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Vidarabine and Vidarabine analogues synthesized by air oxidation hydrazine removal method

A compound, hydrazine-based technology, applied in the fields of chemistry and medicine, can solve problems such as high cost, reduced yield, and health hazards of environmental workers

Active Publication Date: 2013-12-25
HENAN NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some of these dehydrazino-based methods use metals, which are not only expensive, but also harmful to the environment and the health of workers, and the problem of heavy metal residues in the product is difficult to solve; some use strong alkalis, which increase the difficulty of operation and reduce the yield. The production cost of sugar adenosine remains high

Method used

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  • Vidarabine and Vidarabine analogues synthesized by air oxidation hydrazine removal method
  • Vidarabine and Vidarabine analogues synthesized by air oxidation hydrazine removal method
  • Vidarabine and Vidarabine analogues synthesized by air oxidation hydrazine removal method

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Add 0.0008g (2mol%) of copper sulfate catalyst, 8-hydrazinoarabinosine (0.075g, 0.25mmol), 3mL of water into a 25mL round-bottom flask, heat to 80℃ in an oil bath, and react for 6 hours, followed by TLC After the reaction is terminated, the solvent is removed in vacuo, and then the target compound arabinosine is obtained by column chromatography with a yield of 87% (yield is based on 8-hydrazinoarab). The product is a white solid.m.p.264-266℃. 1 H NMR(DMSO-d 6 , 400MHz) δ 8.18 (s, 1H), 8.12 (s, 1H), 7.24 (s, 2H), 6.25 (d, J=4.4Hz, 1H), 5.64 (d, J=4.4Hz, 1H), 5.56(t, J=3.6Hz, 1H), 5.13(t, J=4.4Hz, 1H), 4.13(brs, 2H), 3.79-3.76(m, 1H), 3.69-3.61(m, 2H); 13 C NMR(DMSO-d 6 , 100MHz) δ156.3, 152.9, 149.8, 140.8, 118.7, 84.5, 84.0, 76.1, 75.4, 61.3; HRMS calcd for C 10H13 N 5 NaO 4 [M+Na + ]290.0860, found290.0857.

Embodiment 2

[0020] Add 1.1g (2mol%) of copper sulfate catalyst, 8-hydrazinoarabinosine (100g, 0.34mol), 1L of water into a 2L reaction flask, heat the oil bath to 80°C, react for 6 hours, follow the reaction by TLC, After the reaction was terminated, the solvent was removed in vacuo, the activated carbon was decolorized, and then recrystallized with water to obtain the target compound arabinosine with a yield of 77%.

Embodiment 3

[0022] Add 25g (2mol%) of copper sulfate catalyst, 8-hydrazinoarabinosine (1.5Kg, 5mol), 15L of water into a 100L reactor, heat to 80℃, react for 6 hours, follow the reaction with TLC, and terminate the reaction Then, the solvent was removed in vacuo, the activated carbon was decolorized, and then recrystallized with water to obtain the target compound arabinosine with a yield of 70%.

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Abstract

The invention discloses vidarabine and Vidarabine analogues synthesized by an air oxidation hydrazine removal method. a catalyst and a solvent used in the method disclosed by the invention can avoid the problems of heavy metal residues, use of harmful solvents and the like in the existing synthesis, synthetic operations are simplified, the cost is reduced, and the large-scale preparation of the vidarabine and the vidarabine analogues can be realized conveniently.

Description

Technical field: [0001] The invention belongs to the technical field of chemistry and medicine, and specifically relates to the synthesis of adenosine arabinoside and its analogs by an air oxidative dehydrazine method. Background technique: [0002] In 1962, Baker, B.L. and others discovered for the first time that Arabinosine has good anti-tumor activity, and can effectively inhibit viral DNA replication at lower concentrations. Subsequently, the scientists also found that arabinosine has good anti-herpes virus, anti-cytomegalovirus, hepatitis B virus and other activities, and also has a certain effect on acute non-lymphatic leukemia and herpes simplex virus encephalitis. Adenosine arabinoside is used to treat herpes simplex viral encephalitis, and also to treat herpes zoster and varicella infections in immunosuppressed patients. [0003] At present, most of the synthetic methods of arabinosine reported in the literature are chemical synthesis, and the industrialized method is ma...

Claims

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Application Information

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IPC IPC(8): C07D473/00C07D473/40C07D473/32C07H19/19C07H19/16C07H1/00
Inventor 渠桂荣郭海明杨西宁夏然王秀强蔡玉瑛李涛
Owner HENAN NORMAL UNIV
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