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Cytarabine derivatives and purposes thereof in resisting cancers and tumors

A technology of cytarabine and derivatives, applied in the medical field, can solve the problems of inability to treat liver cancer, failure of N4 amino metabolism, slow activation process, etc.

Active Publication Date: 2013-07-31
高峰 +1
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Problems solved by technology

[0006] Cytarabine (see attached figure 1 ) generally cannot be used for the treatment of liver cancer, the reason is that when its cytidine skeleton structure enters the liver, its N4 amino group is metabolized and causes toxicity; on the other hand, the O5 hydroxyl group on its glycoside structure must be phosphorylated and activation, and this activation process is too slow in the liver

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  • Cytarabine derivatives and purposes thereof in resisting cancers and tumors
  • Cytarabine derivatives and purposes thereof in resisting cancers and tumors
  • Cytarabine derivatives and purposes thereof in resisting cancers and tumors

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Embodiment Construction

[0072] The synthetic routes of some representative cytarabine derivatives of the present invention are listed below. Other similar cytarabine derivatives of the present invention are synthesized by the same or similar method.

[0073] Synthetic route 1:

[0074]

[0075] Synthesis of cytarabine derivative 1 (Scheme 1): cytarabine (1.0 g, 4 mmol) and acetic anhydride (0.9 ml, 4.8 mmol) were dissolved in methanolic MeOH (500 ml). The reaction mixture was heated to reflux for 4 hours. The reaction solution was purified by column chromatography (silica gel, developer: dichloromethane / methanol=10 / 1) to obtain cytarabine derivative 1 (84.6 mg), with LC (UV 254nm) purity>95%. LC-MS m / z 286[M+H] + (molecular formula C 11 h 15 N 3 o 6 , molecular weight 285). 1 H NMR (600MHz, DMSO-d 6 )δ10.84(s, 1H), 8.06(d, 1H), 7.18(d, 1H), 6.05(d, 1H), 5.50(d, 1H), 5.49(d, 1H), 5.06(t, 1H ), 4.06(m, 1H), 3.94(m, 1H), 3.83(m, 1H), 3.61(t, 2H), 2.10(t, 3H).

[0076] Synthetic route 2:

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Abstract

The invention relates to cytarabine prodrug derivatives which are novel prodrug derivatives designed through chemically modifying N4 and O5 positions and can prevent N4 amino being metabolized to lose efficacies and result in toxicity; and in addition, the cytarabine prodrug derivatives let O5 hydroxy be easily phosphorylated for activation. The cytarabine prodrug derivatives have the advantages of increasing bioavailability, reducing multiple drug resistance (multi-targeting design technique) and increasing solubility and ester dissolution. The invention also provides a synthesis method of the cytarabine prodrug derivatives, a cytarabine prodrug derivative preparation and a preparation method thereof in detail and proves the purposes of the cytarabine prodrug derivatives at the aspect ofresisting cancers and tumors through a great amount of experimental data.

Description

technical field [0001] The present invention relates to the field of medical technology, in particular to a novel cytarabine derivative and its synthesis route, and the present invention also relates to a preparation of a cytarabine derivative and a preparation method thereof, a cytarabine derivative and a preparation thereof Use in anti-cancer and anti-tumor. Background technique [0002] Cancer is currently the most important disease that endangers human life and health. The existing methods for treating cancer mainly include: surgical resection, radiotherapy, chemotherapy or a combination of these methods. Chemotherapy is widely used and has been used in the treatment of many different types of cancer. However, most of the anticancer drugs used in chemotherapy are limited to delaying the progression of cancer so as to prolong the patient's life, and it is difficult to achieve the purpose of curing. Although the pathogenesis of various cancers is different, they are actu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/09C07H19/10C07H19/06C07H1/00A61K31/7068A61P35/00A61P35/02
Inventor 高峰徐峻
Owner 高峰
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