Nucleoside-phenylpropenone hybrid with antiparasitic activity and its preparation method and application
A phenylpropenone and anti-parasitic technology, which is applied in the field of nucleoside-phenylpropenone hybrid and its preparation, can solve problems such as no reports, and achieves simple preparation process, short synthesis route, and remarkable anti-parasitic resistance. The effect of insect activity
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Embodiment 1
[0023] 5-(( E Synthesis of )-3-(3-chlorophenyl)-3-oxopropen-1-yl)-3'-azido-2', 3'-dideoxyuridine (product a)
[0024] Add 5-formyl-3'-azido-2', 3'-dideoxyuridine (0.281 g, 1 mmol) and m-chloroacetophenone (0.155 g, 1 mmol) to ethanol ( 5 mL), then sodium hydroxide (0.060 g, 1.5 mmol) was added, the reaction was stirred at 0°C, and monitored by TLC until the end of the reaction. After the solvent was removed under reduced pressure, the residue was separated by column chromatography to obtain product a (0.293 g) as a white solid with a yield of 70%.
[0025] The structural formula and structural characterization data of product a are as follows:
[0026]
[0027] mp 150-152ºC; 1 H NMR (DMSO- d 6 , 400 MHz) δ: 2.35-2.41 (m, 1H, CH 2 -1),2.48-2.55 (m, 1H, CH 2 -2), 3.60-3.65 (m, 1H, CH 2 -1), 3.71-3.76 (m, 1H, CH 2 -2),3.85-3.87 (m, 1H, CH), 4.42 (q, J = 6.4 Hz,, 1H, CH), 6.07 (t, J = 5.2 Hz,1H, CH), 7.52 (d, J = 15.2 Hz, 1H, CH), 7.58 (t, J = 8.0 Hz, 1H, ArH),...
Embodiment 2
[0030] 5-(( E Synthesis of )-3-(4-chlorophenyl)-3-oxopropen-1-yl)-3'-azido-2', 3'-dideoxyuridine (product b)
[0031]Add 5-formyl-3'-azido-2', 3'-dideoxyuridine (0.281 g, 1 mmol) and p-chloroacetophenone (0.155 g, 1 mmol) sequentially to volume ratio Add sodium hydroxide (0.060 g, 1.5 mmol) to a 1:1 ethanol / water solution (5 mL), and stir the reaction at room temperature, followed by TLC monitoring until the end of the reaction. After the solvent was removed under reduced pressure, the residue was separated by column chromatography to obtain product b (0.251 g) as a white solid with a yield of 60%.
[0032] The structural formula and structural characterization data of product b are as follows:
[0033]
[0034] mp 198-199ºC; 1 H NMR (DMSO- d 6 , 400 MHz) δ: 2.34-2.41 (m, 1H, CH 2 -1),2.48-2.54 (m, 1H, CH 2 -2), 3.60-3.65 (m, 1H, CH 2 -1), 3.72-3.76 (m, 1H, CH 2 -2),3.85-3.87 (m, 1H, CH), 4.43 (q, J = 6.4Hz, 1H, CH), 5.39 (t, J = 5.2 Hz, 1H,OH), 6.07 (t, J = ...
Embodiment 3
[0037] 5-(( E Synthesis of )-3-(4-methylphenyl)-3-oxopropen-1-yl)-3'-azido-2', 3'-dideoxyuridine (product c)
[0038] Add 5-formyl-3'-azido-2', 3'-dideoxyuridine (0.281 g, 1 mmol) and p-methylacetophenone (0.134 g, 1 mmol) to ethanol in sequence (5 mL), then sodium ethoxide (0.102 g, 1.5 mmol) was added, the reaction was stirred at room temperature, and monitored by TLC until the end of the reaction. After the solvent was removed under reduced pressure, the residue was separated by column chromatography to obtain the product c (0.231 g) as a white solid with a yield of 58%.
[0039] The structural formula and structural characterization data of product c are as follows:
[0040]
[0041] mp 199-201ºC; 1 H NMR (DMSO- d 6 , 400 MHz) δ: 2.34-2.40(m, 4H, CH 3, CH 2 -1), 2.48-2.56 (m, 1H, CH 2 -2), 3.60-3.64 (m, 1H, CH 2 -1), 3.72-3.75 (m, 1H, CH 2 -2), 3.84-3.86 (m, 1H, CH), 4.40-4.46 (m, 1H, CH), 5.42 (t, J = 4.8 Hz, 1H,OH), 6.08(t, J = 5.2 Hz, 1H, CH), 7.35 (d,...
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