Anti-tumour uracil compound and lipid composition thereof
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A lipid composition and compound technology, applied in the field of medicinal chemistry, can solve problems such as poor patient compliance, high incidence of adverse reactions, and short plasma half-life
Pending Publication Date: 2021-04-09
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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In addition, the plasma half-life of this product is short (t1 / 2: 5-20min), requiring continuous intravenous administration (oral absorption is incomplete and difficult to predict), so the patient's compliance is poor (Shimma N, et al. Bioorganic & Medicinal Chemistry 8 (2000) 1697 -1706)
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Embodiment 1
[0086] Example 1 , (5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl n-hexyloxyformate
[0087]
[0088] Commercially available 5-fluorouracil (compound of formula II, 1.3 g, 0.01 mol) was dissolved in 15 mL of 37% formaldehyde solution, stirred at 50° C. for 3 hours, and the reaction was detected by TLC. The reaction solution was concentrated to dryness under reduced pressure to obtain compound III, which was used in the next reaction.
[0089] Dissolve 0.01 mol of compound III obtained above in 20 mL of dichloromethane, add triethylamine (2.02 g, 0.02 mol), then add hexyloxychloroformate (III', 1.97 g, 0.012 mol) in batches, and stir at room temperature for 2 hours , TLC monitored the end of the reaction. The reaction solution was washed successively with saturated brine and saturated sodiumbicarbonate solution, the organic phase was concentrated, and the residue was subjected to silica gelcolumn chromatography (eluent V 石油醚 :V 乙酸乙酯 =5: 1) Separation and puri...
[0093] Referring to the method of Example 1, compound III was reacted with n-decyloxyformyl chloride to obtain the title compound as a white solid, which can be referred to as compound 2 in the present invention.
[0094] 1 H NMR (500MHz, CDCl 3 )δ8.59(s,1H),7.65(d,J=5.36Hz,1H),5.67(s,2H),4.20(t,J=6.88Hz,2H),1.33-1.25(m,16H), 0.87(t,J=6.89Hz,3H).
[0097] Referring to the method of Example 1, compound III was reacted with n-tetradecyloxycarbonyl chloride to obtain the title compound as a white solid, which may be referred to as compound 3 in the present invention.
[0098] 1 H NMR (500MHz, CDCl 3 )δ8.63(s,1H),7.62(d,J=5.36Hz,1H),5.66(s,2H),4.19(t,J=6.86Hz,2H),1.34-1.25(m,24H), 0.87(t,J=6.99Hz,3H).
[0099] MS-ESI(m / z):401(M+H) + .
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technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a method for improving the antitumor activity of 5-fluorouracil, in particular to a group of 5-fluorouracil prodrugs with antitumor activity, a preparation method thereof, and an antitumor application. In addition, the present invention also provides the lipid composition of the above-mentioned 5-fluorouracilprodrug and the preparation method of the lipid composition. The lipid composition of the present invention exhibits excellent technical effects. Background technique [0002] Fluorouracil, Fluorouracil, also known as 5-fluorouracil, chemical name is 5-fluoro-2,4(1H,3H)-pyrimidinedione, CAS number 51-21-8, molecular formula C4H3FN2O2, molecular weight 130.08, its chemical structure is as follows As shown in (II): [0003] [0004] 5-Fluorouracil is the first pyrimidine anti-metabolite synthesized according to a certain idea, which is converted into 5-fluorodeoxyuridine ...
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