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Nitrogen-containing polyhydroxy fragrant compounds, preparation and uses thereof

A compound and polyhydroxyl technology, which is applied in the field of nitrogen-containing polyhydroxyaromatic compounds and their preparation, can solve the problems of incomplete eradication of viruses in the body, high price, and limited efficacy, and achieve the effect of improving integrase inhibitory activity and selectivity

Inactive Publication Date: 2009-05-13
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The efficacy of these drugs is limited by the rapid emergence of resistance due to the high susceptibility of reverse transcriptases and proteases to mutations
Antiviral combination therapy (combination therapy) (see De clercq E. Biochim Biophys Acta, 2002, 1587 (2-3): 258-275), that is, combined use of reverse transcriptase inhibitors and protease inhibitors for treatment, can be used in In the short term, the virus in the patient's blood is rapidly reduced to an undetectable level, but the side effects of the drug itself and the interaction between the drugs make it difficult for the patient to tolerate for a long time, which limits the application of these drugs
Fusion inhibitors are recently listed anti-HIV drugs, which block HIV1 from entering host cells by inhibiting virus and cell fusion (seeing Fung HB, Guo Y. Clin Ther, 2004, 26 (3): 352-378.), but its It is expensive and cannot completely eradicate the virus in the body, so it is necessary to find drugs that act on new targets of the virus

Method used

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  • Nitrogen-containing polyhydroxy fragrant compounds, preparation and uses thereof
  • Nitrogen-containing polyhydroxy fragrant compounds, preparation and uses thereof
  • Nitrogen-containing polyhydroxy fragrant compounds, preparation and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1. Preparation of 4-(N-substituted phenyl or benzyl-amino)-sulfa-1-aniline 4

[0036]Add 120.0mmol of substituted aniline or benzylamine and dry pyridine (10mL, 123.9mmol) into a 100mL three-necked flask equipped with a drying tube, add 216.0mmol of p-acetamidobenzenesulfonyl chloride in batches under ice bath conditions, and stir after addition. React for 10min, remove the ice bath, stir at room temperature for 4h, add distilled water (100mL), stir for 20min, precipitate a solid, filter, wash the filter cake three times, dissolve the solid with 10% sodium hydroxide solution, filter, and use 18% hydrochloric acid solution for the filtrate Adjust pH 3~4, precipitate solid, filter, wash filter cake three times, and dry to obtain compound 3. Add compound 3 into a 50mL round bottom flask, add sodium hydroxide solution (20mL) and methanol (12mL) at a concentration of 5mol / L , The reaction was stirred at 70°C for 3 hours, the pH was adjusted to 6 with a hydrochloric acid ...

Embodiment 23

[0040] Example 2.3 Preparation of 4,5-Triacetylgalloyl Chloride 5

[0041] Add gallic acid 6 and ethyl acetic anhydride with a molar ratio of 1:3 to 10 and 5.0 mL of pyridine into a 50 mL round bottom flask. Stir and react for 20 hours at 25°C. Add 200 mL of ether or water to the reaction solution and let it stand. The white precipitate is separated out, filtered, recrystallized with acetone / cyclohexane, filtered and dried to obtain the intermediate; add the intermediate and thionyl chloride with a molar ratio of 1:2~10 to 50mL equipped with a drying tube and a condenser tube In a round bottom flask, heated in an oil bath, stirred at 70-85°C for 3-10 hours, and evaporated under reduced pressure at 40°C to remove the solvent to obtain compound 5, which was diluted by adding 10 mL of acetone for later use.

Embodiment 33

[0042] Example 3.3 Preparation of 4,5-triacetoxy-N-(4-(N-substituted aniline or benzylaminosulfonyl)phenyl)benzamide 7

[0043] Add 4-(N-substituted aryl-amino)-sulfa-1-aniline 4, 10 mL of dry acetone and pyridine to a 100 mL three-necked flask equipped with a drying tube and a constant pressure dropping funnel, and slowly under ice Add acid chloride 5 prepared in Example 2 above, the molar ratio of acid chloride 5 to compound 4 is 1:1 to 2; the molar ratio of acid chloride 5 to pyridine is 1:1 to 2 in acetone, and the reaction is completed in about 1 hour. 10min, remove the ice bath, stir at room temperature for 15-30h, filter, evaporate the solvent under reduced pressure to obtain an oily substance, add 80mL of distilled water and stir to precipitate a solid, filter and dry; the crude product is purified by silica gel column chromatography, petroleum ether / ethyl acetate gradient For elution, collect the combined product eluent, evaporate the solvent under reduced pressure, add a...

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Abstract

The invention relates to a nitrogen-containing polyhydroxy arometic compound having a structure as shown in a general formula 1, wherein R1 is hydrogen, methyl or fluorine; R2 is hydrogen, methyl, acetyl, fluorine, chlorine or bromine; R3 is hydrogen, methyl, butyl, methoxyl, ethoxyl, fluorine, chlorine, bromine or nitro; R4 is hydrogen, methyl, acetyl, fluorine, chlorine or bromine; and n is 0 or 1. The invention also relates to a method for preparing the nitrogen-containing polyhydroxy arometic compound in the general formula 1. The compound has obvious inhibitory activity to HIV integrase, and is used for preparing anti-AIDS medicine. The n is equal to 0 or 1.

Description

Technical field [0001] The invention relates to the field of organic compound synthesis and medical applications, in particular to nitrogen-containing polyhydroxy aromatic compounds and their preparation methods and pharmaceutical applications. Background technique [0002] Human immunodeficiency virus (HIV) is the pathogen of AIDS (acquired immune deficiency syndrome, AIDS), divided into HIV1 and HIV-2 types. HIV-1 is prevalent all over the world, and HIV-2 is mainly confined to western Africa. HIV-1 replication requires three key enzymes: reverse transcriptase, protease and integrase. The current drugs for the treatment of AIDS mainly target reverse transcriptase and protease to prevent reverse transcription of single-stranded RNA viruses or inhibit viral protein cleavage and mature virus release. Since reverse transcriptase and protease are highly susceptible to mutations, the effectiveness of these drugs is limited by the rapid emergence of drug resistance. Antiviral combinat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/38C07C303/36A61K31/63A61P31/18
Inventor 赵桂森刘川王朋谭艳梅钟嫄
Owner SHANDONG UNIV
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