Shikonin piperazine acid ester derivatives as well as synthetic method and application thereof

A technology of shikonin piperazine acid and its derivatives, applied in organic chemistry, antibacterial drugs, etc., can solve the problems of shikonin toxicity, side effects, low water solubility, etc., and achieve obvious antibacterial activity and low toxicity and side effects

Active Publication Date: 2017-10-31
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Since Shicaoning is a fat-soluble natural product, there is a problem of low water solubility, and it was found in follow-up studies that Shicaoning has the disadvantages of toxic and side effects

Method used

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  • Shikonin piperazine acid ester derivatives as well as synthetic method and application thereof
  • Shikonin piperazine acid ester derivatives as well as synthetic method and application thereof
  • Shikonin piperazine acid ester derivatives as well as synthetic method and application thereof

Examples

Experimental program
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Effect test

example 1

[0015] Example 1: Preparation of Shikonin piperazine ester derivatives

[0016] Under the condition of ice bath, add shikonin, corresponding carboxylic acid, refined dichloromethane and catalyst in sequence in a 50mL round bottom flask, TLC detects that the reaction is complete, and separates by thin plate chromatography to obtain the corresponding shikonin piperazinate derivatives .

[0017] The physicochemical data of the corresponding compounds are as follows:

[0018] Compound 1: yield 61%; 1 H NMR (300MHz, CDCl 3 )δ12.58(s, 1H), 12.39(s, 1H), 7.18(s, 2H), 7.15-7.08(m, 1H), 7.08-6.94(m, 2H), 6.92(d, J=8.8Hz , 2H), 6.12(dd, J=6.9, 4.9Hz, 1H), 5.10(t, J=7.2Hz, 1H), 3.80(s, 3H), 3.56(s, 2H), 3.48(s, 4H) , 3.27(s, 4H), 2.69-2.60(m, 1H), 2.58-2.50(m, 1H), 1.69(s, 3H), 1.59(s, 3H). MS(ESI): 521.2([M+ H] + ).

[0019] Compound 2: yield 63%; 1 H NMR (300MHz, CDCl 3 )δ12.57(s, 1H), 12.36(s, 1H), 7.26(d, J=16.3Hz, 1H), 7.16(s, 2H), 7.10(s, 1H), 6.82(s, 2H), 6.67(d, J=7.6Hz...

example 2

[0050] Example 2: Application of Formula I Shikonin Carboxylate Derivatives

[0051] Gram-positive bacteria B.subtilis, S.aureus and Gram-negative bacteria E.coli, P.aeruginosa strains were used as detection strains, and MTT colorimetry was used as the detection method, through the detection of formula I class shikonin piperazine acid The research on the antibacterial activity of ester derivatives found that this kind of novel structural derivatives has obvious antiproliferative activity against Gram-positive bacteria. The results are shown in Table 1.

[0052] The shikonin carboxylate derivatives of the present invention can be prepared into antibacterial drugs.

[0053] Table 1 Antibacterial activity of shikonin carboxylate derivatives

[0054]

[0055]

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Abstract

The invention belongs to the technical field of chemical pharmaceuticals and in particular relates to shikonin piperazine acid ester derivatives and an application thereof in an antibacterial aspect. Corresponding carboxylic acids are connected with shikonin through synthetic means so as to obtain corresponding ester derivatives. In-vitro antibacterial activity study proves that the shikonin piperazine acid ester derivatives have excellent inhibitory activities on Gram negative bacteria.

Description

1: Technical field [0001] The invention belongs to the technical field of chemical pharmacy, and in particular relates to the preparation of a shikonin piperazine ester derivative and its application in antibacterial aspects. Two: background technology [0002] Bacterial infection used to be the number one "killer" that endangered human health. After a long dark age, the invention of antibiotics brought hope to human beings. However, since the first generation of antibiotics - penicillin officially came out to the present, in just over 70 years, more and more antibiotics that were once the "panacea" for treating bacterial infections are failing. Bacteria's resistance to antibiotics seriously endangers the treatment of infectious diseases, especially the increasingly serious multidrug resistance of bacteria is a global medical and social problem, which has attracted extensive attention from biomedical researchers. Therefore, the research and development of novel structural a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/15C07D295/26A61P31/04
CPCC07D295/15C07D295/26
Inventor 杨永华王小明王子振邱寒月孙文学吴逊
Owner NANJING UNIV
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