Ring opening myrtle ketone analogue as well as preparation method and application thereof to antibacterial medicines

An antibacterial drug, the technology of aurinone, which is applied in antibacterial drugs, resistance to vector-borne diseases, and pharmaceutical formulations, etc.

Active Publication Date: 2016-08-17
GUANGZHOU LEADER BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the fact that there is no satisfactory anti-MRSA infection drug at present, it is particularly urgent to develop a new anti-MRSA infection drug, which has great scientific significance, broad market prospects and potential economic value.

Method used

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  • Ring opening myrtle ketone analogue as well as preparation method and application thereof to antibacterial medicines
  • Ring opening myrtle ketone analogue as well as preparation method and application thereof to antibacterial medicines
  • Ring opening myrtle ketone analogue as well as preparation method and application thereof to antibacterial medicines

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the preparation method of open-ring myrtone analogue:

[0028] The synthesis process of the ring-opened myrtone analog of the present invention is as follows:

[0029]

[0030] Use phloroglucinol and alkyl acid chloride under the catalysis of methanesulfonic acid or aluminum trichloride, obtain the precursor compound 6 in the formula (5) through Friedel-Crafts acylation reaction, wherein R is H, C 1 -C 15 Straight chain, branched chain and cycloalkyl or aromatic groups containing structures such as benzene rings; another precursor compound 10 can be carried out under alkaline conditions by using acetylphloroglucinol 6b as raw material to carry out C-methyl and then quickly obtained through protonic acid-catalyzed reverse Claisen condensation and Knoevenagel condensation; the obtained precursor compound 6 and compound 10 (α, β-unsaturated ketone) are further promoted to undergo Michael addition under basic conditions. reaction, the target product 11 ca...

Embodiment 2

[0114] Embodiment 2: the anti-MRSA activity evaluation of compound

[0115] In this embodiment, the minimum inhibitory concentration (MIC) of the anti-MRSA activity of the sample will be determined by the resazurin chromogenic method. In the test, the 96-well plate dilution titer technique will be used to simultaneously determine the minimum inhibitory concentration (MIC) of various substances. First, mix 7.5 mL of indicator solution (100 μg / mL resazurin aqueous solution) with 5 mL of the bacteria solution to be tested (10 8 CFU / mL) and mix well, and add 100 μL of mixed bacterial solution to all test wells in columns 1 to 8. Then add 100 μL of the DMSO solution (64 μg / mL) of the sample compound 11a-11u to be tested into each well of the first column in sequence, and after uniform mixing, take out 100 μL of the solution and transfer it to the corresponding well of the second column, and use the same Method for doubling dilutions to column 8. Finally, put the orifice plate wi...

Embodiment 3

[0120] Embodiment 3: the anti-SA activity evaluation of compound

[0121] In this embodiment, the minimum inhibitory concentration (MIC) of the anti-SA activity of the sample will be determined by the resazurin chromogenic method. In the test, the 96-well plate dilution titer technique will be used to simultaneously determine the minimum inhibitory concentration (MIC) of various substances. First, mix 7.5 mL of indicator solution (100 μg / mL resazurin aqueous solution) with 5 mL of the bacteria solution to be tested (10 8 CFU / mL) and mix well, and add 100 μL of mixed bacterial solution to all test wells in columns 1 to 8. Then add 100 μL of the DMSO solution (64 μg / mL) of the samples 11a-11u to be tested into the wells of the first column in sequence, and after uniform mixing, take out 100 μL of the solution and transfer it to the corresponding wells of the second column, and use the same Method doubling dilutions to column 8. Finally, put the orifice plate with the sample a...

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PUM

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Abstract

The invention discloses a ring opening myrtle ketone analogue as well as a preparation method and application thereof to antibacterial medicines. The structure of the ring opening myrtle ketone analogue is shown in a formula (1) in the specification, wherein in the formula (1), R is H, a C1-C15 straight chain or branched chain or naphthenic base or an aromatic group. The ring opening myrtle ketone analogue has obvious activity of resisting Methicillin-resistant Staphylococcus aureus (MRSA), Staphylococcus aureus, Bacillus cereus, B.subtilis, B.thuringiensis or Escherichia coli, so the ring opening myrtle ketone analogue can be used for preparing bacterial infection resistant medicines and is especially applied to preventing and treating clinically common MRSA infectious diseases.

Description

Technical field: [0001] The invention belongs to the field of synthetic medicinal chemistry, and in particular relates to an open-ring myrtone analogue, a preparation method thereof and an application in antibacterial drugs. Background technique: [0002] Methicillin-resistant Staphylococcus aureus (MRSA), since it was first discovered by Jevons in England in 1961, has accounted for an increasing proportion of Staphylococcus aureus infections, and has been increasing since the mid-1980s The 1%-5% of the infection has rapidly increased to the current 60%-70%, and the degree of infection has become more and more serious. It has become one of the important pathogenic bacteria for hospital and community infection. At present, MRSA is resistant to commonly used antibiotics in clinic, and has become a multi-drug resistant pathogen that seriously threatens human health. Its infection is almost all over the world, and it can be transmitted between livestock and human beings, leading...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/757C07C49/83A61K31/122A61P31/04
CPCC07C49/757C07C49/83Y02A50/30
Inventor 谭海波邱声祥刘洪新赵丽云龚亮徐志防
Owner GUANGZHOU LEADER BIO TECH
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