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Benzoic acid derivative as well as preparation and hypoglycemic application thereof

A methanol and drug technology, applied in the field of benzoic acid derivatives and its preparation, can solve problems such as toxic and side effects

Active Publication Date: 2014-06-25
INST OF MICROBIOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The α-glucosidase inhibitors currently used in the market are mainly acarbose, voglibose, miglitol, etc., but it is worth noting that these inhibitors currently used have brought different degrees of Toxic side effects, such as gastrointestinal side effects, urticaria, liver dysfunction, cardiac system risk, etc.

Method used

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  • Benzoic acid derivative as well as preparation and hypoglycemic application thereof
  • Benzoic acid derivative as well as preparation and hypoglycemic application thereof
  • Benzoic acid derivative as well as preparation and hypoglycemic application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Preparation of compound shown in embodiment 1, formula I and compound shown in formula II

[0061] 1. Strain activation

[0062] Stereum hirsutum THG20 was inoculated onto a PDA medium plate and cultured at 25°C in the dark for 7 days (mycelia covered the entire plate).

[0063] PDA medium (natural pH): Potato 200g, glucose 20g, agar powder 18g, dilute to 1L with distilled water.

[0064] 2. Seed cultivation

[0065] The mycelium in step 1 was transferred to liquid PDB medium, and cultured at 28°C and 180rmp in the dark for 7 days to obtain a seed culture solution.

[0066] PDB medium (natural pH): 200g potatoes, 20g glucose, distilled water to 1L.

[0067] 3. Solid fermentation culture

[0068] Take 5ml of the seed culture solution obtained in step 2 and inoculate it into a solid medium (one solid medium is installed in each 500ml Erlenmeyer flask, set up 10 Erlenmeyer flasks, and each solid medium is composed of 80g of indica rice and 100ml of water), 25 Cultivat...

Embodiment 2

[0091] Embodiment 2, the in vitro inhibitory alpha-glucosidase activity test of the compound obtained in embodiment 1

[0092] Test sample solution: 7 compound solutions prepared in Example 1 with final concentrations of 100.0 μM, 50.0 μM, 25.0 μM, 12.5 μM, 6.25 μM, and 3.13 μM (dissolved in a small amount of DMSO, diluted with distilled water to the corresponding concentration , to control the final volume fraction of DMSO <0.1%); and as a positive control, acarbose solutions with final concentrations of 4000 μM, 1000 μM, 250 μM and 62.5 μM (dissolved in a small amount of DMSO, diluted with distilled water to the corresponding concentration, control Final volume fraction of DMSO <0.1%).

[0093] Take 25 μL of the above test sample solutions with different concentrations, add 25 μL α-glucosidase aqueous solution (concentration: 0.2 U / mL) and 175 μL phosphate buffer solution (50 mM, pH7.0). After the mixed solution was left at room temperature for 10 minutes, 25 μL of 4-nitrob...

Embodiment 3

[0100] Embodiment 3, the animal experiment of the compound obtained in embodiment 1

[0101] 1. Construction of rat model of type II diabetes in rats

[0102] 1. Experimental animals

[0103] Take 50 male wistar rats and feed them adaptively for one week: room temperature 18-25°C, humidity 50-60%, light-dark cycle 12 / 12 hours, free to eat and drink; give standard rat feed.

[0104] 2. Type II diabetes rat model modeling experiment

[0105] Blank group: 10 wistar male rats were given normal standard rat diet.

[0106] Model group: 90 Wistar male rats were given high-sugar and high-fat diet.

[0107] Feed the rats in both the blank group and the model group for 4 weeks, fast for 8 hours, take the tail vein blood of the rats on the 29th day to measure the fasting blood glucose, and inject streptozotocin 45mg / kg body weight intravenously, and feed After feeding for 72 hours and fasting for 8 hours, the rat tail vein blood was taken to measure fasting blood glucose.

[0108] T...

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Abstract

The invention discloses a benzoic acid derivative as well as preparation and a hypoglycemic application thereof, the benzoic acid derivative is a compound represented by a formula I and a formula II, and in the formula I, R1 and R2 is any one of the following a)-d): a) R1=CH3, R2=COOH; b) R1=CH3, R2=COOCH3; c) R1=CH3, R2=CHO; and d) R1=CH2OH, R2=CH2OCH3; in the formula II, the R1 is any one of the following e)-g): e) R1=CH2CH2CH2COOH; f) R1=CH(COOH)CH(CH3)CH2CH3; and g) R1=CH(COOH)CH2(CH3)CH3. The experiment proves that the compound provided by the invention has strong activity for inhibiting alpha-glucosidase, and obviously reducing the blood glucose level of type II diabetes mellitus rat. The compound provided by the invention and the pharmaceutical salt thereof provide material basis for developing an innovative drug for treating and / or preventing type II diabetes mellitus, developing an innovative hypoglycemic drug for inhibiting alpha-glucosidase and developing food and functional healthcare products with above functions, and has potential huge social benefit and economic benefit.

Description

technical field [0001] The invention relates to benzoic acid derivatives and their preparation methods and applications, in particular to two types of 7 kinds of benzoic acid derivatives, their preparation methods and their applications as alpha-glucosidase inhibitors. Background technique [0002] Type 2 diabetes has become a non-communicable disease that seriously affects human health worldwide. There are more than 20 million diabetic patients in my country, of which nearly 90% are type 2 diabetes, and it appears multiple and younger, which seriously threatens national health. . Insulin in patients with type II diabetes is in a relatively deficient state, so its treatment can use other drugs without completely relying on insulin. At present, the main methods of treating diabetes are insulin therapy and oral administration of hypoglycemic drugs such as sulfonylureas and biguanides. However, insulin therapy is expensive, while other types of drugs have the characteristics of...

Claims

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Application Information

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IPC IPC(8): C07C69/84C07C69/86C07D209/34A61K31/235A61K31/405A61P3/10A23L1/30C12P7/62C12P17/10C12R1/645A23L33/10
CPCC07C69/84C07C69/86C07D209/46C12P7/62C12P17/10
Inventor 刘宏伟王波涛马轲齐秋月韩俊杰
Owner INST OF MICROBIOLOGY - CHINESE ACAD OF SCI
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