] General synthetic procedure: 1.0 mmol of substrates 1-4, 5.0 mmol of oxidizing agent H under general laboratory conditions 5 IO 6 , 0.2 mmol RuCl 3 Catalyst, add 100mL CCl 4 with 250mL of water. After stirring for 24 hours, the aqueous layer was collected and acidified to pH=1 with 3N HCl. The aqueous layer was then extracted with ethyl acetate and washed with Na 2 SO 4 Drying and evaporation of volatiles gave the product 0.40-0.60 mmol as a yellow grease (40-60% yield). 1 H NMR and MS data are consistent with literature reports. Add 5mL of thionyl chloride and reflux for 1-2 hours, drain the solvent, dissolve it with chloroform and filter, drain the solution quantitatively, and continue to use it.
Embodiment 2
[0161] The preparation of embodiment 2 compound IX-XVIII series
[0162]
[0163]
[0164] Compound IX-XVIII synthesis steps: 1.0mmol substrate, 1.0mmol piperidine, 5.0mL CH 3 CN, the reaction mixture was reacted at 80°C for 10-20 hours, and stirred until the reaction was completed. The reaction mixture was partitioned between ethyl acetate and saturated brine. The organic solvent phase was dried in magnesium sulfate, and the solvent was drained, and the crude product was separated on a silica gel column, using ethyl acetate and methanol (90-95:10-5, v / v) as the mobile phase. Among them, the raw substrates 5-10 are derived from the esterification of their respective diacids, and are not purified and separated.
Embodiment 3
[0165] The preparation of embodiment 3 compound I1_3AAA-I1_3DDD and II3_3AAA-II3_3DDD
[0166]
[0167] General synthetic procedure: 1.0 mmol substrate IV, 1.2 eq V, 3.0 eq pyridine, 5.0 mL CH 2 Cl 2 , and the reaction mixture was stirred at room temperature until the reaction was complete. The solvent was drained, and the crude product was separated with a silica gel column, using ethyl acetate and methanol (90-95:10-5, v / v) as the mobile phase.
[0168]
[0169] 1.0mmol substrate I1_3BBB or II3_3BBB, 5eq Me 3 N, 1.1 eq Me 3 SiOTf, 5.0 mL CH 2 Cl 2 , and the reaction mixture was stirred at room temperature until the reaction was complete. The solvent was drained, and the crude product was separated with a silica gel column, using ethyl acetate and methanol (90-95:10-5, v / v) as the mobile phase.
[0170] Compound I1_3AAA, yield 78%, purity >95%, 1 H NMR (400MHz; DMSO-d 6 ),δ12.2(brs,1H,CO 2 H),9.01(d, 3 J HH =8.9Hz,1H,Ar-H),8.01(d, 3 J HH =8.9Hz,1H,Ar-H),8....
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