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Cholesterin derivative containing azobenzol group and its synthesis and use

A technology of cholesterol derivatives and azobenzene groups, applied in the field of cholesterol derivatives, can solve problems such as poor stability, and achieve the effects of easy operation and less harsh reaction conditions

Inactive Publication Date: 2004-09-08
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In addition, the stability of liposomes prepared solely with phospholipids is poor, and a certain amount of cholesterol is often added to increase their stability.

Method used

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  • Cholesterin derivative containing azobenzol group and its synthesis and use
  • Cholesterin derivative containing azobenzol group and its synthesis and use
  • Cholesterin derivative containing azobenzol group and its synthesis and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Dissolve 8mmol of compound 1 in 200ml of anhydrous acetone, add 18mmol of anhydrous K 2 CO 3 , 2 mmol KI or 18-crown-6, and 32 mmol of compound 2, refluxed for 36 h and filtered, the filtrate was spin-dried, and separated by flash column chromatography to obtain compound 3 (90%).

[0025] C 17 H 17 N 2 O 3 Br

[0026] 1 H NMR (300MHz, DMSO, ppm): 8.14-8.11 (2H, d, J=9Hz), 7.94-7.90 (4H, dd, J=6Hz), 7.17-7.14 (2H, d, J=9Hz), 4.16 -4.12 (2H, t, 6Hz), 3.65-3.61 (2H, t, 6Hz), 2.02-1.86 (4H, m).

[0027] MS(EI): 424(M + +47, 100%), 378 (M + +1, 49.16%), 376 (M + -1, 49.71%), 183 (M + -194, 56.65%), 133 (M + -244, 28.83%), 121 (M + -244, 25.66).

[0028] IR: 1681, 1602, 1581, 1501, 1501, 1427, 1277, 1248, 1142.

Embodiment 2

[0030] Add 6 mmol of compound 3 to 100 ml of dichloromethane, and then dropwise add 50 ml of a dichloromethane solution containing 7 mmol of dicyclohexylcarbodiimide. After the solution is clarified, add dropwise 50 ml of a dichloromethane solution containing 7 mmol of compound 4, and react at room temperature for 12 h. Filter, extract with 0.1N hydrochloric acid, then with saturated NaHCO 3 Extraction with aqueous solution, and finally extraction with bromine water, the organic phase was spin-dried, and separated by flash column chromatography to obtain compound 5 (55%).

[0031] C 44 H 61 N 2 O 3 Br

[0032] 1 H NMR (300MHz, CDCl 3, ppm): 8.18-8.15 (2H, d, J=9Hz), 7.96-7.88 (4H, dd, J=9Hz), 7.02-6.99 (2H, d, J=9Hz), 5.44-5.42 (1H, m ), 4.94-4.83 (1H, m), 4.11-4.07 (2H, t, J=6Hz), 3.53-3.49 (2H, t, J=6Hz), 2.50-0.69 (47H, m).

[0033] MS (MALDI): 745.4 (M + ), 747.4 (M + +2).

[0034] IR: 2939, 1722, 1708, 1602, 1500, 1468, 1282, 1257, 1143, 1116.

Embodiment 3

[0036] 3 mmol of compound 5a was refluxed in triethylamine solution for 3 days, filtered while hot, washed with ether, and separated by flash column chromatography to obtain compound 6a (50%). where n=4.

[0037] C 50 H 76 N 3 O 3 Br

[0038] 1 H NMR (300MHz, CDCl 3 , ppm): 8.17-8.14 (2H, d, J=9Hz), 7.95-7.87 (4H, dd, J=9Hz), 7.03-7.00 (2H, d, J=9Hz), 5.44-5.42 (1H, m ), 4.93-4.83 (1H, m), 4.19-4.15 (2H, t, J=6Hz), 3.57-3.47 (8H, m), 2.50-0.69 (56H, m).

[0039] MS (MALDI): 766.6 (M + -80), 768.6 (M + -78).

[0040] IR: 2949, 1715, 1598, 1580, 1499, 1274, 1253, 1139, 1114.

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PUM

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Abstract

The present invention relates to one kind of cholesterin derivative containing aobenzol group and with novel structure, the synthesis of this kind of compounds and their use as light controlled release material in controlling the release of liposome coated medicine. The synthesis process is simple and suitable for industrial production.

Description

technical field [0001] The present invention relates to a class of cholesterol derivatives containing an azophenyl group with novel structures, a method for synthesizing such compounds, and their use in controlling the release of drugs contained in liposomes as light-controlled release materials. technical background [0002] Liposomes are widely known as biofilm models, and liposomes have been used as carriers for many drugs due to their good biocompatibility to reduce drug toxicity and deliver drugs to target sites (T.Boulikas.PCT). Int.Appl.WO 2001093836 A2 13 Dec 2001; T.Ito, T.Yasukochi, K.Mitsuchika and K.Kubo.Jpn.Kokai Tokkyo Koho JP 2002037883 A2 6 Feb2002; L.Harris, G.Batist, R.Belt, D. Rovira, R. Navari, N. Azarnia, L. Welles and E. Winer. Cancer 94(1), 25-36, 2002). The development trend in recent years is to develop intelligent drug release systems, such as pH-sensitive liposomes, temperature-sensitive liposomes, light-sensitive liposomes, etc., because they can...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/28C07J9/00
Inventor 王瑾晔刘新铭
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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