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5-iodine-4-sulfur-2'-deoxyuridine, and derivatives and synthetic method thereof

A technology of deoxyuridine and its synthesis method, which is applied in the direction of preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problem of inability to selectively act on cancer cells, etc., and achieve the improvement of industrial application prospects, wide application prospects, and purity high effect

Active Publication Date: 2012-09-19
DALIAN UNIV
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Problems solved by technology

Therefore, the new derivatives of 2'-deoxy-5-iodo-4-thiouridine can selectively act on cancer cells, while the photosensitizing reagents used in phototherapy in the prior art do not accumulate in the nucleus and cannot selectively act on cancer cells. Acts on cancer cells

Method used

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  • 5-iodine-4-sulfur-2'-deoxyuridine, and derivatives and synthetic method thereof
  • 5-iodine-4-sulfur-2'-deoxyuridine, and derivatives and synthetic method thereof
  • 5-iodine-4-sulfur-2'-deoxyuridine, and derivatives and synthetic method thereof

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Embodiment 1

[0055] Embodiment 1: A kind of synthetic method of the synthetic method of 2'-deoxy-5-iodo-4-thiouridine comprises the following steps:

[0056] (1) Synthesis of 3', 5'-O-dioxoacetyl-5-iodo-2'-deoxyuridine [III] by acetylation, the reaction formula is as follows:

[0057]

[0058] In a 100ml three-strength flask, add 1.00g (2.82mmol) 5-iodo-2'-deoxyuridine [II], 15ml anhydrous pyridine, and after it is fully dissolved, add 3.0ml (32mmol) acetic anhydride, in ice React under bath conditions for 16h, remove the solvent under reduced pressure, then add 10ml each of dichloromethane and benzene, remove the solvent under reduced pressure, and then add 20ml of dichloromethane to remove the solvent under reduced pressure. The crude product was dissolved in 250ml of dichloromethane, then added with 80ml of saturated sodium bicarbonate, and extracted three times with dichloromethane. The organic layer was dried over excess anhydrous sodium sulfate, filtered, and the solvent was remo...

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Abstract

The invention discloses 5-iodine-4-sulfur-2'-deoxyuridine, and derivatives and a synthetic method of the 5-iodine-4-sulfur-2'-deoxyuridine. The synthetic method comprises the steps of using 5-iodine-2'-deoxyuridine as main raw material, treating by using acetic anhydride under a certain conditions to obtain 3', 5'-O-dioxo acetyl-5-iodine-2'-deoxyuridine, reacting under the action of phosphorus pentasulfide, then, introducing ammonia to saturated methanol solution, stirring and deprotecting at the room temperature to obtain 5-iodine-4-sulfur-2'-deoxyuridine. According to the invention, the compound and the derivatives have greatest absorption with the ultraviolet spectrum at 345 nm and stronger UVA photosensitivity. Therefore, the compound provided by the invention is a new basic base sulfur-containing nucleosides compound, can alternatively acts on cancer cells and has potential medical value; besides, the synthetic method provided by the invention has the advantages of simple reaction conditions, accessible raw material, low cost, high product yield, high purity and high efficiency.

Description

technical field [0001] The invention relates to a compound and its derivatives which have the maximum absorption at 345nm in the ultraviolet spectrum and are highly sensitive to UVA light. The invention also relates to a synthesis method of the above-mentioned substance. Background technique [0002] World Health Organization (WHO) officials warned at the 2008 International Oncology Annual Meeting held in Atlanta, USA that by 2010 cancer will replace cardiovascular disease as the disease with the largest number of deaths in the world. The previously dreaded cardiovascular diseases (stroke and myocardial infarction) will take a backseat to the second place. From August 18th to 21st, 2010, the 21st World Anti-Cancer Congress organized by the International Union Against Cancer was held in China for the first time. Minister of Health Chen Zhu said in his speech at the opening ceremony that cancer has become the number one cause of death among urban and rural residents in China....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/073C07H19/20C07H1/00
CPCY02P20/55
Inventor 张晓辉银鸿雁
Owner DALIAN UNIV
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