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Preparation method of a class of thiol-containing aromatic compounds and its application in anti-HIV virus

A technology of compounds, reactions, applied in the field of biochemistry

Active Publication Date: 2019-05-17
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, there are no drugs and therapies that can effectively treat AIDS in the world, and only drugs can be used to properly control the proliferation of HIV in the human body

Method used

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  • Preparation method of a class of thiol-containing aromatic compounds and its application in anti-HIV virus
  • Preparation method of a class of thiol-containing aromatic compounds and its application in anti-HIV virus
  • Preparation method of a class of thiol-containing aromatic compounds and its application in anti-HIV virus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] 1, prepare compound shown in formula I of the present invention (R 1 for -H,R 2 for -H,R 3 for -CH=CH-CH=C(CH 3 ) 2 , R 4 for -H,R 5 is -H, X is -S-, Y is -SH, n is 1) the name is 2-[4-(4-methyl-1,3-pentadiene)phenylthio]ethanethiol. 10mmol 2-chloroethanol, 10mmol TBDPSCl and 12mmol imidazole were reacted in 20mL DMF at room temperature for 2-5h, then extracted, separated by column chromatography and sent to the next step. Stir 10mmol 4-(4-methyl-1,3-pentadiene)thiophenol and 20mmol sodium bicarbonate in 25mL DMF for half an hour, then slowly add the above-mentioned product dropwise and react 5-10 Hours, after the reaction was completed, extraction and column chromatography gave a pale yellow solid. After dissolving the above solid in DCM, add two equivalents of acetyl chloride and several drops of methanol, react at room temperature for 2-8 hours, and separate the product 2-[4-(4-methyl-1,3-pentadiene) by column chromatography phenylthio]ethanol. Finally, diss...

Embodiment 2

[0081] 1, prepare compound shown in formula I of the present invention (R 1 for -H,R 2 for -H,R 3 for -CH=CH-CH=C(CH 3 ) 2 , R 4 for -H,R 5 is -H, X is -O-, Y is -SH, n is 2) the name is 3-[4-(4-methylpentyl-1,3-diene)phenoxy]propane-1-sulfur alcohol.

[0082] 10mmol of p-Hydroxybenzaldehyde, 11mmol of 1,3-dibromopropane, 12mmol of potassium carbonate and catalytic amount of potassium iodide were refluxed overnight in DMF, separated by column chromatography to obtain 1-(4-formylphenyl)-3-bromo-propanol ; Dissolve 6mmol of sodium hydride and 5mmol of (2-methallyl)triphenylphosphine bromide in THF, cool in an ice bath to 0°C, and add 10mmol of 1-(4-formylbenzene) dropwise to the above solution Base)-3-bromo-propanol THF solution, after the dropwise addition, transfer to room temperature for reaction for 10-15 hours. Then column chromatography separated 1-(3-bromopropoxy)-4-(4-methylpentyl-1,3-dienyl)benzene. Finally, react the product obtained above with two equivalents...

Embodiment 3

[0089] 1, prepare compound shown in formula I of the present invention (R 1 for -H,R 2 for -H,R 3 for -CH 3 , R 4 for -H,R 5 -H, X is -S-, Y is -NH 2 , n is 2) the name is 3-(p-tolylthio)-1-propylamine.

[0090] 10mmol p-cresol, 30mmol 2-(3-bromopropyl)isoindoline-1,3-dione and 11mmol potassium tert-butoxide were reacted at room temperature in 20mL DMF for 8 hours, and separated by column chromatography to obtain 2-[3 -(p-tolylthio)propyl]isoindoline-1,3-dione; 5mmol 2-[3-(p-tolylthio)propyl]isoindoline-1,3-dione The ketone and 20 mmol of hydrazine hydrate were refluxed overnight in 20 mL of ethanol, filtered with suction, spin-dried, and then separated by column chromatography to obtain 3-(p-tolylthio)-1-propylamine.

[0091] The reaction formula is as follows:

[0092]

[0093] The compound prepared 1 H nuclear magnetic resonance (400MHz) detection, the solvent is CDCl 3 , see the test results image 3 , the results show that the prepared compound is consistent...

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PUM

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Abstract

The invention discloses a preparation method of an aromatic compound containing sulfydryl, and applications of the aromatic compound in preventing HIV. The aromatic compound possesses a structure represented by formula I. Host self conservative cell protein PCAF BRD is taken as an action target by the aromatic compound, the aromatic compound is capable of avoiding drug resistance caused by high-degree variation of HIV, and inhibiting HIV multiplication activity preferably, and can be used for preparing drugs used for inhibiting HIV multiplication, and toxicity on human normal lymphocyte is relatively low.

Description

technical field [0001] The present invention relates to the field of biochemistry, and more specifically relates to a compound and its preparation method and application. Background technique [0002] AIDS, Acquired Immunodeficiency Syndrome, is an infectious disease caused by human immunodeficiency virus (HIV) infection. HIV is a virus that attacks the body's immune system. It takes the most important T4 lymphoid tissue in the human immune system as an attack target, destroys T4 lymphoid tissue in large quantities, and produces highly fatal internal failure. This virus spreads throughout the region for life, destroys the immune balance of people, and makes the human body a carrier of various diseases. [0003] HIV itself does not cause any disease, but when the immune system is destroyed by HIV, the human body loses the opportunity to replicate immune cells due to low resistance, and is infected with other diseases, resulting in various co-infections and death. [0004] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C321/28C07C319/20C07C319/02C07C323/12C07C323/25C07C323/09C07C327/16C07C205/57C07C201/12A61K31/10A61K31/135A61K31/235A61K31/255A61P31/18
Inventor 汪志勇张胜李丽君鲍亚捷王斌
Owner UNIV OF SCI & TECH OF CHINA