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Homoserine lactone compounds as well as preparation methods and application thereof

A technology of ester compounds and homoserine, which is applied in organic chemistry, drug combination, and pharmaceutical formulation, can solve the problems of difficult access to chiral raw materials, limited in-depth research, and complicated synthetic routes, so as to improve quorum sensing inhibition activity and yield. The effect of high yield and simple preparation method

Active Publication Date: 2015-02-18
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthesis and structural modification of such compounds have been reported in the literature, their further in-depth research is limited by the shortcomings of complex synthetic routes or the difficulty of obtaining the required chiral raw materials.

Method used

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  • Homoserine lactone compounds as well as preparation methods and application thereof
  • Homoserine lactone compounds as well as preparation methods and application thereof
  • Homoserine lactone compounds as well as preparation methods and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] (S,E)-2-((4-(3-(4-chlorophenyl)acryloyl)phenyl)amine)-N-(2-carbonyltetrahydrofuran-3-yl)acetamide

[0054] Add 10.12g (67.7mmol) of L-methionine to a mixed solution of 200mL of water and 30mL of methanol. After mixing well, slowly add about 5.1mL (1.2eq) of methyl iodide under airtight conditions. The reaction was stirred overnight until the system became clear and transparent. After concentrating under reduced pressure, add NaHCO dropwise to the system 3 Aqueous solution (5.69g is dissolved in 80mL water), after dropping, the system is transferred to an oil bath and heated to reflux for about 6 hours. After the TLC detection reaction is complete, the solvent is evaporated under reduced pressure to obtain a bright yellow oil, acetone and ethanol ( V:V=1:9) recrystallized to obtain a large amount of white solid. Dissolve the white solid in 100 mL of hydrochloric acid (6mol L -1 ) solution, heated to reflux for about 10h, the system was wine red, and TLC detected that ...

Embodiment 2

[0059] (S,E)-N-(4-(3-(4-chlorophenyl)acryloylphenyl)-2-((2-carbonyltetrahydrofuran-3-yl)amino)acetamide

[0060] Add 10.12g (67.7mmol) of L-methionine to a mixed solution of 200mL of water and 30mL of methanol. After mixing well, slowly add about 5.1mL (1.2eq) of methyl iodide under airtight conditions. The reaction was stirred overnight until the system became clear and transparent. After concentrating under reduced pressure, add NaHCO dropwise to the system 3 Aqueous solution (5.69g is dissolved in 80mL water), after dropping, the system is transferred to an oil bath and heated to reflux for about 6 hours. After the TLC detection reaction is complete, the solvent is evaporated under reduced pressure to obtain a bright yellow oil, acetone and ethanol ( V:V=1:9) recrystallized to obtain a large amount of white solid. Dissolve the white solid in 100 mL of hydrochloric acid (6mol L -1 ) solution, heated to reflux for about 10h, the system was wine red, and TLC detected that t...

Embodiment 3

[0118] The target compound synthesized by the present invention is tested for activity against two tumor cell lines of human liver cancer cell HePG2 and human esophageal cancer cell EC-109, and the test result shows that the derivative has certain antitumor activity.

[0119] 1. Experimental method:

[0120] (1) Preparation of 1640 culture medium: under sterile conditions, take an appropriate amount of serum-free RPMI 1640 medium, add it to 10% fetal bovine serum and shake evenly; then add double antibody (streptomycin 100 μg / mL and penicillin 100 μg / mL) and shake well. Store in the refrigerator at 4°C for later use.

[0121] (2) Preparation of PBS buffer salt: Weigh 1.56g Na2HPO4, 0.2g KH2PO4, 0.2g KCl, 8.0g NaCl, dissolve in 950mL ultrapure water, stir and dissolve with a clean glass rod, and then add ultrapure Dilute to 1000mL with water. Place it in a clean infusion bottle, insert a needle into the bottle stopper, sterilize at 121°C for 20 minutes under high temperature...

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Abstract

The invention discloses homoserine lactone compounds as well as preparation methods and application thereof, relates to two series of compounds, i.e., N-acyl homoserine lactone and N-acetyl homoserine lactone, as well as preparation methods thereof, belonging to the chemical field of medicines, and in particular relates to a type of novel homoserine lactone compounds as shown in a chemical general formula described in the specification. According to the invention, mother nucleus of homoserine lactone is modified and an acyl side chain and a chalcone compound having large conjugated groups are introduced, thus improve quorum sensing inhibiting activity of the compound. The route preparation method is simple and easy to implement, and yield is high and reaches more than 70%.

Description

technical field [0001] The invention relates to the field of pharmaceutical compounds, in particular to a novel homoserine lactone compound, a preparation method and application thereof. Background technique [0002] Traditional antibiotics are aimed at interfering with important life processes such as bacterial cell wall synthesis, folic acid synthesis, protein production, and DNA synthesis, and achieve the purpose of anti-infection by directly killing or inhibiting the growth of microorganisms. Under the selection of this survival pressure, bacteria are prone to mutations and will develop resistance to antibiotics. However, bacteriostatic agents developed based on the bacterial quorum sensing system will not interfere with the normal physiological activities of bacteria, but only inhibit the quorum sensing of bacteria by blocking the expression of their harmful genes, thereby making them lose their ability to cause disease, so they are regarded as antibacterial agents. Ne...

Claims

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Application Information

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IPC IPC(8): C07D307/33A61K31/341A61P35/00A61P31/04
CPCC07D307/33
Inventor 吴春丽陈新丽朱凯蒋月明梁永喜赵峻洁李杰明吴冠连任常忠李攀
Owner ZHENGZHOU UNIV
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