Flavone sulphonamide derivative with anti-cancer activity as well as preparation method and application thereof

A flavone sulfonamide and ketone sulfonamide technology, which is applied in the fields of organic active ingredients, medical preparations containing active ingredients, organic chemistry, etc., can solve the problems of no obvious tumor specificity and low anti-tumor activity in anti-tumor activity

Active Publication Date: 2015-04-22
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Based on the above research findings, it is assumed that flavonoids can be spliced ​​by introducing sulfonamide groups, and the activity may be greatly improved. However, there are few literatures on the synthesis of flavone sulfonamides, and the antitumor activity of the reported compounds is relatively low, and their Antitumor activity without apparent tumor specificity

Method used

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  • Flavone sulphonamide derivative with anti-cancer activity as well as preparation method and application thereof
  • Flavone sulphonamide derivative with anti-cancer activity as well as preparation method and application thereof
  • Flavone sulphonamide derivative with anti-cancer activity as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 18

[0052] Preparation of Example 18-p-Hydroxyphenethylsulfonyl-5-hydroxyl-7-methoxyflavone

[0053] (1) Weigh 0.508g (2mmol) of 5,7-dihydroxyflavone into a 250mL three-necked round-bottomed flask, add 100mL of acetone; at the same time weigh 0.552g of anhydrous potassium carbonate, dissolve it in 10mL of distilled water, and slowly add it to 5, In the acetone solution of 7-dihydroxyflavone, after stirring at room temperature for half an hour, add 148 μL iodomethane, react at 40°C for 8 hours, concentrate the reaction solution under reduced pressure, wash with distilled water, and obtain 0.520 g of light yellow 5-hydroxy-7-methoxy flavonoids. (2) Take 13.2 mL of chlorosulfonic acid in a three-necked flask, cool to -5°C, add 2 mmol of 5-hydroxy-7-methoxyflavone in batches and stir for 3 hours. After the reaction is completed, pour the reaction solution into ice water in batches , extracted 3 times with ethyl acetate, combined the ethyl acetate extracts, concentrated and dried unde...

Embodiment 28

[0054] Preparation of Example 28-Benzylaminosulfonyl-5-hydroxyl-7-methoxyflavone

[0055] The synthesis method was the same as in Example 1, wherein the p-hydroxyphenethylamine in step (3) was replaced by benzylamine (1.1 mmol), and the target compound was synthesized as a light brown solid powder with a yield of 40.7%. The results of instrumental analysis of the compound structure: 1 H-NMR (CDCl 3 ,400MHz)δ13.91(1H,s,5-OH),8.21(2H,d,J=8.0Hz,H-2′,H-6′),7.56(3H,m,H-3′,H -4′,H-5′),7.13-7.19(5H,m,ArH),6.82(1H,s,H-3),6.32(1H,s,H-6),5.46(1H,t,J =6.0Hz,NH),4.24(2H,d,J=6.0Hz,CH 2 ),3.90(3H,s,CH 3 O). 13 C-NMR (CDCl 3 ,100MHz) δ182.4, 166.1, 165.3, 162.6, 155.3, 135.9, 132.5, 130.3, 129.3, 128.5, 128.0, 127.9, 127.2, 107.6, 105.4, 105.1, 95.9, 57.2, 48.1. MS m / z[M+H] + : 438.25.

Embodiment 38

[0056] Example 38 - Preparation of p-methylanilinesulfonyl-5-hydroxyl-7-methoxyflavone

[0057] The synthesis method is the same as in Example 1, wherein p-hydroxyphenethylamine in step (3) is replaced by p-methylaniline (1.1 mmol), and the target compound is synthesized as light yellow solid powder with a yield of 61.3%. The results of instrumental analysis of the compound structure: 1 H-NMR (CDCl 3 ,400MHz)δ13.94(1H,s,5-OH),8.18(2H,dd,J=7.6,1.6Hz,H-2′,H-6′),7.52-7.58(3H,m,H- 3′,H-4′,H-5′),7.11(1H,s,NH),6.99(2H,dd,J=6.0,2.8Hz,H-3′′,H-5′′),6.98 (2H,dd,J=6.0,2.8Hz,H-2'',H-6''),6.77(1H,s,H-3),6.42(1H,s,H-6),4.11(3H ,s,CH 3 O),2.21(3H,s,CH 3 ). 13 C-NMR (CDCl 3 ,100MHz) δ182.4, 166.5, 165.3, 163.0, 156.1, 135.4, 134.0, 132.5, 130.3, 130.0, 129.3, 127.2, 121.2, 106.0, 105.4, 105.2, 95.9, 57.4, 20.8. MS m / z[M+H] + : 438.25.

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Abstract

The invention discloses a flavone sulphonamide derivative with anti-cancer activity as well as a preparation method and an application thereof. The derivative is a compound with a structural formula shown as a general formula I or pharmaceutically acceptable sodium salt, potassium salt, sulphate, hydrochloride, a halogen compound or an ester compound of the compound shown in the general formula I; the derivative is simple and practicable in preparation method and low in cost; and the derivative disclosed by the invention has good anti-tumour activity, obvious inhibition effect to a HepG2 human liver cancer cell strain and good practical value and application prospect in the filed of preparation of anti-tumour drugs.

Description

technical field [0001] The invention relates to a pharmaceutical compound, in particular to a flavone sulfonamide derivative with anticancer effect and its preparation method and application. Background technique [0002] Flavonoids are widely distributed in nature and have a wide variety of quantities, and have a wide range of pharmacological activities, such as anti-tumor, anti-oxidation, anti-virus, detoxification and liver protection. At the same time, sulfonamide compounds also have a wide range of pharmacological activities, such as diuresis, anti-thyroid, anti-diabetes, anti-hypoglycemia, and treatment of cataracts. In recent years, a large number of sulfonamide compounds with anti-tumor activity have been reported [1], some of which have entered the stage of clinical trials. Based on the above research findings, it is assumed that flavonoids can be spliced ​​by introducing sulfonamide groups, and the activity may be greatly improved. However, there are few literatur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30A61K31/352A61P35/00A61P1/16
Inventor 李悦青赵伟杰宋其玲张祥芳李贞
Owner DALIAN UNIV OF TECH
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