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Process for preparing restraining agent for leishmaniasis

A leishmaniasis and inhibitor technology, applied in the chemical field, can solve problems such as lack of broad-spectrum, difficulty in mass production, difficult purification of cyclization products, etc., and achieve the effect of simple operation and separation

Inactive Publication Date: 2008-10-22
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the existing resolution and lysine cyclization methods are not broad-spectrum, only limited to the case of no substituents, and the cyclization products are not easy to purify, therefore, it is difficult to achieve large-scale preparation with the above strategies

Method used

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  • Process for preparing restraining agent for leishmaniasis
  • Process for preparing restraining agent for leishmaniasis
  • Process for preparing restraining agent for leishmaniasis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]Step 1 Synthesis of (R)-tert-Butyl 4-formyl-2, 2-dimethyloxazolidine-3-carboxylate 2

[0032] This compound was prepared directly according to literature methods (Carner, P. et al., J. Org. Chem. 1987, 52, 2361-2364).

[0033] Step 2 Synthesis of (S, E)-tert-butyl 4-(4-(benzyloxy)but-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate 3(R=H)

[0034] In a nitrogen atmosphere and at -78°C, a tetrahydrofuran solution in which compound 2 (2.42g, 10.55mmol) was dissolved was added dropwise to tetrahydrofuran in which 3-benzyloxypropane quaternary phosphine salt (9g, 18.3mmol) was dissolved, and after heating Stir overnight, the reaction system was diluted with water, extracted three times with ethyl acetate, the organic layer was washed three times with saturated brine, anhydrous Na 2 SO 4 After drying and concentration, the crude product was purified by silica gel column chromatography to obtain compound 3 (R=H) (85.0%).

[0035] Step 3 Synthesis of (S)-tert-butyl 4-(4-(benzyl...

Embodiment 2

[0059] Step 2 Synthesis of (S)-tert-butyl-4-((S,E)-4-(benzyloxy)-3-(tert-butyl dimethylsilyloxy)but-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate 3 (R=OTBS)

[0060] In a nitrogen atmosphere and at -78°C, a solution of compound 2 (13 mmol) in tetrahydrofuran was slowly added dropwise to a solution of 1 benzyloxy-2-tert-butyldimethylsiloxypropane quaternary phosphine salt (25 mmol). tetrahydrofuran, warmed up and then stirred overnight. The reaction system was diluted with water, extracted three times with ethyl acetate, the organic layer was washed three times with saturated brine, anhydrous Na 2 SO 4After drying and concentration, the crude product was purified by silica gel column chromatography to obtain compound 3 (R=OTBS) (78.0%).

[0061] Step 3 Synthesis of (S)-tert-Butyl 4-((S)-4-(benzyloxy)-3-(tert-butyl dimethylsilyloxy)butyl)-2,2-dimethyloxazolidine-3-carb-oxylate 4(R=OTBS ).

[0062] Compound 3 (R=OTBS) (3.62 mmol) was dissolved in EtOH (15 mL), and 47 mg of 5...

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PUM

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Abstract

The invention belongs to the chemical field, which relates to a method for preparing leishmaniasis inhibitor. The invention overcomes the shortages of the prior art, and after a key intermediate compound 11 is synthesized with high yield and high electivity by using the cheap and available D-serine as raw material, asymmetric synthesis on marine natural product (S, S)-Ciliatamides A and B with inhibitive activity against the leishmaniasis and Hela cytotoxicity is carried out. Every step of the invention is simple in operation and high in yield; the used reagents are all common reagents which are cheap and easy to get; the preparation method of the used key intermediate is obviously different from synthesis methods of the prior art.

Description

technical field [0001] The invention belongs to the field of chemistry, and relates to an asymmetric synthesis method, in particular to a method for preparing a leishmaniasis inhibitor, in particular to an isolated leishmaniasis and Hela cell with higher inhibitory activity Preparation of deep-sea marine natural products (S,S)-Ciliatamides A and B. Background technique [0002] Leishmaniasis is caused by the obligate intracellular parasite of Leishmania. If the incidence is mild, it can cause digestive tract ulcers, and if the incidence is severe, it is fatal visceral kala-azar (leishmaniasis). At present, the medicines containing pentavalent antimony are the most effective for the treatment of this disease, but their toxic and side effects on the heart are relatively large. In recent years, many research groups around the world have devoted themselves to finding a new low-toxic and highly effective leishmaniasis inhibitor to replace the existing highly toxic pentavalent a...

Claims

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Application Information

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IPC IPC(8): C07D223/12A61P33/02
Inventor 魏邦国魏晋虎孙逊蒲少卫黄伟林国强
Owner FUDAN UNIV
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