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1,3,4-oxadiazole derivative containing glucosamine fragment as well as synthetic method and use of derivative

A synthesis method and technology of glucose, applied in the directions of sugar derivatives, sugar derivatives, sugar derivatives preparation, etc., can solve the problems of harsh reaction conditions, many by-products, unfriendly environment, etc.

Inactive Publication Date: 2014-12-03
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some of the above methods are commonly used, most of them have one or more disadvantages, such as: harsh reaction conditions, long cyclization time, more by-products, expensive catalysts, narrow use range of substrates, and unfriendly to the environment, etc.

Method used

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  • 1,3,4-oxadiazole derivative containing glucosamine fragment as well as synthetic method and use of derivative
  • 1,3,4-oxadiazole derivative containing glucosamine fragment as well as synthetic method and use of derivative
  • 1,3,4-oxadiazole derivative containing glucosamine fragment as well as synthetic method and use of derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1, a glucosamine-based 1,3,4-oxadiazole, its molecular formula is as follows: Formula III:

[0044]

[0045] Wherein, the R is selected from CH 3 -, C 4 h 9 -, C 6 h 5 -, 4-CH 3 C 6 h 4 -, 3-CH 3 C 6 h 4 -,2-CH 3 C 6 h 4 -, 4-CH 3 OC 6 h 4 -, 3,4-di-CH 3 OC 6 h 4 -, 3-CH 3 OC 6 h 4 -, 4-FC 6 h 4 -, 2,3-di-FC 6 h 4 -, 4-ClC 6 h 4 -, 2-ClC 6 h 4 -, 4-BrC 6 h 4 -, 4-IC 6 h 4 -, 3-IC 6 h 4 -, 4-OHC 6 h 4 -, 4-NO 2 C 6 h 4 -,

[0046] 3-NO 2 C 6 h 4 -, 3-C 6 h 4 N-, 2-C 5 h 3 S-,5-Cl-2-C 5 h 2 S-, 4-( N , N -di-CH 3 )-C 6 h 4 -.

[0047]The 1,3,4-oxadiazole derivatives containing glucosamine fragments of the present invention, as a class of novel compounds, have higher inhibitory activity on urease. The following is the urease activity experiment process and its results. Urease activity test method: urease activity was detected using the method of Tanaka et al. (Tanaka T, Kawase M, Tani S. (2003). Urease inh...

Embodiment 2

[0049] Embodiment 2, a kind of synthetic method of the 1,3,4-oxadiazole derivative containing glucosamine fragment as described in embodiment 1, its steps are as follows:

[0050] (1) the compound shown in formula I N -(2-Acetamido-3,4,6 - Tris-O-acetyl-2-deoxy- β -D-pyranose)- N' -amide thiosemicarbazide, p-toluenesulfonyl chloride and organic base were dissolved in tetrahydrofuran and reacted at 20°C for 3 hours, the reaction solution was distilled under reduced pressure, and purified by silica gel column chromatography to obtain the compound shown in formula II N -(2-Acetylamino-3,4,6-tri-O-acetyl-2-deoxy- β -D-pyranose)-5-substituted-1,3,4-oxadiazol-2-amine; the molar ratio of the compound shown in formula I, p-toluenesulfonyl chloride and organic base is 1:1:1; The organic base is pyridine or triethylamine;

[0051]

[0052] R in formula I and formula II is the same as R in formula III;

[0053] (2) React the compound represented by formula II in a mixed solution...

Embodiment 3

[0054] Embodiment 3, a kind of synthetic method of the 1,3,4-oxadiazole derivative containing glucosamine fragment as described in embodiment 1, its steps are as follows:

[0055] (1) the compound shown in formula I N -(2-Acetamido-3,4,6 - Tris-O-acetyl-2-deoxy- β -D-pyranose)- N' -amide thiosemicarbazide, p-toluenesulfonyl chloride and organic base were dissolved in tetrahydrofuran and reacted for 10 hours at 65°C. The reaction solution was distilled under reduced pressure and purified by silica gel column chromatography to obtain the compound shown in formula II. N -(2-Acetylamino-3,4,6-tri-O-acetyl-2-deoxy- β -D-pyranose)-5-substituted-1,3,4-oxadiazol-2-amine; the molar ratio of the compound shown in formula I, p-toluenesulfonyl chloride and organic base is 1: 1.5: 2.1; The organic base is pyridine or triethylamine;

[0056]

[0057] R in formula I and formula II is the same as R in formula III;

[0058] (2) React the compound represented by formula II in a mixed s...

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Abstract

The invention discloses a 1,3,4-oxadiazole derivative containing a glucosamine fragment as well as a synthetic method of the 1,3,4-oxadiazole derivative containing the glucosamine fragment and a use of the derivative. The 1,3,4-oxadiazole derivative containing the glucosamine fragment is a novel compound, and has relatively high inhibitory activity on urease. The synthetic method disclosed by the invention is a convenient, high-yield and efficient method; paratoluensulfonyl chloride is taken as a cyclization reagent, the operation is simple and safe, the environmental pollution is small, the scope of application is wide and the yield is high.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a 1,3,4-oxadiazole derivative containing a glucosamine fragment, and also relates to a synthesis method and application thereof. Background technique [0002] 1,3,4-Oxadiazole is a commonly used pharmacodynamic active group due to its easy metabolism in vivo and the ability to associate in the form of hydrogen bonds, and also exhibits many biological activities such as: anti Inflammatory, antibacterial, anticancer, anticonvulsant, analgesic and diuretic, etc. At present, the antihypertensive drugs that have been marketed, such as thiodazosin (I) and nesadil (II) and the antibiotic drug Furamizole (III) all contain oxadiazole active groups in their molecular structures (the structural formula is shown below). Some 1,3,4-oxadiazole-containing compounds also act as inhibitors of HIV integrase and angiogenesis. [0003] [0004] D-glucosamine (2-amino-2-deoxy-D-glucose) is obtai...

Claims

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Application Information

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IPC IPC(8): C07H17/00C07H1/00A61K31/7056
Inventor 刘玮炜李曲祥程峰昌张强霍云峰殷龙
Owner HUAIHAI INST OF TECH
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