Purple bergenia element pentaacetylate and its uses

A technology of pentaacetylated compound and petogenin, which is applied in the field of medicine, can solve the problems of poor oral absorption, weak antitussive and antiasthmatic effects, etc., to overcome poor oral absorption, weak antitussive and antiasthmatic effects, and obvious drug potentiating effect

Inactive Publication Date: 2006-02-15
王刚 +2
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The use of the petracenin pentaacetylate obtained in the present invention for antitussive and asthma-relieving purposes, compared with the crude drug petracenin, animal experiments have shown that it has obvious drug effect enhancement, and the petracenin p

Method used

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  • Purple bergenia element pentaacetylate and its uses
  • Purple bergenia element pentaacetylate and its uses

Examples

Experimental program
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Effect test

Embodiment 1

[0008] Example 1: Weigh 5g of petracenin and place it in a 250ml reaction bottle, add 18g of sodium acetate and 100ml of acetic anhydride, heat and stir at 60°C, and react for 3 hours, pour the reaction solution into 500ml of distilled water, and place in a refrigerator at 4°C overnight , a white solid precipitated, the precipitate was washed with water until neutral, and recrystallized with chloroform-petroleum ether with a volume ratio of 5:1 to obtain about 5 g of white granular crystals, with a yield of about 80%, mp: 203-205 ° C, This product is easily soluble in chloroform, acetone, and ether, but less soluble in methanol and ethanol.

[0009] EI-MS: 538(5)[M + ], 496(100), 454(10), 412(15), 376(65), 292(90), 274(65).

[0010] 1 H-NMR (CDCl 3 , 400MHz): 7.06(1H, s, H-4), 4.93(1H, d, J=10.4, H-1'), 4.15(1H, m, H-2'), 4.10(1H, m, H -6a'), 3.88 (3H, s, OCH 3 ), 3.85(1H, t, J=9.0, H-3'), 3.75(1H, m, H-6b'), 3.65(1H, m, H-5'), 3.52(1H, t, J= 9.0, H-4'), 2.10-1.95 (15H, ...

Embodiment 2

[0012] Example 2: Weigh 10g of petracenin and place it in a 500ml reaction bottle, add 30g of sodium acetate and 250ml of acetic anhydride, heat and stir at 90°C, and react for 5 hours, pour the reaction solution into 1000ml of distilled water, and place in a refrigerator at 4°C overnight , a white solid was precipitated, the precipitate was washed with water until neutral, and recrystallized with chloroform-petroleum ether with a volume ratio of 5:1 to obtain about 9 g of white granular crystals, with a yield of about 75%.

Embodiment 3

[0013] Example 3: Weigh 1 g of petracenin and place it in a 50 ml reaction bottle, add 3 g of sodium acetate, 50 ml of acetic anhydride, heat and stir at 55°C, and react for 1.5 hours, pour the reaction solution into 100 ml of distilled water, and place in a refrigerator at 4°C overnight , a white solid was precipitated, the precipitate was washed with water until neutral, and recrystallized with chloroform-petroleum ether with a volume ratio of 5:1 to obtain about 0.8 g of white granular crystals, with a yield of about 80%.

[0014] The role of petracenin pentaacetyl in antitussive and antiasthmatic is confirmed by animal experiments.

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Abstract

The invention provides a Bergenini penta-acetyl, whose chemical name is (2R,3R,4R,4aS,10bS)-2-(acetoxymethyl)-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydr o pyrano[3,2-c]isochromene-3,4,8,10-tetrayl tetraacetate, and is prepared from Bergenini as lead compound through butanoylation reaction, the hydroxyl on the precursor is blocked so as to enhance the lipophilicity. The Bergenini penta-acetyl can be used for preparing medicine for relieving cough. The invention further provides a compound preparation containing the Bergenini penta-acetyl.

Description

technical field [0001] The invention relates to the application of petracenin pentaacetyl in the treatment of antitussive, antiasthma, anti-inflammatory and expectorant, and belongs to the field of medicine. Background technique [0002] Bergeninum (Bergeninum) is also known as pyroglycin, phyllophyllin, saxifrage, bergamot and so on. It is widely distributed in many plants of Saxifragaceae and Zijinbudaceae, and its content is relatively high. The 1990 edition of the Pharmacopoeia of the People's Republic of China records that petracenin is an antitussive drug for the treatment of chronic bronchitis. Modern pharmacological studies have proved that petracenin has a significant selective inhibitory effect on the cough center. Animal experiments have found that there is no tolerance to continuous administration for 23 days, and it has no toxic effects on the growth and development of mice and major organs. In recent years, it has been reported that petracenin has anti-inflamm...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/366A61K31/4402A61P11/06A61P11/10A61P11/14C07D311/00
Inventor 王刚刘吉开麻兵继
Owner 王刚
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