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Preparation of a quercetin combined hydrogen sulfide donor and its application in the treatment of diabetes and wound healing

A technology of quercetin and thione, applied in skin diseases, organic chemistry, metabolic diseases, etc., can solve the problems of no clinical significance, poor cell permeability, easy decomposition, etc., and achieves environmental protection of the solvent, simple operation steps, and raw materials. easy-to-get effect

Active Publication Date: 2022-04-15
HUBEI UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its shortcoming is that: due to the relatively large molecular structure of the drug after splicing, it often has a large discrepancy with the envisaged target
After the structure of the drug changes, the absorption, transport, and metabolism of the drug in the body also change, which will lead to complex pharmacodynamics.
For example, the assembled molecules generally have a relatively large molecular weight, so their cell permeability is poor; and the molecular structure is large, relatively unstable in nature and easy to decompose, which often leads to no actual medicinal value; in addition Some molecules are too stable in the body, are not sensitive to hydrolytic enzymes, and cannot release the target drug quickly and quantitatively, so there is no clinical significance

Method used

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  • Preparation of a quercetin combined hydrogen sulfide donor and its application in the treatment of diabetes and wound healing
  • Preparation of a quercetin combined hydrogen sulfide donor and its application in the treatment of diabetes and wound healing
  • Preparation of a quercetin combined hydrogen sulfide donor and its application in the treatment of diabetes and wound healing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1, 3 ', 4 ', the synthesis of 7-O-tribenzyl quercetin

[0045]

[0046] Dissolve 8 mmol rutin in 40 ml DMF, then add anhydrous K 2 CO 3 28mmol, stirred under nitrogen for 0.5h, added dropwise 32mmol of benzyl bromide, reacted at 60°C for 3h, then adjusted the pH to 5 with glacial acetic acid (referring to glacial acetic acid aqueous solution with a concentration of 10% by volume), filtered, and dissolved the solid in 120ml Add 18ml of concentrated hydrochloric acid to ethanol, reflux for 2h, cool to room temperature, filter to obtain a yellow solid, filter and dry to obtain 3.5g of yellow crude product, the yield is 71.7%. 1 H NMR(400MHz,dmso)δ12.40(s,1H),9.67(s,1H),7.88(s,1H),7.81(s,1H),7.49-7.33(m,15H),7.24(s, 1H),6.83(s,1H),6.42(s,1H),5.22(s,6H). 13 C NMR(101MHz,dmso)δ176.53,164.44,160.87,156.43,150.44,148.21,146.75,137.43,137.24,137.09,136.57,128.89,128.32,128.08,124.00,122.42,114.20,104.63,98.44,93.48,70.94,70.45 ,70.35.m.p.190~192℃.

Embodiment 2

[0047] Embodiment two, 3', 4', the synthesis of 7-O-tribenzylquercetin-3-O-ethyl acetate

[0048]

[0049] Take 4mmol (2.3g) of 3',4',7-O-tribenzylquercetin prepared in Example 1 and dissolve in 60ml DMF, add anhydrous K 2 CO 3 5mmol, stirred at room temperature for 30min, then slowly added dropwise 15ml DMF solution containing 4.4mmol ethyl bromoacetate, reacted at room temperature for 2h, adjusted the pH to 6 with glacial acetic acid, extracted 3 times with ethyl acetate, collected the ethyl acetate layer, and used Wash with saturated brine, concentrate by rotary evaporation, and pass through the column (the eluent is acetone / petroleum ether with a volume ratio of 1:4) to obtain 0.5 g of light yellow filamentous solid with a yield of 21.7%. 1 H NMR (400MHz, dmso) δ12.47-12.31 (m, 1H), 7.88 (d, J=2.1Hz, 1H), 7.84-7.72 (m, 1H), 7.69-6.85 (m, 14H), 6.84- 6.59(m,1H),6.57-5.96(m,2H),5.54-5.21(m,4H),5.21-4.93(m,2H),4.79(d,J=16.9Hz,2H),4.21-3.97( m,2H),1.35-0.99(m,3H). 13 C...

Embodiment 3

[0050] Embodiment three, 3', 4', the synthesis of 7-O-tribenzylquercetin-3-O-acetic acid

[0051]

[0052] Take 4 mmol of 3',4',7-O-tribenzylquercetin-3-O-ethyl acetate prepared in Example 2 and 100 ml of distilled aqueous solution containing 200 mmol of NaOH, reflux for 3 hours, cool to room temperature, and adjust the pH to 2-3, extracted with ethyl acetate, washed the organic layer with water, concentrated by rotary evaporation, and dried to obtain 2.36 g of dark yellow powder solid with a yield of 90%. 13 C NMR(101MHz,dmso)δ178.11,170.36,164.63,161.30,156.49,154.91,151.25,148.09,137.48,137.18,136.97,136.48,128.95,128.27,127.99,122.81,114.85,113.89,105.60,98.86,93.69,70.66 ,70.49,70.32,68.33. 1 H NMR(400MHz,dmso)δ13.01(s,1H),12.45(s,1H),7.98(s,1H),7.75(s,1H),7.48-7.33(m,15H),7.18(s, 1H),6.80(s,1H),6.42(s,1H),5.21(s,6H),4.74(s,2H).m.p.164~165℃.

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Abstract

The invention belongs to the technical field of preparing medicines for treating diabetes and wound healing thereof, in particular to quercetin-3-O-acetic acid-(4-(3H-1,2-dithiolene-3-thione) )-phenyl ester and its application in the preparation of medicines for treating diabetes and its wound healing. The present invention uses rutin as a raw material, undergoes two substitution hydrolysis reactions, and then reduces quercetin-3-O-acetic acid to form quercetin-3-O-acetic acid, which is combined with hydrogen sulfide donor 5-(4-hydroxyphenyl)-3H-1,2 ‑Dithiolene‑3‑thione successfully prepared a compound entity capable of simultaneously treating diabetes and promoting wound healing through condensation reaction. In the HUVECs cell experiment, the cell proliferation experiment verified that it can promote the growth of HUVECs cells, and the scratch experiment and in vitro tubule formation experiment further verified that it can promote wound healing in diabetic patients. In the HepG 2 cytotoxicity experiment, it was verified that the drug had no damage to liver cells, and it was verified that the compound had a similar hypoglycemic effect to the marketed drug metformin through the treatment of insulin resistance models.

Description

technical field [0001] The invention belongs to the technical field of preparation of medicines for treating diabetes and wound healing thereof, in particular to a quercetin derivative and 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-sulfur The design and synthesis of compound B after ketone splicing and its application in the preparation of medicines for the treatment of diabetes and its wound healing, especially related to a kind of quercetin-3-O-acetic acid-(4-(3H-1,2-disulfide Heterocyclopentene-3-thione))-phenyl ester and its application in the preparation of medicines for treating diabetes and its wound healing. Background technique [0002] Quercetin, also known as quercetin. It has a higher content in plants such as rutin (rutin), quercetin, and hyperoside. It is a natural medicine extracted from plants, which has good expectorant and cough-relieving effects, and has a certain anti-asthma effect. It has the effects of lowering blood pressure, enhancing capillary resistan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/12A61P3/10A61P17/02A61P5/50
CPCC07D409/12A61P3/10A61P17/02A61P5/50
Inventor 刘明星刘建程百川詹一丰
Owner HUBEI UNIV OF TECH
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