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2-(N-(3-quinolyl) sulfamide or amide)-N-glycolamide derivative, and preparation method and applications thereof

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

Inactive Publication Date: 2014-07-02
SHANGHAI MEDICILON INC
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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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  • 2-(N-(3-quinolyl) sulfamide or amide)-N-glycolamide derivative, and preparation method and applications thereof
  • 2-(N-(3-quinolyl) sulfamide or amide)-N-glycolamide derivative, and preparation method and applications thereof
  • 2-(N-(3-quinolyl) sulfamide or amide)-N-glycolamide derivative, and preparation method and applications thereof

Examples

Experimental program
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preparation example Construction

[0050] (1) Preparation of the compound of formula (I) of the present invention

[0051] The reaction route of the present invention for preparing the compound of formula (I) is as follows:

[0052]

[0053] Wherein, A is carbonyl or sulfone; R is alkyl, aryl, substituted aryl or azaaryl; X is bromine or chlorine.

[0054] In step a, the reactant, the amine compound of formula (II) and the halogenated compound of formula (III) are directly reacted without a solvent. The halogenated compound of formula (III) may be slightly excessive, for example, the molar ratio of the amine compound of formula (II) to the halogenated compound of formula (III) may be 1:1 to 1:1.1, preferably 1:1.05. Two to four times the molar amount of the base of the halogenated compound of formula (III) can be used. 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 reac...

Embodiment 1

[0061] Example 1: 2-(3-Chloro-N-(3-quinolinyl)benzenesulfonamide)-N-hydroxyacetamide

[0062]

[0063] Step a: In a 50ml flask, dissolve 3-aminoquinoline (5.0g, 52.9mmol) in 7-chloro-N-methoxyacetamide (10.2g, 52.9mmol), then add potassium carbonate (14.6g ,105.8mmol). Then the temperature was raised to 130°C and reacted for 6 hours. After the reaction is finished, cool to room temperature, add methanol to the reaction solution to dissolve, filter, spin-dry the filtrate, and separate the white solid intermediate product 3-(N-(3-quinolinyl)benzenesulfonamido)- by silica gel column chromatography. N-methoxyacetamide (3.32g), yield: 25%;

[0064] Step b: Dissolve 2-(N-(3-quinolinyl)benzenesulfonamido)-N-methoxyacetamide (3.32g, 13.2mmol) and 3-chlorobenzenesulfonyl chloride (5.6g, 26.4 Add N,N-diisopropylethylamine (3.4g, 26.4mmol) to a 60ml N,N-dimethylformamide solution in mmol), heat to 80°C, and react for 16 hours. After the reaction, cool to room temperature, spin dry the rea...

Embodiment 2～12

[0067] The following compounds of Examples 2-12 were prepared by a method similar to that of Example 1 (see Table 1).

[0068] Table 1: The structures of the compounds of Examples 1-12 and their mass (ESI) theoretical and measured values:

[0069]

[0070]

[0071] A salt-forming method commonly used in the art is used to form an acid addition salt, a base addition salt, or a quaternary ammonium salt with the pharmaceutically acceptable acid and base of the compound prepared above. The inorganic acid can be selected from hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid and phosphoric acid; the organic acid can be selected from acetic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, maleic acid, lauric acid, malic acid, fumaric acid, Succinic acid, tartaric acid, methanesulfonic acid, camphor acid, lactic acid, niacin, cinnamic acid, p-toluenesulfonic acid, benzenesulfonic acid, glutamic acid and mandelic acid; inorganic bases can be selected from alkali ...

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Abstract

The invention relates to a 2-(N-(3-quinolyl) sulfamide or amide)-N-glycolamide derivative, and a preparation method and applications thereof. General formula of the derivative is represented by formula (I), and the formula (I) is defined by the patent specification. The derivative possesses excellent inhibiting activity on HDAC, and is hopeful to be used as a targeted drug used for treating tumour.

Description

Technical field [0001] The invention belongs to the field of biomedicine, and specifically relates to a new compound that inhibits members of the histone deacetylase family, and a preparation method and application of the compound. Background technique [0002] Malignant tumor is a common and frequently-occurring disease that seriously endangers human health. According to a study by the World Health Organization (WHO), out of 58 million deaths worldwide in 2005, 7.6 million died of malignant tumors. About 16% of the death toll. The death toll from malignant tumors worldwide is expected to continue to increase. Since the 1970s, the incidence and mortality of cancer in my country have been on the rise. By the 1990s, the cancer mortality rate had risen to 29.42%, and cancer had become the leading cause of death. [0003] HDAC inhibitor (HDAC inhibitor, HDACi), as a new anti-cancer drug with research and development potential, has shown obvious advantages in recent years: (1) It can...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/38A61K31/47A61P35/00
CPCC07D215/38
Inventor 陈春麟李文成吴清泉马玉晴
Owner SHANGHAI MEDICILON INC
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