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4-(4-aminobenzene sulfonamide) phenylacetic acid derivative and preparation method and application thereof

A technology of aminobenzenesulfonamide group and phenylacetic acid, which is applied in the fields of chemistry and pharmacy, can solve the problems of hypoglycemia, elevated cholesterol level, can not effectively improve diabetes lipid metabolism disorder, etc., and achieves the effect of high yield

Inactive Publication Date: 2014-03-19
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many kinds of hypoglycemic drugs with different therapeutic effects, they generally cannot effectively improve the lipid metabolism disorder associated with diabetes, and there are problems such as side effects of long-term use. For example, biguanide drugs can easily cause gastrointestinal reactions and lactic acidosis. Sulfonylureas can easily cause hypoglycemia, and long-term use of thiazolidinediones can cause weight gain, edema, elevated low-density lipoprotein cholesterol levels, and liver toxicity

Method used

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  • 4-(4-aminobenzene sulfonamide) phenylacetic acid derivative and preparation method and application thereof
  • 4-(4-aminobenzene sulfonamide) phenylacetic acid derivative and preparation method and application thereof
  • 4-(4-aminobenzene sulfonamide) phenylacetic acid derivative and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1, the preparation of intermediate IM1

[0051]

[0052] Add p-aminophenylacetic acid (4-APA), K 2 CO 3 and an appropriate amount of water, stir to dissolve, cool in an ice bath, add dropwise an acetone solution of p-acetamidobenzenesulfonyl chloride (ASC), 4-APA, K 2 CO 3 The molar ratio of ASC and ASC is 1:2.1:1.2-1.5. After the dropwise addition, the ice bath is removed, the reaction is stirred at room temperature, and the reaction progress is monitored by thin layer chromatography (TLC). After the reaction, the acetone was removed by rotary evaporation under reduced pressure to obtain a light yellow turbid liquid, which was filtered with suction, the filter cake was washed with water, and dried to obtain a crude product. Put the crude product in 20mL 2N KOH, stir and dissolve for 0.5h, filter with suction, wash the filter residue with water, combine the lotion with the filtrate, cool in an ice bath, slowly add concentrated HCl dropwise, a large amou...

Embodiment 2

[0056] Embodiment 2, the preparation of intermediate IM2

[0057]

[0058] Add IM1 and a certain concentration of KOH solution to the reaction flask in sequence, stir to dissolve, raise the temperature to 60-65°C and control the temperature to stir the reaction, and monitor the reaction progress by TLC. After the reaction was completed, cool in an ice bath, slowly add concentrated HCl dropwise, a large amount of solids precipitated, adjust the pH=4 to 5 (subject to no more solid precipitation), filter with suction, wash the filter cake with water, and dry at room temperature to obtain the crude product . The crude product was dispersed with 0.2N HCl, filtered with suction, the filter cake was washed with water, and dried in vacuum to obtain the intermediate IM2. Some experimental conditions and results are shown in Table 2.

[0059] Preparation conditions and results of Table 2IM2

[0060]

[0061] IM2 4-(4-aminobenzenesulfonamido)phenylacetic acid: m.p.121.4~122.7℃; ...

Embodiment 3

[0062] Embodiment 3, the preparation of 4-(4-aminobenzenesulfonamido) phenylacetic acid derivative TM1

[0063]

[0064] Add IM2 and K to the reaction flask in sequence 2 CO 3 0.70g (5mmol) and 8mL of acetone, stir to dissolve, cool in an ice bath, add acid chloride R dropwise 3 After COCl was added, the reaction was stirred under temperature control, and the reaction progress was monitored by TLC. After the reaction, acetone was removed by rotary evaporation, an appropriate amount of water was added to stir, and 2N HCl was added dropwise to adjust the pH to 2-3 (subject to the fact that no solids were precipitated), left to stand, suction filtered, the filter cake was washed with water, and dried at room temperature to obtain Crude. The crude product was recrystallized from mixed solvents such as DCM-petroleum ether and EA-petroleum ether (the sample for analysis was further purified by column chromatography) to obtain compound TM1. Part of the experimental conditions...

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Abstract

The invention discloses a 4-(4-aminobenzene sulfonamide) phenylacetic acid derivative with a general formula shown as the accompanying drawing. The 4-(4-aminobenzene sulfonamide) phenylacetic acid derivative structurally comprises a benzene sulfonamide structural unit and a phenylacetic acid structural unit. According to in-vitro antidiabetic activity determination results, the compounds have a certain activity of stimulating peroxisome proliferator activated receptors (PPARs). The PPAR relative stimulating rate of partial compounds (taking pioglitazone as a reference) exceeds 58 percent and reaches 81.79 percent high. The compounds can be used for preparing antidiabetic drugs and can also be used as pilot molecules of novel antidiabetic drugs for deep research. The invention additionally provides a method for preparing the compounds through multiple lines, the method is simple and efficient and the yield is high.

Description

technical field [0001] The invention belongs to the fields of chemistry and pharmacy, and relates to a class of p-aminophenylacetic acid derivatives, a preparation method of the derivatives and an application in the field of pharmacy. Background technique [0002] Diabetes mellitus (DM), a complex endocrine and metabolic disorder, has become one of the three non-communicable chronic diseases with the highest morbidity and mortality in the world. In 2010, the number of diabetic patients in China ranked first in the world. At present, commonly used oral drugs for the treatment of type 2 diabetes in clinical practice are mainly divided into four categories according to their modes of action: (1) sugar regulators, such as α-glucosidase inhibitors and aldose reductase inhibitors; (2) insulin secretion accelerators, such as sulfonylureas and glitinides; (3) insulin sensitizers, such as biguanides and thiazolidinediones (TZDs); (4) incretin potentiators, such as Glucagon-like pep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/44C07D303/38A61K31/63A61P3/10
Inventor 杨大成晏菊芳杨艳陈欣范莉杨龙
Owner SOUTHWEST UNIV
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