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Borane compound that can be used for antibacterial therapy and its preparation method

A technology of borane compound and dodecaborane, which is applied in the field of borane compound and its preparation, can solve limitations and other problems, and achieve the effects of short synthesis path, sensitive drug-resistant bacteria, and mild reaction conditions

Active Publication Date: 2019-04-02
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, dodecaborane compounds have not been explored in the field of antibacterial. This is mainly due to the limited methods of derivatization of dodecaborane at this stage, mostly non-selective halogenation and hydroxylation.

Method used

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  • Borane compound that can be used for antibacterial therapy and its preparation method
  • Borane compound that can be used for antibacterial therapy and its preparation method
  • Borane compound that can be used for antibacterial therapy and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]

[0047] Under the protection of nitrogen, add 6 mL of anhydrous THF to a 20 mL reaction flask containing monoamined dodecaborane (300 mg, 1.1 mmol) and NaH (90 mg, 3.7 mmol) of the structure represented by formula (23), and stir at room temperature for half Hours, the solution no longer bubbling. Then benzoyl chloride (177 mg, 1.3 mmol) was slowly added within half an hour. Then stir at room temperature for half an hour. After the reaction, add water to quench and dilute, then add Et 3 NHCl (303mg, 2.2mol), fully stirred to make the cation exchange complete, the resulting mixture was extracted 7 times with a mixture of dichloromethane and acetonitrile with a volume ratio of 4:1, and the resulting organic phase was MgSO 4 dry. Then it was filtered and the solvent of the obtained filtrate was removed by rotary evaporation. The residue was subjected to silica gel column chromatography (dichloromethane / acetonitrile=4:3) to obtain the compound represented by formula (3) (43...

Embodiment 2

[0049]

[0050] The synthetic method of the compound represented by formula (4) is the same as that of Example 1, except that the acid chloride used is 3,5-dimethylbenzoyl chloride (219mg, 1.3mmol), the product obtained is a white solid, and the yield is : 85%; 1 H{ 11 B)NMR(400MHz,CD 3 CN): δ7.28(s,2H,phenyl H), 7.09(s,1H,phenyl H), 6.21(s,1H,anionic N-H), 3.18(q,J=7.2Hz,12H,cationic N-CH 2 ),2.31(s,6H,methyl H),1.47-0.79(broadoverlapping m,11H,B-H),1.25(t,J=7.4Hz,18H,N-CH 2 CH 3 ); 13 C{ 1 H)NMR(100MHz,CD 3 CN):δ170.0(C=O),139.0,138.9,132.6,125.3(4phenyl signals),47.8(cationic signal),21.2(methyl signal),9.1(cationic signals); 11 B{ 1 H)NMR(128MHz,CD 3 CN):δ-5.1(1B,B-N),-15.3(5B,B-H),-16.5(5B,B-H),-18.8(1B,B-H).HRMS(ESI) calculated for C 9 H 22 B 12 NO - : 290.2891, Found: 290.2864.

Embodiment 3

[0052]

[0053] The synthesis method of the compound represented by formula (5) is the same as that of Example 1, except that the acid chloride used is 2,4,6-trimethylbenzoyl chloride (237mg, 1.3mmol), and the product obtained is a white solid. Yield: 77%; 1 H{ 11 B)NMR(400MHz,CD 3 CN):δ7.81(br,2H,cationic NH), 6.84(s,1.4H,phenyl H of majorisomer), 6.74(s,0.6H,phenyl H of minor isomer),3.09(q,J=7.4Hz ,12H,cationic N-CH 2 ),2.24(s,3H,para CH 3 ),2.21(s,6H,ortho CH 3 ),1.47-0.67(broad overlapping m,11H,B-H),1.21(t,J=7.4Hz,18H,cationic N-CH 2 CH 3 ); 13 C{ 1 H)NMR(100MHz,CD 3 CN):δ176.1(minor isomer of C=O),173.4(major isomer of C=O),139.3(minor isomer of paraphenyl carbon),137.8(major isomer of para phenyl carbon),136.1(C ipso ),135.3(minor isomer of ortho phenyl carbon),134.9(major isomer of ortho phenylcarbon),47.7(cationic signal),21.2(minor isomer of para CH 3 ),21.1(majorisomer of para CH 3 ),20.2(minor isomer of ortho CH 3 ),19.2(major isomer of orthoCH 3 ),9.1(cationic sign...

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Abstract

The invention provides a borane compound used for antibacterial treatment. The borane compound is a dodecaborane substituted amide or a dodecaborane-oxazole. The preparation method comprises: (1) taking a mono-aminated dodecaborane as a raw material and performing an acylation reaction with an acyl chloride compound under the effect of sodium hydride to obtain a dodecaborane substituted amide; and (2) performing oxidative coupling on the dodecaborane substituted amide obtained in the step (1) under the effect of (diacetoxyiodo)benzene to obtain a dodecaborane-oxazole. The invention also provides an application of the borane compound in preparing antibacterial agents. The borane compound has extremely high antibacterial activity on certain Gram negative bacteria, and has a huge prospect.

Description

Technical field [0001] The invention relates to the field of antibacterial drugs, in particular to a borane compound that can be used for antibacterial therapy and a preparation method thereof. Background technique [0002] In recent decades, the emergence and spread of antibiotic-resistant pathogens has accelerated, resulting in a rapid increase in the level of antibiotic resistance. At present, antibiotic resistance of pathogens has become a global public health problem. Therefore, it is very necessary to develop new types of antibacterial compounds. To this end, the World Health Organization (WHO) has listed a global priority list of antibiotic-resistant pathogens to guide the priority development of new antibiotics and effective antibiotic treatments to solve the urgent problem of antibiotic-resistant pathogens. [0003] In recent years, a large number of studies have evaluated the antibacterial activity of existing antibacterial drug derivatives, such as the new fluoroketola...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/05A61K31/69A61P31/04A61P15/00A61P1/00A61P17/00A61P27/02A61P11/00
CPCC07F5/05Y02A50/30
Inventor 西蒙杜特怀勒孙雨吉张江临
Owner ZHEJIANG UNIV
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