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Fatty acylaminoacylcytarabine conjugate, preparation method and application thereof

A technology of fatty amidoacyl cytarabine and fatty amido arabinocytidine, which is applied in sugar derivatives, drug combinations, pharmaceutical formulations, etc., and can solve problems such as low bioavailability, short half-life, and weak transmembrane ability problem to achieve good antitumor activity

Inactive Publication Date: 2011-01-26
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The first technical problem to be solved by the present invention is to overcome the short half-life of the antineoplastic drug cytarabine due to its short half-life, weak transmembrane ability and low bioavailability due to the easy metabolic inactivation of the 4-amino group of cytarabine, and to provide a A fatty amidoacyl cytarabine conjugate, which has the advantages of strong transmembrane ability, high bioavailability, long half-life, and amphiphilicity

Method used

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  • Fatty acylaminoacylcytarabine conjugate, preparation method and application thereof
  • Fatty acylaminoacylcytarabine conjugate, preparation method and application thereof
  • Fatty acylaminoacylcytarabine conjugate, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1 Preparation of decanoyl valine methyl ester (3a)

[0025] Dissolve 0.69g (4mmol) capric acid, 0.91g (4.4mmol) DCC and 0.54g (4mmol) HOBt in cold anhydrous THF, stir in ice bath for 20min and add 0.67g (4mmol) HCl·H-Val-OMe The pH value was adjusted to 8-9 with 0.5 ml of NMM, and the mixture was stirred at room temperature for 1 day. TLC (chloroform / methanol, 20:1) showed that HCl·H-Val-OMe disappeared. Dicyclohexylurea (DCU) was filtered off, the filtrate was concentrated to dryness under reduced pressure, and the residue was dissolved in 20 ml of ethyl acetate. The resulting solution was sequentially treated with 5% NaHCO 3 Aqueous wash, saturated NaCl aqueous solution, 5% KHSO 4 Wash with aqueous solution and saturated aqueous NaCl solution until neutral. Anhydrous Na was used for the ethyl acetate layer 2 SO 4 Dry, filter, and concentrate the filtrate under reduced pressure to give 1.01 g (89%) of the title compound as a colorless solid. Mp.60-62℃; [α...

Embodiment 2

[0026] Example 2 Preparation of decanoylmethionine methyl ester (3b)

[0027] Following the procedure of Example 1, 1.17 g was prepared from 0.69 g (4 mmol) decanoic acid, 0.91 g (4.4 mmol) DCC, 0.54 g (4 mmol) HOBt, 0.8 g (4 mmol) HCl·H-Met-OMe and 0.5 ml NMM (92%) the title compound as a colorless solid. Mp.50-52℃; [α] D 25 20 =-19.5 (c=1.0, methanol); ESI-MS (m / e) 318.0 [M+H] + , 635.1[2M+H] + , 657.1[2M+Na] + .

Embodiment 3

[0028] Example 3 Preparation of decanoyl tyrosine methyl ester (3c)

[0029] Following the procedure of Example 1, 1.09 g was prepared from 0.69 g (4 mmol) decanoic acid, 0.91 g (4.4 mmol) DCC, 0.54 g (4 mmol) HOBt, 0.93 g (4 mmol) HCl·H-Tyr-OMe and 0.5 ml NMM (80%) the title compound as a colorless solid. Mp.27-29℃; [α] D 25 20 =-17.7 (c=1.0, methanol); ESI-MS (m / e) 350.0 [M+H] + , 699.2[2M+H] + .

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Abstract

The invention discloses a conjugate of fatty aminoacyl alexan, preparation and application in anti-tumor thereof. The invention also discloses a pharmacosome of the conjugate of fatty aminoacyl alexan, preparation thereof, and its applicant in anti-tumor and preparation of target medicine material of microemulsion, lipid medicine carrier. In comparison with alexan, the inventive conjugate of fatty aminoacyl alexan has a strong transmembrane ability, high bioavailability, long halflife, and amphipathic nature. It is demonstrated that the inventive compound and pharmacosome have great anti-tumor activity.

Description

technical field [0001] The present invention relates to derivatives of cytarabine, in particular to fatty amidoacyl cytarabine conjugates; the present invention also relates to a preparation method of fatty amido acyl cytarabine conjugates, and preparation of the conjugates into finished medicines The plastid method and the application of the fatty amidoacyl cytarabine conjugate in anti-tumor and the preparation of microemulsion and liposome drug carrier targeted formulation materials belong to the field of biomedicine. Background technique [0002] Many drugs require multiple traversal of biofilms in the body to reach their target sites (organs, tissues, cells, and organelles). Among the many factors that affect the drug transmembrane, the hydrophilic-lipophilic balance or the oil-water partition coefficient are the obvious physical and chemical factors. Drugs with strong water solubility are compatible with body fluids and cannot easily pass through biological membranes c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/067A61K31/7068A61K47/16A61K47/48A61K9/127A61K9/107A61P35/00A61K47/54
Inventor 崔国辉彭师奇赵明刘伯阳
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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