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Cephalin analogue as well as preparation method and application thereof

A technology of cephalin and analogs, applied in the fields of medicinal chemistry and therapeutics, can solve the problems of poor water solubility and strong toxicity of camptothecin

Inactive Publication Date: 2018-11-13
NORTHEAST FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Camptothecin (CPT) is an alkaloid extracted from the unique plant camptothecin in my country. Camptothecin has strong anti-tumor activity and has obvious inhibitory effect on a variety of solid tumors and leukemia. However, camptothecin Poor water solubility and strong toxicity limit its application in tumor therapy

Method used

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  • Cephalin analogue as well as preparation method and application thereof
  • Cephalin analogue as well as preparation method and application thereof
  • Cephalin analogue as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1 prepares camptothecin-20-O-succinyl monoester (intermediate a)

[0062]

[0063] Dissolve 1.0 gram (0.01 mole) of succinic anhydride in 100 milliliters of pyridine, add 3.5 grams (0.01 mole) of camptothecin, reflux for 24 hours, cool to room temperature, pour the reaction solution into 500 milliliters of petroleum ether, filter . Collect the precipitate, and use silica gel column chromatography (dichloromethane:methanol=100:1) to obtain 3.9 g of light yellow camptothecin-20-O-succinyl monoester, with a yield of 87%.

[0064] 1HNMR (300MHz, DMSO-d6, ppm): δ0.90 (3H, t, H-19), 1.96 (2H, m, H-18), 2.52-2.75 (4H, m, -OOCC H 2 C H 2 COO-), 5.20 (2H, s, H-5), 5.50 (2H, s, H-17), 6.89 (1H, d, N-H), 7.14 (H, s, H-14), 7.72 (1H, q, H-10), 7.87 (H, t, H-11), 8.00 (1H, d, H-12), 8.14 (1H, d, H-9), 8.42 (1H, t, N-H), 8.65 (1H, s, H-7).

[0065] ESIMS m / z: 539.3(M-1) -

Embodiment 2

[0066] Example 2 Preparation of 1-O-stearyl-3-O-(camptothecin-20-O-succinyl)glycerol (intermediate b)

[0067]

[0068] Dissolve 4.5 g (0.01 mol) of camptothecin-20-O-succinyl monoester in 500 ml of dichloromethane, cool to 0°C, slowly add 0.74 g (0.01 mol) of glycidol dropwise under stirring, After stirring for 24 hours at ℃, 3.1 grams (0.01 mole) of stearyl chloride and 2.0 grams of sodium carbonate were added successively, warmed up to room temperature, stirred for 24 hours, filtered, and the filtrate was concentrated under reduced pressure, and the concentrated solution was subjected to silica gel column chromatography (two Chloromethane:methanol=25:1), to obtain 1.5 g of yellow 1-O-stearoyl-3-O-(camptothecin-20-O-succinoyl)glycerol with a yield of 18%.

[0069] 1HNMR (300MHz, DMSO-d6, ppm): 1.96 (2H, m, H-18), 2.29 (2H, m, -OOC C H 2 -), 2.52-2.75 (4H, m, -OOCC H 2 C H 2 COO-), 4.19-4.26 (4H, dd, -OC H 2 -CHOH-C H 2 O-), 4.56 (1H, m, -OCH 2 -C H OH-CH 2 O-...

example 3

[0070] Example 3 Preparation of 1-O-stearyl-3-O-(camptothecin-20-O-succinyl)-2-O-glycerol phosphoethanolamine (cephalin analogue)

[0071]

[0072] Dissolve 0.8 g (0.001 mol) of 1-O-stearyl-3-O-(camptothecin-20-O-succinoyl)glycerol in 50 ml of tetrahydrofuran-pyridine mixture with a volume ratio of 4:1 , cooled to 0°C, and added 0.3 g (0.001 mole) of 2-phthalimide ethyl-phosphoryl dichloride under stirring. At 0°C, after stirring for 10 hours, 40 ml were added successively with a volume ratio of 1: 3 tetrahydrofuran-absolute ethanol mixture, 0.2 g of hydrazine hydrate (12 g), heated to 50 ° C, stirred for 2 hours, after the reaction was completed, dropwise added 2N hydrochloric acid to adjust the pH value to 5, cooled to room temperature, refrigerated and centrifuged, discarded In the supernatant, the centrifuged residue was washed 3 times with water, and then freeze-dried to obtain 1.1 g of an orange-yellow solid, which was subjected to silica gel column chromatography (di...

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Abstract

The invention provides a cephalin analogue shown as a formula (I). The invention further provides a preparation method of the cephalin analogue and the application in preparation of antitumor drugs.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and therapeutics, in particular to a cephalin analogue, a preparation method and its use as an antitumor drug. Background technique [0002] Cephalin (ie phosphatidylethanolamine) is a phospholipid formed by condensation of diglyceride, phosphoric acid and ethanolamine. Cephalin is widely distributed in animals, especially enriched in the brain and spinal cord. Cephalin is an important part of nerve cell membrane, participates in regulating the metabolic activities of nerve cells, and affects a series of important functions of nerve tissue, such as cell permeability, myelin sheath formation, mitochondrial transfer, oxidation and phosphorus oxygenation, etc. Oral cephalin can be directly used by the human brain to repair nerve cell membranes and restore the normal metabolism of neurons. Cephalin is related to blood coagulation, and thromboplastin is composed of cephalin and protein, exists in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561A61K31/675A61P35/00
CPCA61P35/00C07F9/6561
Inventor 井立佳郑健丁为民王洋阎秀峰于涛
Owner NORTHEAST FORESTRY UNIVERSITY
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