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Bean-curd pectin analogue and its use in medicine for preventing depression

A technology of tofufructidine and analogs, which is applied to the tofufructin analogs and their application fields in antidepressant drugs, and can solve the problems of no retrieval, few in-depth studies, etc.

Active Publication Date: 2010-05-19
KUNMING BAKER NORTON PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The research on tofu glucoside was mainly concentrated in the 1980s. In recent years, there have been fewer studies and fewer in-depth studies; at present, there are no reports on the antidepressant structure-activity relationship of tofu glucoside analogues at home and abroad.

Method used

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  • Bean-curd pectin analogue and its use in medicine for preventing depression
  • Bean-curd pectin analogue and its use in medicine for preventing depression
  • Bean-curd pectin analogue and its use in medicine for preventing depression

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Embodiment 1: Synthesis of O-tetraacetyl tofu glucoside (2a)

[0089] First add 1.0g tofu glucoside (1, 3.5mmol) anhydrous pyridine 2mL into a round bottom flask, stir until completely dissolved, then add 2.5g acetic anhydride (25mmol, excess) dropwise, react at room temperature for 12h, follow up to the reaction by TLC relatively complete. After pouring into 50 mL of ice water and stirring for 30 min, the chloroform layer was separated and extracted. After being washed twice with water, dried over anhydrous magnesium sulfate, the solvent was evaporated to dryness under reduced pressure to obtain a light yellow syrupy substance, which was then recrystallized with 95% ethanol to obtain a white solid powder 2a with a yield of 56%. mp 135-136°C. Anal. Calcd for C 21 h 24 o 11 : C55.75, H5.35; found: C55.79, H5.26; IR (KBr, cm -1 )υ: 1752, 1693, 1601, 1506, 1224, 1157, 1127, 1085, 914, 876; 1 H NMR (CDCl 3 , 300MHz) δ: 9.91(s, 1H, CHO), 7.85(d, J=8.6Hz, 2H, ArH), 7....

Embodiment 2

[0090] Example 2: Synthesis of O-tetrabenzoyl tofu glucoside (2b)

[0091] First add 1.0g (3.5mmol) tofu glucoside and 20mL chloroform into a 50mL three-necked flask. Under stirring at room temperature, 3.5 g (25 mmol) of benzoyl chloride and 4 mL of anhydrous pyridine were successively added through a constant pressure funnel. After reacting at room temperature for 24 hours, TLC tracked that the reaction was relatively complete. 10 mL of methanol was added to terminate the reaction, and after stirring for 10 min, the solvent was spun to dryness to obtain an oily substance. After adding 60 mL of chloroform to dilute, wash with dilute hydrochloric acid aqueous solution, saturated sodium bicarbonate solution, and ice water successively. After the chloroform layer was dried over anhydrous magnesium sulfate, the solvent was evaporated to dryness by rotary evaporation to obtain a light yellow syrupy substance. The white solid powder 2b was separated by silica gel column chromato...

Embodiment 3

[0092] Example 3: Synthesis of O-tetrabenzyl tofu glucoside (2c)

[0093]Add 3.5mmol tofu glucoside, 0.43g (1.33mmol) of tetrabutylammonium bromide, and 7.0g (30mmol) of potassium hydroxide into a 50mL round-bottomed flask filled with 10mL of dry dichloromethane and stir for 10min, then slowly drop Add benzyl bromide (2.4 mL, 17.5 mmol) in 5 mL dichloromethane solution, and stir the reaction at room temperature for 5 h. Finally, the reactant was poured into 50 mL of ice water, the organic phase was extracted and separated, washed twice with water, dried by adding anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure to obtain light yellow syrup. Then, it was separated by silica gel column chromatography to obtain a colorless transparent syrup, 2c, with a yield of 56%. IR (KBr, cm -1 )υ: 1693, 1601, 1505, 1308, 1245, 1161, 1094, 832, 737, 698; 1 H NMR (CDCl 3 , 300MHz) δ: 9.90(s, 1H, CHO), 8.04-7.92, 7.67-7.29, (m, 20H, ArH), 7.73(d, J=8.6Hz, 2H, ArH...

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Abstract

An application of helicidum analog in preparing medicines for preventing and treating depression is disclosed. Its chemical structure is also disclosed.

Description

technical field [0001] The invention relates to tofu glucoside analogs and their application in antidepressants. technical background [0002] With the intensification of various emergency factors, depression has become a common disease in modern society, with a high incidence rate, and its incidence rate is rising rapidly. It is estimated that by 2020, depression will be the second major disease (after ischemic heart disease) that endangers human health and shortens life span. Most of the antidepressants that have been on the market have defects such as narrow antidepressant spectrum, large side effects, high drug price and easy relapse. Therefore, the research and development of antidepressants at home and abroad pay more and more attention to traditional medicines, including Chinese herbal medicines and ethnic medicines. [0003] Tofu fruit glycoside (Helicid) comes from the traditional medicine of the Jingpo people in Yunnan, my country. It belongs to the active ingred...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/203C07H15/26C07D239/60A61K31/7034A61K31/7052A61K31/505A61P25/24
Inventor 闻环王子厚阙灵彭文烈宋化灿曹日晖童九翠谢海棠江云艳孙瑞元李云峰杨红菊赵楠罗质朴戴晓畅胡利昆张利生王艳华
Owner KUNMING BAKER NORTON PHARMA
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