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Phosphate derivative of oxazole compounds and preparation method thereof

A technology of compounds and oxazoles, which is applied in the field of phosphate derivatives and their preparation, can solve the problems of low bioavailability, poor water solubility, and high lipophilicity, and achieve the advantages of simple preparation method, good water solubility, and improved efficiency Effect

Inactive Publication Date: 2008-07-30
OCEAN UNIV OF CHINA
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Problems solved by technology

Oxazole analogs in CA-4 heterocyclic analogs 4-(3,4,5-trimethoxyphenyl)-5-(3-hydroxy-4-methoxyphenyl)oxazole [English name 4 -(3,4,5-trimethoxyphenyl)-5-(3-hydroxy-4-methoxyphenyl)oxazole] has good inhibitory activity on tumor cells, but still has high lipophilicity, poor water solubility and low bioavailability Defects

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  • Phosphate derivative of oxazole compounds and preparation method thereof
  • Phosphate derivative of oxazole compounds and preparation method thereof
  • Phosphate derivative of oxazole compounds and preparation method thereof

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[0010] Oxazole analogue 4-(3,4,5-trimethoxyphenyl)-5-(3-hydroxy-4-methoxyphenyl) of Lamellarin 1C and CA-4 with simple structure and significant antitumor activity ) Oxazole has a certain skeleton similarity in structure, and the oxazole analog of CA-4 is equivalent to replacing the pyrrole ring at the center of the Lamellarin skeleton with an oxazole ring. Therefore, the present invention uses the oxazole analogs of CA-4 to simulate Lamellarins as a lead compound, conducts structural modification, and prepares a highly active compound that inhibits microtubule aggregation and selectively targets endothelial cells. It is meaningful to have novel microtubule-binding anti-tumor drugs with obvious destructive effect on tumor blood vessels.

[0011] In the present invention, the drug molecule is connected with the phosphate group to form a phosphate derivative, which helps the drug molecule to be transported into the cell, and has good stability and a long half-life before enterin...

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Abstract

The invention discloses a phosphate derivative of an oxazole compound. During the preparation, 4-(3,4,5-Trimethoxyphenyl)-5-(3-hydroxyl-4-methoxyl phenyl) oxazole is dissolved into the mixed solvent of acetonitrile and N, N-dimethyl formamide to react with carbon tetrachloride, dimethylin pyridine and dibenzyl phosphoric acid, for preparing benzyl phosphate ester of the oxazole compound; then the benzyl of benzyl phosphate ester is removed by utilizing trimethyl silicon bromide to obtain the phosphoric acid derivative of oxazole; finally, the phosphoric acid derivative of the oxazole reacts with sodium methoxide, lithium hydroxide, potassium hydroxide, ammonia water or calcium acetale, to obtain the phosphate derivative of the oxazole compound. The preparation method is simple, highly effective and universal. The phosphate derivative of the prepared series of oxazole compounds can be applied as antineoplastic medicine inhibiting microtubule assembly and selectively targeting tumor blood vessels and having novel structure.

Description

technical field [0001] The invention relates to a phosphate derivative of an oxazole compound and a preparation method thereof. Background technique [0002] Lamellarins are a large family of polyaromatic alkaloids isolated from sponges and sea squirts in the ocean. Its structure is characterized by the substitution of a pyrrole center by a polyhydroxyl or polymethoxybenzene ring. Studies have shown that Lamellarins have strong cytotoxic activity against a variety of tumor cell lines, but the complexity of its synthesis makes it very difficult to become a drug. [0003] The antineoplastic drug Combretastatin A-4 (abbreviated as CA-4) is a stilbene compound isolated from the South African plant Combretum caffrum, and its ED of P388 cell line 50 The value is 0.0034 μg / mL, the IC of tubulin polymerization inhibitory activity 50 2-3μM. It has a 3,4,5-trimethoxy substituted A ring and a 3-hydroxy 4-methoxy substituted B ring connected by a cis double bond. CA-4 is a new multi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/653A61K31/675A61P35/00
Inventor 李英霞赵育李春霞王鹏李静耿美玉
Owner OCEAN UNIV OF CHINA
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