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Aspergillomarasmin compound and synthesis method thereof

A technology of amine compound and synthesis method, which is applied in the direction of organic chemical method, chemical instrument and method, preparation of organic compound, etc., can solve the problems of difficult tramamine product, low output, limited source, etc., and achieves mild conditions and simple process Effect

Active Publication Date: 2016-06-08
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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  • Aspergillomarasmin compound and synthesis method thereof
  • Aspergillomarasmin compound and synthesis method thereof
  • Aspergillomarasmin compound and synthesis method thereof

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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Abstract

The invention provides an aspergillomarasmin compound and a synthesis method thereof. Aspergillomarasmin has natural antibacterial activity and can inhibit enzymes (new Delhi metallo-beta-lactamase 1, DNM-1 and the like) in superbacteria, the superbacteria are made to lose the capacity of decomposing antibiotics, and then the superbacteria are killed by the antibiotics. Aspergillomarasmin can serve as a natural antibiotic additive, an extremely good inhibiting effect is achieved on the superbacteria, and wide application prospects are achieved. The synthesis method of the aspergillomarasmin compound comprises the steps that by means of the mode that Garner's aldehyde is sequentially connected with aspartate, and hydroxyl groups are oxidized into carboxy groups respectively after connection every time, the prepared aspergillomarasmin compound with the specific needed chiral structure is prepared. The synthesis method of the aspergillomarasmin compound is simple in process and mild in reaction condition, industrial production can be easily achieved, and aspergillomarasmin compound molecules with the special chiral structure can be selectively synthesized.

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 (AspergillomarasmineA) L-Asparticacid, 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 metalloenzyme New Delhimetallo-β-lactamase1, 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 antib...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07C229/26
CPCY02P20/55C07D263/06C07B2200/07C07C227/18C07C269/06C07D263/04C07C271/22C07C229/26
Inventor 叶元杰郑祥建黄勤儿
Owner XIAMEN BERYL THERAPEUTICS INC
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