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Synthesis and anticancer activity of conjugated phospholipid compounds

A technology of compounds and conjugates, applied in the field of phospholipid compounds, can solve the problems of toxic and side effects, the effect of limiting the use of chemotherapeutic agents, and the decline of leukocytes

Inactive Publication Date: 2004-01-28
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] 5-Fluorouracil (also known as Tegafur, Tegafur) is an anticancer drug that is currently being used clinically, but due to its toxic and side effects, long-term use of it will cause symptoms such as leukopenia, nausea, and vomiting, which greatly limits its use as a chemotherapeutic agent The effect of using

Method used

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  • Synthesis and anticancer activity of conjugated phospholipid compounds

Examples

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Embodiment 1

[0012] Synthesis of rac-1,3-O,O-benzylidene glycerol (1)

[0013] 1mol glycerin and 1.2mol benzaldehyde were reacted at 140-170°C for 3h, distilled under reduced pressure, collected fractions at 180-182°C / 1.1Pa, diluted to 200-300ml by adding ether, and washed successively with 10% K 2 CO 3 and water, and the organic phase was washed with anhydrous K 2 CO 3 Dry, remove the solvent, dilute the residue with a mixture of petroleum ether and benzene, cool to -20°C, filter the precipitated solid, cool the filtrate to -20°C, combine the solids obtained twice and recrystallize with ether, the yield 74%, m.p.80.0-84.0°C.

[0014] Synthesis of rac-2-O-hexadecyl-1,3-O,O-benzylidene glycerol (2)

[0015] Add 2.1 mmol of sodium hydride (80%) to 20 mmol THF cooled to 0°C, add dropwise a solution of 20 mmol of compound (1) dissolved in 30 mL of THF under cooling in an ice-water bath, react at room temperature for 30 min under stirring, and then add dropwise 21 mmol of Hexadecane bromid...

Embodiment 2

[0022] 2-(2'-Tegafur-N 3 -) Synthesis of ethoxy-2-thio-5-octadecyloxy-1,3,2-dioxaphosphorinane (5b)

[0023] The preparation method is the same as the synthesis of Example 1 (5a), colorless viscous liquid, R f =0.65(G 254 Silica gel plate, the developer is ethyl acetate-petroleum ether v / v=1:1), the yield is 40%. C 31 h 54 FN 2 o 7 Elemental analysis of PS: C, 57.40 (57.41); H, 8.72 (8.36); N, 4.32 (4.32). IR(Film)(cm -1 ): 2908, 1715, 1674, 1464, 1262, 1073, 1022, 839, 767, 716, 638. 1 H NMR: (200Mhz, CDCl 3 , δ, ppm) 0.85 (t, 3H, CH 3 ), 1.22 (sb, 30H, 15CH 2 ), 1.52 (m, 2H, CH 2 -C-O), 1.68-2.46 (m, 4H, 2', 3'-2CH 2 ), 3.52(t, 2H, CH 2 N), 3.55-4.33 (m, 11H, 5CH 2 O, OCH), 5.96(m, 1H, 1'-H), 7.35(d, 1H, 6-H, 2 J F-H = 6.2Hz), 31 P NMR: 63.27 63.2.

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Abstract

The phospholipid compound is synthesized through reaction of P(NEt2)3, N3-(beta-ethoxyl) Tegafur, Rac-2-0-alkyl glycerine and monomer sulfur. It has a mouse LA795 lung adenocarcinoma inhibiting rate of 97.4% and a mouse liver cancer inhibiting rate of 81% in the dosage of 50 mM / Kg, higher than 61.4% and 60.5% separately of Tegafur. The present invention has novel and reasonable synthesizing process and high yield.

Description

technical field [0001] The invention belongs to phospholipid compounds. Background technique [0002] 5-Fluorouracil (also known as Tegafur, Tegafur) is an anti-cancer drug that is currently being used clinically, but due to toxic and side effects, long-term use of it will cause white blood cell drop, nausea, vomiting and other symptoms, which greatly limits its use as a chemotherapeutic agent The effect of using. Contents of the invention [0003] The object of the present invention is to provide a phospholipid conjugate compound, which is a conjugate formed by linking tegafur and cycloglycerol phospholipids, which can reduce toxicity and improve drug efficacy. [0004] The present invention is the following general formula compound: [0005] R=CH 3 (CH 2 ) m, m=12-18 synthetic route: [0006] Tegafur [0007] The present invention uses glycerol as raw material, the molar ratio of glycerin and benzaldehyde is (1:1.2), reacts at 140-170...

Claims

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Application Information

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IPC IPC(8): A61K31/7064A61P35/00C07F9/6571C07H19/06
Inventor 陈茹玉张成祥王士贤
Owner NANKAI UNIV
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