Cholesterol derivative containing azobenzene group, and its synthesizing method 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: 2006-10-25
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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  • Cholesterol derivative containing azobenzene group, and its synthesizing method and use
  • Cholesterol derivative containing azobenzene group, and its synthesizing method and use
  • Cholesterol derivative containing azobenzene group, and its synthesizing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Dissolve 8mmol of compound 1 in 200ml of anhydrous acetone, add 18mmol of anhydrous K 2 CO 3 , 2mmol KI or 18-crown-6, and 32mmol compound 2 were refluxed for 36h and filtered, the filtrate was spin-dried and separated by flash column chromatography to obtain compound 3 (90%).

[0026] C 17 h 17 N 2 o 3 Br

[0027] 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).

[0028] 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).

[0029] IR: 1681, 1602, 1581, 1501, 1501, 1427, 1277, 1248, 1142.

Embodiment 2

[0031] Add 6mmol of compound 3 to 100ml of dichloromethane, and then dropwise add 50ml of a dichloromethane solution containing 7mmol of dicyclohexylcarbodiimide. After the solution is clarified, add dropwise 50ml of a dichloromethane solution containing 7mmol of compound 4, and react at room temperature for 12h. Filter, extract with 0.1N hydrochloric acid, then wash 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%).

[0032] C 44 h 61 N 2 o 3 Br

[0033] 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).

[0034] MS (MALDI): 745.4 (M + ), 747.4 (M + +2).

[0035] IR: 2939, 1722, 1708, 1602, 1500, 1468, 1282, 1257, 1143, 1116.

Embodiment 3

[0037] 3 mmol of compound 5a and 5 ml of diethylamine were refluxed in chloroform for 3 days, filtered after cooling, washed with chloroform, and separated by flash column chromatography to obtain compound 6a (50%). where n=4.

[0038] C 48 h 71 N 3 o 3

[0039] 1 HNMR (300MHz, CDCl 3 , ppm): 8.19-8.16 (2H, d, J = 9Hz), 7.97-7.89 (4H, dd, J = 9Hz), 7.02-6.99 (2H, d, J = 9Hz), 5.44 (1H, m), 4.93-4.83(1H, m), 4.11-4.07(2H, t, J=6Hz), 3.23-3.16(6H, m), 2.51-0.69(53H, m)

[0040] MS (MALDI): 737 (M + ), 738 (M + +1), 739(M + +2)

[0041] IR: 2926, 2854, 1713, 1601, 1583, 1502cm -1 .

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PUM

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Abstract

The invention relates to a cholesterol ramification containing azobenzene group and the compounding method, and the application as light controlling releasing material. It has simple method, and is suitable for industrializing manufacturing.

Description

technical field [0001] The invention relates to a class of cholesterol derivatives containing azophenyl group with novel structure, a synthesis method of this compound, and its use as a light-controlled release material in controlling the release of liposome-encapsulated drugs. technical background [0002] Liposome (liposomes) is widely known as a biomembrane model, and liposome has been used as a carrier of many drugs to reduce the toxicity of the drug and deliver the drug to the target site (T.Boulikas.PCT) because of its good biocompatibility. 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 liposomes sensitive to pH, liposomes sensitive to temperature, liposomes sensitive to light, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00A61K47/28
Inventor 王瑾晔王玉炉陈永魁
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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