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Dipeptide boronic acids consisting of beta amino acids, ester compounds and preparation methods and uses thereof

A compound and amino technology, applied in the field of preparation of novel peptide boronic acid and its ester compounds, can solve the problems of neuropathy, heavy economic burden on patients, etc.

Active Publication Date: 2010-06-23
NANJING SIMCERE DONGYUAN PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Such an expensive drug is a very heavy financial burden for many patients
Moreover, current clinical data show that these drugs also have more side effects, such as diarrhea, vomiting, and neuropathy.

Method used

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  • Dipeptide boronic acids consisting of beta amino acids, ester compounds and preparation methods and uses thereof
  • Dipeptide boronic acids consisting of beta amino acids, ester compounds and preparation methods and uses thereof
  • Dipeptide boronic acids consisting of beta amino acids, ester compounds and preparation methods and uses thereof

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Embodiment Construction

[0060] Synthesis of the first part of the compound

[0061] The preparation of the compound of the present invention can be carried out according to the following process:

[0062] One, the preparation of compound (II)

[0063]

[0064] 1. Preparation of β-amino acid methyl ester hydrochloride II-2:

[0065] Dissolve the β-amino acid II-1 without any protective group in anhydrous methanol, and add SOCl dropwise to the reaction system at -5°C 2 , slowly raised to room temperature, reacted for 1 hour, and then refluxed for 1 hour. The solvent was distilled off, and the obtained solid was recrystallized (methanol / ether) to obtain the hydrochloride salt of β-amino acid methyl ester (Formula II-2).

[0066] 2. Preparation of amino-protected β-amino acid methyl ester II-3:

[0067] Method a:

[0068] The amino-protecting agent Pg and the β-amino acid methyl ester II-2 prepared in 1 were dissolved in THF, and N-methylmorpholine and a suitable peptide condensation reaction rea...

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Abstract

The invention discloses boronic acids and ester compounds, preparation methods and uses thereof. The compounds have the structure of a formula I, wherein R1 is substituted or non-substituted C1 to C10 alkyl, C3 to C6 naphthene base or heterocyclic alkyl, phenyl, naphthyl or indolyl, and R2 is substituted or non-substituted C1 to C10 alkyl, C3 to C 6 naphthene base or heterocyclic alkyl, benzyl, naphthylmethyl or indole methyl; Z1 or Z2 are respectively and independently hydroxyl, C1 to C10 alkyl, C1 to C10 alkoxy or aryloxy, or B, Z1 and Z2 together form a heterocyclic group containing N, S or O; and Pg is substituted or non-substituted C1 to C10 alkanoyl, C1 to C10 of alkoxyacyl, aromaticacyl or heterocyclic acyl containing N, S or O. The compounds of the invention can be applied in the preparation of proteasome inhibitors or antineoplastic agents.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a preparation method of a novel peptide boronic acid and its ester compound and its application in pharmacodynamics. Background technique [0002] At present, malignant tumors are still one of the major diseases that threaten people's lives. Although the treatment of cancer has made great progress, it has not been able to treat cancer fundamentally. Although the currently marketed anticancer drugs have certain curative effects, most of them are cytotoxic drugs with serious toxic and side effects. Therefore, how to start from effective tumor targets to study targeted new anticancer drugs has become a top priority for medical workers. [0003] The Ubiquitin-Proteasome Pathway (UPP) can regulate the level of proteins involved in cell cycle control. This pathway has an important relationship with the pathogenesis of cancer, cardiovascular and cerebrovascular diseases and d...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07F5/04A61K31/69A61P35/00A61P43/00
Inventor 朱永强吴刚赵欣朱新荣李月杰马玉恒殷晓进
Owner NANJING SIMCERE DONGYUAN PHARM CO LTD
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