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A kind of tramamide compound and its synthetic method

A synthesis method and compound technology, applied in chemical instruments and methods, preparation of organic compounds, cyanide reaction preparation, etc., can solve the problems of low yield, difficult tramamine products, limited sources, etc., and achieve simple process and mild conditions Effect

Active Publication Date: 2017-12-15
XIAMEN BERYL THERAPEUTICS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, currently only relying on the isolation and extraction of tramaline from soil microorganisms, the source is limited and the yield is low
In addition, trameramine molecules have a variety of chiral structures, and the antibacterial properties and activities of different chiral structures are different. It is difficult to obtain trameramine with special chiral structures by separating and extracting trameramine from microorganisms. product
At present, there is no synthetic method that is easy to industrialize the yield of tramamide in the prior art

Method used

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  • A kind of tramamide compound and its synthetic method
  • A kind of tramamide compound and its synthetic method
  • A kind of tramamide compound and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] A kind of synthetic method of tramamide compound, synthetic route is as follows:

[0113]

[0114] , including the following steps:

[0115] (1) Dissolve N-Boc-D-serine methyl ester (10g, 45.6mmol, purity 98%) in acetone (165mL), 2,2-dimethoxypropane (50mL, 400mmol) and boron trifluoride ether (0.35 mL, 2.8 mmol) were added sequentially. After stirring at room temperature for 2.5 h, TLC detected that the raw material had reacted. Triethylamine (0.9 mL) was added to quench the reaction, and then the solvent was evaporated under reduced pressure, ether (150 mL) and saturated sodium bicarbonate solution (250 mL) were added to separate the layers. The aqueous phase was extracted with diethyl ether (150 mL×2), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain compound 2 (12.8 g) as a pale yellow oil, which was directly used in the next step. 1HNMR (400MHz, CDCl 3 )δ4.51-4.35(m,1H),4.2...

Embodiment 2

[0130] Adopt the method identical with embodiment 1, synthesize a kind of chiral structure is the trameramine compound of SRS, synthetic route is as follows:

[0131]

Embodiment 3

[0133] Using the same method as in Example 1, a kind of chiral structure is synthesized as a trameramide compound of SSR, and the synthetic route is as follows:

[0134]

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PUM

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Abstract

The invention provides a tramaline compound and a synthesis method thereof. Tramamide has natural antibacterial activity and can inhibit the enzymes in super bacteria (New Delhi metallo-β-lactamase 1, NDM-1, etc.), making it lose the ability to decompose antibiotics, and then kill bacteria by antibiotics. Tramamide can be used as a natural antibiotic additive, which has an excellent inhibitory effect on superbugs and has broad application prospects. The synthesis method of the tramaline compound of the present invention prepares the tramaline compound with a specific desired chiral structure by linking Garner's aldehyde to aspartic acid successively, and oxidizing the hydroxyl group to a carboxyl group after each link. The synthesis method of the trameramide compound of the invention has simple process, mild reaction conditions, easy realization of industrial production, and can selectively synthesize the trameramide compound molecule with special chiral structure.

Description

technical field [0001] The invention relates to the technical field of natural product synthesis, in particular to a tramamide compound and a synthesis method thereof. Background technique [0002] Tramamine (Aspergillomarasmine A) L-Aspartic acid, N-[(2R)-2-[[(2R)-2-amino-2-carboxyethyl]amino]-2-carboxyethyl]-, Cas: 3484-65- 9. Tramamide is a natural product, and tramaline can be extracted from soil microorganisms in the prior art. Tramamide has natural antibacterial activity, can inhibit enzymes in bacteria (New Delhi metallo-β-lactamase 1, NDM-1, etc.), and then kill bacteria, and has excellent inhibitory effect on superbugs. Tramamide can be used as a natural antibiotic additive and has broad application prospects. [0003] But at present, it only relies on the isolation and extraction of tramaline from soil microorganisms, which has limited sources and low yields. In addition, trameramine molecules have a variety of chiral structures, and the antibacterial propertie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/18C07C229/26
CPCY02P20/55
Inventor 叶元杰郑祥建黄勤儿
Owner XIAMEN BERYL THERAPEUTICS INC
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