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7-(N-(2-pyridyl)sulfonamide or amido)-N-hydroxy heptamide derivative, its preparation method and application thereof

A technology based on hydroxyheptanamide and sulfonamide, which is applied in the field of biomedicine, can solve problems such as complex pathogenesis, and achieve a good effect of inhibiting HDAC activity

Inactive Publication Date: 2012-10-17
SHANGHAI MEDICILON INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the complexity of the etiology and pathogenesis of tumors, and the current lack of understanding of the relationship between epigenetic modifications and tumors and the mechanism of epigenetic modifications regulating genes, histone acetylation and deacetylation modifications are important factors in tumor epigenetics. Therefore, strengthening the research on the correlation between various HDACi alone and in combination with tumorigenesis and development will help to deepen the understanding of epigenetic mechanisms, and then guide the treatment of tumors and the development of new drugs

Method used

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  • 7-(N-(2-pyridyl)sulfonamide or amido)-N-hydroxy heptamide derivative, its preparation method and application thereof
  • 7-(N-(2-pyridyl)sulfonamide or amido)-N-hydroxy heptamide derivative, its preparation method and application thereof
  • 7-(N-(2-pyridyl)sulfonamide or amido)-N-hydroxy heptamide derivative, its preparation method and application thereof

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preparation example Construction

[0051] (1) Preparation of formula (I) compound:

[0052]

[0053]

[0054] Wherein, A is carbonyl or sulfone; R is alkyl, aryl, substituted aryl or azaaryl; X is bromine or chlorine.

[0055] In step a, reactant formula (II) amine compound and formula (III) halogenated compound directly react without solvent, (III) halogenated compound can be slightly excess, for example formula (II) amine compound and formula (III) halogenated compound The molar ratio of the substituted compound may be 1:1 to 1:1.1, preferably 1:1.05. The base can be used in an equimolar amount to the halogenated compound (III), and the base used includes, but is not limited to, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate, preferably sodium carbonate or potassium carbonate. In step a, the reaction temperature may be 100-130° C., and the reaction time may be 4-6 hours. After the reaction, the compound of general formula (IV) is obtained by separation and purificat...

Embodiment 1

[0063] Example 1: 7-(3-chloro-N-(2-pyridyl)benzenesulfonamido)-N-hydroxyheptanamide

[0064]

[0065] Step a: In a 50ml flask, 2-aminopyridine (7.67g, 81.6mmol) was dissolved in 7-chloro-N-methoxyheptanamide (18.192g, 81.6mmol), then potassium carbonate (11.26g, 81.6 mmol). Then the temperature was raised to 120° C. for 4 hours. After the reaction is completed, cool to room temperature, add methanol to the reaction liquid to dissolve, filter, spin the filtrate, and separate the white solid intermediate product 7-(N-(2-pyridyl)amino)-N-formaldehyde by silica gel column chromatography. Oxyheptanamide (3.558g), yield: 18.5%.

[0066] Step b: 7-(N-(2-pyridyl)amino)-N-methoxyheptanamide (3.558g, 15.08mmol) and 3-chlorobenzenesulfonyl chloride (4.8g, 22.62mmol) were dissolved in Add N,N-diisopropylethylamine (2.92 g, 22.62 mmol) to 75 ml of dichloromethane solution, and heat to reflux for 24 hours. The reaction was cooled to room temperature, the reaction solution was spin-dr...

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Abstract

The invention relates to a 7-(N-(2-pyridyl)sulfonamide or amido)-N-hydroxy heptamide derivative, its preparation method and an application thereof, and provides a compound, the structure of which is as shown in the general formula (I) which is defined in the specification. The compound provided by the invention has a good activity for inhibiting HDAC and will be hopefully developed into a novel antitumor drug.

Description

technical field [0001] The invention belongs to the field of biomedicine, and specifically relates to a new compound for inhibiting histone deacetylase family members, as well as a preparation method and application of the compound. Background technique [0002] The number of deaths due to tumor diseases worldwide is second only to the number of deaths from cardiovascular and cerebrovascular diseases, and there is currently no effective drug. Chemotherapy drugs can easily lead to severe toxic and side effects due to the lack of selection of targets, which greatly restricts the clinical effect. Therefore, the development of broad-spectrum, low-toxic and targeted anti-tumor drugs has become the focus of most attention. In the 1990s, histone acetyltransferase (histone acetyltransferase, HAT) and histone deacetylase (histone deacetylase, HDAC) were elucidated at the molecular level (Luger et al., Nature, 389, 251-260, 1997 ). Humans have been found to have 18 HDACs. In 1997,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/76C07D213/75C07D213/82A61K31/63A61K31/444A61K31/4402A61P35/00
Inventor 薛建付国良陈慧平陈春麟李伟蒋维平谢立成蔡振一葛啸虎
Owner SHANGHAI MEDICILON INC
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