Hydroxycinnamic acid amide compounds, methods of making and antibacterial uses thereof

By synthesizing magnolamide compounds, the problem of poor inhibitory effects of existing antibiotics on MRSA and biofilms was solved, achieving highly efficient antibacterial activity and biofilm inhibition against Staphylococcus aureus and MRSA, while enhancing the antibacterial activity of polymyxin B.

CN122212966APending Publication Date: 2026-06-16NANHUA UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
NANHUA UNIV
Filing Date
2026-03-26
Publication Date
2026-06-16

AI Technical Summary

Technical Problem

Existing antibiotics have limited inhibitory effects on methicillin-resistant Staphylococcus aureus (MRSA) and biofilm-forming bacteria. The problem of resistance to polymyxin antibiotics is serious, and there is a need to develop new compounds to enhance antibacterial activity and biofilm inhibition capabilities.

Method used

We designed and synthesized magnolamide compounds by introducing different substituted amide groups to create compounds with excellent antibacterial activity, and combined them with polymyxin B to enhance antibacterial activity against drug-resistant bacteria.

Benefits of technology

The magnolamide compounds exhibited excellent antibacterial activity against Staphylococcus aureus and MRSA, significantly inhibited biofilm formation, and enhanced the antibacterial activity of polymyxin B, demonstrating good in vivo safety and anti-infective activity.

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Abstract

The application discloses a kind of magnolol amide compounds and its preparation method and antibacterial application.The compound is with magnolol as parent nucleus, structure is modified by introducing different substituted amide side chain and is obtained, and its structure is as shown in general formula (I).The magnolol amide compound can be used to prepare antibacterial drugs, especially can be used to prepare anti-staphylococcus aureus, methicillin-resistant staphylococcus aureus, biofilm-related infection treatment drug and polymyxin antibiotic sensitizer.Therefore, the magnolol amide compound has good application prospect as antibacterial drug or antibacterial adjuvant further development, while yield is higher, synthesis method is simple, easy to obtain, suitable for amplification production, and is expected to be further developed as clinical natural product antibacterial drug.(I)
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Claims

1. A magnolamide compound, the general structural formula of which is shown in formula (I): （Ⅰ）； in, R 1 Selected from R 2 Selected from -H or , where R 3 R 4 Independently selected from phenyl, said phenyl may optionally be substituted with halogen, -OH, -CN, C1-C3 alkyl or C1-C3 alkoxy.

2. The magnolamide compound according to claim 1, characterized in that, The phenyl group is optionally substituted with -F, -Cl, -Br, -OH, -CN, -CH3 or -OCH3, and the substituent is one, two or three.

3. The magnolamide compound according to claim 1, characterized in that, The R 3 R 4 Independently selected from one of the following groups: 。 4. The magnolamide compound according to claim 1, characterized in that: The R 1 = R 2 =-H, where R 3 Selected from one of the following groups: ； Or, the R 1 = R 2 = , where R 3 =R 4 Selected from one of the following groups: 。 5. The method for preparing the magnolamide compound according to any one of claims 1-4, characterized in that, Includes the following steps: Among them, R 3 As described in any one of claims 1-4; (1) The hydroxyl group of magnolol at C-4' was protected by iodocyclization to obtain intermediate 2; (2) Nitrate intermediate 2 to obtain intermediate 3; (3) The intermediate 3 is reduced to obtain the intermediate 4; (4) Intermediate 4 is deiodinated and ring-opened to obtain intermediate 5; (5) Under the action of a catalyst, intermediate 5 is reacted with different acyl chloride intermediates (II) to obtain unilaterally substituted magnolamide derivatives, which are the magnolamide compounds. Alternatively, it may include the following steps: Among them, R 3 As described in any one of claims 1-4; (1) By nitration reaction, magnolol is simultaneously nitrated at the C-3 and C-3' positions to obtain intermediate 6; (2) The intermediate 6 was reduced to obtain the intermediate 7; (3) Under the action of a catalyst, intermediate 7 is reacted with different acyl chloride intermediates (II) to obtain bilaterally substituted magnolamide derivatives, which are the magnolamide compounds.

6. The method for preparing the magnolamide compound according to claim 5, characterized in that, The preparation method of the acyl chloride intermediate (II) includes the following steps: reacting benzoic acid and salicylic acid containing different substituents with oxalyl chloride through a nucleophilic reaction to obtain different acyl chloride intermediates (II).

7. The use of the magnolamide compounds according to any one of claims 1-4 in the preparation of antibacterial drugs.

8. The application according to claim 7, characterized in that, The antibacterial drug can inhibit Staphylococcus aureus, Escherichia coli, and methicillin-resistant Staphylococcus aureus.

9. The use of the combination of the magnolamide compound according to any one of claims 1-4 and polymyxin B in the preparation of a drug for inhibiting polymyxin-resistant Gram-negative bacteria.

10. The application according to claim 9, characterized in that, The aforementioned magnolamide compounds can enhance the antibacterial activity of polymyxin B against polymyxin-resistant Gram-negative bacteria.