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Hydroxyl benzoic anhydride dimer compound, preparation method and uses thereof

A technology of hydroxybenzoic anhydride dimer and tetrahydroxydibenzoic anhydride is applied in the fields of hydroxybenzoic anhydride dimer compound, preparation and use, and can solve problems such as low activity and instability

Active Publication Date: 2008-06-18
SHENGHUA GUANGZHOU PHARMA SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] 3,4,5-trihydroxybenzoic acid and its glucose-derived derivatives have the effect of inhibiting HIV-1 integrase (Kane CJ et al. Planta Med 2002May; 68(5):457-9), but the activity is not high
However, it is known that 3,4,5-trihydroxybenzoic acid is unstable under human environmental conditions

Method used

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  • Hydroxyl benzoic anhydride dimer compound, preparation method and uses thereof
  • Hydroxyl benzoic anhydride dimer compound, preparation method and uses thereof
  • Hydroxyl benzoic anhydride dimer compound, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 3,3',4,4',5,5'-hexahydroxydibenzoic anhydride

[0045] Get a 200 milliliter beaker, dissolve 20 grams of 3,4,5-trihydroxybenzoic acid in 100 grams of 1,4-dioxane, add 1 gram of concentrated sulfuric acid (5%) in the solution, and heat it in a Sanyo microwave oven 2450 ( MHz) to dissolve completely, then heated for 3 minutes (200°C), then evaporated 1,4-dioxane to dryness, recrystallized with acetone, then filtered, and dried at 70°C to obtain a reddish-orange substance , yield 96%.

[0046] 1 HNMR (400MHz, DMSO): δ6.901(6H), δ2.486-2.494(4H).IR(KBr, CM -1 ): 3463.6, 3059.2, 2667.5, 1917.4, 1867.5, 1828.9, 1794.6, 1657.6, 1614.7, 1542.6, 1454.5, 1434.8, 1318.0, 1265.5, 1227.4, 1170.1-471.2.

Embodiment 2

[0048] 3,3',4,4'-tetrahydroxydibenzoic anhydride

[0049] Get a 200 ml beaker, dissolve 20 grams of 3,4-dihydroxybenzoic acid in 100 grams of toluene, add 0.5 grams of p-toluenesulfonic acid in the solution, and heat it in a Sanyo microwave oven at 2450 (MHz) until it is completely dissolved, and then heat for 5 Minutes (150°C), then, evaporate toluene to dryness, recrystallize with acetone, filter, and dry at 70°C to obtain an orange substance, 3,3',4,4'-tetrahydroxydibenzoic anhydride, Yield 86%.

[0050] 1 HNMR (400MHz, DMSO): δ6.756-7.321 (4H), δ2.485-2.494 (2H).IR (KBr, CM -1 ): 3546.2, 3205.5, 2652.6, 1871.2, 1845.1, 1676.3, 1600.8, 1526.6, 1466.8, 1419.6, 1380.0, 1346.1, 1298.24, 1190.6, 1126.9-450.9.

Embodiment 3

[0052] 2,2',3,3'-tetrahydroxydibenzoic anhydride

[0053] Take a 200 ml beaker, dissolve 20 grams of 2,3-dihydroxybenzoic acid in 100 grams of benzene, add 2 grams of phosphoric acid and 2 grams of acetic anhydride in the solution, heat it in a Sanyo microwave oven at 2450 (MHz) until completely dissolved, and then Heated for 6 minutes (100°C), then evaporated benzene to dryness, recrystallized with acetone, filtered, and dried at 70°C to obtain an orange substance, 2,2',3,3'-tetrahydroxybenzidine Anhydride, yield 82%.

[0054] 1 HNMR (400MHz, DMSO): δ6.99-7.24(4H), δ2.49(2H).IR(KBr, CM -1 ): IR (KBr, CM -1 ):3377.2,3243.0,3096.5,2578.6,1916.3,1847.1,1794.7,1678.8,1656.6,1598.9,1559.8,1540.9,1474.7,1433.7,1382.37,1354.0,1301.7,1258.0,1233.46,1158.65,1070.3-419.3

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Abstract

The present invention discloses symmetric and asymmetric m-hydroxybenzoic acid dimer compounds with constitutional formula (I), and as well as a method of the preparation of and the function of such products. Basic framework m-hydroxybenzoic acid and as well as hydroxybenzoic acid replaced by the same or different hydroxyl groups are condensed into m-hydroxybenzoic acid dimer compound with a parent nucleus symmetric structure and with the replacement of the same or different number of hydroxyl groups, the pharmacological test proves that the product has the activities of anti-human papillomavirus, herpes virus and resist HIV-1 integrase inhibitors; the product is capable to resist the virus that can integrally enter the chromosome of human cell, inhibit the breeding of the virus that integrally enter into the chromosome, prevent the relapse of virus infection; in addition, the product has antitumor activity.

Description

technical field [0001] The present invention relates to a hydroxybenzoic anhydride compound with a symmetrical or asymmetrical structure, more specifically, to an acid anhydride dimer compound formed by condensation of benzoic acid substituted with two or more hydroxyl groups or the like The compound, its preparation method, and its use as a high-efficiency HIV-1 integrase inhibitor for the preparation of anti-human papillomavirus, herpes virus, HIV and anti-tumor drugs. Background technique [0002] HIV (HIV), herpes virus (HSV), and human papillomavirus (HPV) all have the characteristics of integrating into the chromosomes of human cells, but each has different genetic and metabolic characteristics. [0003] HIV-1 is the virus that causes AIDS, which encodes three enzymes: reverse transcriptase (reverse transcriptase, RT,), protease (Protease, PR) and integrase (Integrase, IN). These three enzymes are essential enzymes necessary for HIV replication and infection. At pres...

Claims

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Application Information

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IPC IPC(8): C07C65/105C07C51/56A61K31/192A61P31/12A61P35/00
Inventor 李健诚秦卫华黄海莲
Owner SHENGHUA GUANGZHOU PHARMA SCI & TECH
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