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Preparation method of ATPase (adenosine triphosphatase) inhibitor compound

A technology of inhibitors and synthetic methods, applied in the direction of organic chemistry, etc., can solve problems such as the description of synthetic methods, and achieve the effect of improving the reaction yield

Inactive Publication Date: 2014-03-12
NEW MATERIAL INST OF SHANDONG ACADEMY OF SCI
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Problems solved by technology

[0005] However, in all reports, there is no response to 2-[4-(5-ethylfuran)-6-(2,2,6,6-tetramethylpiperidin-4-amino)]pyridyl-4- The synthetic method of methylphenol is described in detail

Method used

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  • Preparation method of ATPase (adenosine triphosphatase) inhibitor compound
  • Preparation method of ATPase (adenosine triphosphatase) inhibitor compound
  • Preparation method of ATPase (adenosine triphosphatase) inhibitor compound

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Embodiment 1

[0027] Step 1: Compound Ⅱ Synthesis

[0028] 2-Hydroxy-5-methyl-acetophenone (15 g, 56.7 mmol) was dissolved in DMF ( N,N -dimethylformamide, 30 mL), add imidazole (7.73 g, 113.4 mmol, 2.0 eq). At room temperature, slowly add a dichloromethane solution of TBSCl (tert-butyldimethylsilyl chloride, 10.3 g, 68.0 mmol, 1.2 eq dissolved in 10 mL of dichloromethane) dropwise, and continue the reaction at room temperature for 5-6 h. The reaction was completed, poured into water (150 mL), extracted with dichloromethane (2 × 50 mL), combined organic phase, saturated NaHCO 3 solution (50 mL), washed with saturated brine (50 mL), anhydrous Na 2 SO 4 dried and concentrated to give the compound Ⅱ , the yield is 90%.

[0029] Step Two: Compound Ⅳ Synthesis

[0030] Add the compounds sequentially to the reaction vial Ⅱ (15.9 g, 60 mmol), compound Ⅰ (8.94 g, 72 mmol, 1.2 eq), compound Ⅲ (7.14 g, 72 mmol, 1.2 eq) and ammonium acetate (18.5 g, 240 mmol, 4.0 eq), adding toluene (100...

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Abstract

The invention belongs to the technical field of chemical medicine, and particularly relates to a novel synthetic method of an ATPase inhibitor compound. The invention provides a novel synthetic route of an ATPase inhibitor 2-[4-(5-ethyl furan) -6-(2, 2, 6, 6-tetramethyl piperidine-4- amino)] pyridyl-4-methylphenol. The preparation method has the positive effects that reaction conditions are mild, raw materials are cheap and easy to obtain, and the method is suitable for industrial scale production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and relates to a novel RecA ATPase inhibitor compound 2-[4-(5-ethylfuran)-6-(2,2,6,6-tetramethylpiperidine-4-amino )] The synthetic method of pyridyl-4-methylphenol. Background technique [0002] 2-[4-(5-Ethylfuran)-6-(2,2,6,6-tetramethylpiperidin-4-amino)]pyridyl-4-methylphenol is a RecA ATPase inhibitor agent with antimicrobial activity ( Current Chemical Genomics , 2010, 4 , 34-42). The CAS number of 2-[4-(5-ethylfuran)-6-(2,2,6,6-tetramethylpiperidin-4-amino)]pyridinyl-4-methylphenol is 503105-88- 2. The structural formula is: [0003] [0004] Multi-substituted pyridine compounds have attracted extensive attention due to their good biological activities. The synthesis of such molecules is reported in hundreds of documents and patents. But only a few documents, Pakistan Journal of Scientific and Industrial Research , 1977, 20(3), 139-49, Archiv der Pharmazie (Weinheim,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14
CPCC07D405/14
Inventor 韩哲朱英王绪科刘玉庆
Owner NEW MATERIAL INST OF SHANDONG ACADEMY OF SCI
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