Alpha-aryl alanine compounds and preparation method thereof

A technology for aryl alanine and compounds, applied in the fields of medicinal chemistry and anti-infection therapeutics, can solve the problems of low reaction yield, long steps, high cost, etc., and achieve the effects of high yield, mild reaction conditions and cheap raw materials

Inactive Publication Date: 2012-07-18
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

α-arylalanine compounds are the key intermediates for the preparation of Fumimycin, but the existing methods have disadvantages such as high cost, long steps, low reaction yield, complicated post-treatment and separation, etc.

Method used

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  • Alpha-aryl alanine compounds and preparation method thereof
  • Alpha-aryl alanine compounds and preparation method thereof
  • Alpha-aryl alanine compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 3-methyl, 3-(N-acetyl)-5-allyloxy-6-methoxybenzofuran lactone;

[0019] To a solution of methyl 2-acetamidoacrylate (429.4 mg, 3 mmol) in 10 mL of dry THF was added 1.58 mL of BF at room temperature 3 ·Et 2 O (6mmol), after stirring for 0.5 hours, add 5 milliliters of 3-methoxy-4-allyloxyphenol (434 mg, 2.4 mmol) in anhydrous tetrahydrofuran solution, continue to react at room temperature for 48 hours, and distill under reduced pressure to remove Remove the solvent, dissolve the residue with an appropriate amount of ethyl acetate, add saturated sodium bicarbonate solution, extract and separate layers, extract the aqueous phase with ethyl acetate three times, combine the organic phases and wash with saturated brine, and wash the obtained ethyl acetate solution with anhydrous sulfuric acid Sodium drying, filtering to remove the desiccant, and the residue obtained after vacuum distillation was separated by silica gel column chromatography (V petroleum ether / V et...

Embodiment 2

[0020] Example 2 3-methyl, 3-(N-acetyl)-5-allyloxybenzofuran lactone:

[0021] To a solution of methyl 2-acetamidoacrylate (72 mg, 0.5 mmol) in 5 mL of dry THF was added 0.26 mL of BF at room temperature 3 ·Et 2 O (0.99 mmol), after stirring for 0.5 hours, add 2 milliliters of 4-allyloxyphenol (60 mg, 0.4 mmol) in anhydrous tetrahydrofuran solution, continue the reaction at room temperature for 48 hours, remove the solvent by distillation under reduced pressure, and the remaining The mixture was dissolved with an appropriate amount of ethyl acetate, then saturated sodium bicarbonate solution was added, the layers were extracted, the aqueous phase was extracted three times with ethyl acetate, the organic phases were combined and washed with saturated brine, the obtained ethyl acetate solution was dried over anhydrous sodium sulfate, filtered Remove the desiccant, and the residue obtained after vacuum distillation is separated by silica gel column chromatography (V petroleum et...

Embodiment 3

[0022] Example 3 2-(N-acetyl)-2[1-(2,4-dihydroxy)phenyl]propanoic acid

[0023] To a solution of methyl 2-acetamidoacrylate (199 mg, 1.39 mmol) in 10 mL of dry THF was added 0.8 mL of BF at room temperature 3 ·Et 2 O (3 mmol), after stirring for 0.5 hours, add 5 milliliters of resorcinol (130 mg, 1.19 mmol) in anhydrous tetrahydrofuran solution, continue the reaction at room temperature for 48 hours, distill off the solvent under reduced pressure, and use an appropriate amount of After ethyl acetate was dissolved, saturated sodium bicarbonate solution was added, and the layers were extracted. The aqueous phase was extracted three times with ethyl acetate. The organic phases were combined and washed with saturated brine. The obtained ethyl acetate solution was dried with anhydrous sodium sulfate, filtered and removed. agent, and the residue obtained after vacuum distillation was separated by silica gel column chromatography (V petroleum ether / V ethyl acetate 1 / 1) to obtain 2-(...

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PUM

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Abstract

The invention relates to alpha-aryl alanine compounds and a preparation method thereof. Alpha-aryl alanine compounds shown as general formulas (I) and (II) are racemate, wherein R1, R2 and R3 shown as general formulas (I) and (II) are expressed as hydrogen atoms, halogen atoms, hydroxyl, substituted or non-substituted alkyl, alkenyl, alkoxy, aryl, aryl alkyl, alkyl or aryl acyl; R4 is expressed as the hydrogen atoms, formoxyl, acetyl, trifluoro-acetyl, benzoyl, phthaloyl, triphenylmethyl, carbobenzoxy, trimethyl silicon carbethoxy, benzyl, 2,4-dimethoxy benzyl, p-methoxy benzyl and diphenyl phosphoryl; and R5 is expressed as the hydrogen atoms, methyl or ethyl. The invention has the advantages that a novel method for preparing the alpha-aryl alanine compounds, which is low in cost of raw materials, mild in reaction conditions and high in yield is provided, and the alpha-aryl alanine compounds can be used as a synthetic intermediate of a peptide deformylase enzyme (PDF) inhibitor.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and anti-infection therapeutics, in particular to a class of α-arylalanine compounds, their synthesis and use in the preparation of PDF inhibitor antibacterial drugs. Background technique [0002] In recent years, due to the abuse of antibiotics, the problem of bacterial drug resistance has become more and more serious. There is an urgent need for more effective new antibacterial drugs with new mechanisms of action, new targets or new structures to replace and supplement them. Peptide deformylase (PDF) is a new type of ideal antibacterial target with high efficiency, low toxicity and broad spectrum. PDF inhibitors play an antibacterial role by inhibiting PDF, which is necessary for bacterial protein synthesis, and are currently the most promising antibacterial drugs. one. The current PDF inhibitors are mainly some peptide inhibitors, while the non-peptide inhibitors are not studied much. Fumi...

Claims

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Application Information

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IPC IPC(8): C07D307/83C07C233/47C07C231/12
Inventor 周志望李伟超汪玢
Owner NANCHANG UNIV
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