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Biochemical total synthetic method for protosappanin A and derivatives thereof

A synthesis method and hematoxylin technology, applied in the direction of organic chemistry, etc., can solve the problems such as the specific mechanism needs to be further studied, the scavenging of free radicals is weak, etc., and the effect of good industrial production prospects, easy operation and high yield can be achieved.

Inactive Publication Date: 2014-09-03
HEILONGJIANG UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0011] In 2005, T.Mai research group (T.Mai, A.Suresh, Z.Yasuhiro, L.T.Quan, K.Shigetos. Xanthine Oxidase Inhibitors from the Heartwood of Vietnamese Caesalpinia sappan.Chem.Pharm.Bull., 2005, (8 ): 984-988.) found that prohematoxylin A has xanthine oxidase inhibitory activity, and further studies have shown that it has the same mechanism of action as xanthine oxidase inhibitor Allopurinol, which is widely used clinically. Both are competitive inhibitors. The specific mechanism of its action remains to be further studied, which may bring good news to the development of drugs for the treatment of hyperuricemia
Although the 95% ethanol extract of sumac can strongly inhibit the formation of lipid peroxidation products, and the concentration and activity show a good linear relationship, but its ability to scavenge other free radicals is weak

Method used

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  • Biochemical total synthetic method for protosappanin A and derivatives thereof
  • Biochemical total synthetic method for protosappanin A and derivatives thereof
  • Biochemical total synthetic method for protosappanin A and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0059] Example 13,10,11-trimethoxy-6H-dibenzo[b,d]oxetane-7(8H)-one

[0060]

[0061] 3,9,10-Trimethoxydibenzo[d,f]oxepan-3-one (400mg, 1.33mmol), zinc iodide (85mg, 0.27mmol), dichloromethane (5mL) were added Add cyanotrimethylsilane (450 mmL, 3.33 mmol) into the reaction flask, and stop the reaction at room temperature for 12 hours. Add 6% NaHCO to the reaction solution 3 The solution (10 mL) was reacted at room temperature for 30 minutes, the aqueous phase was separated, the organic phase was dried over anhydrous sodium sulfate for 2 hours, filtered, and dichloromethane was spun off to obtain a seven-membered cyclocyanosilyl ether compound (430 mg, 1.30 mmol). The obtained seven-membered ring cyanide was dissolved in 30 mL of anhydrous ether, lithium aluminum hydride (126 mg, 3.33 mmol) was added, and the reaction was carried out at room temperature for 20 hours under airtight conditions. After the reaction was completed, the reaction was quenched by adding a small amo...

Embodiment 23

[0069] Example 23-Methoxy-6H-dibenzo[b,d]oxetane-7(8H)-one

[0070]

[0071] 3-Methoxydibenzo[d,f]oxepan-3-one (400mg, 1.66mmol), zinc iodide (106mg, 0.33mmol), dichloromethane (5mL) were added to the reaction flask , add cyanotrimethylsilane (560mmL, 4.16mmol), and stop the reaction at room temperature for 12 hours. Add 6% NaHCO to the reaction solution 3 The solution (10 mL) was stirred at room temperature for 30 minutes, the aqueous phase was separated, the organic phase was dried over anhydrous sodium sulfate for 2 hours, filtered, and dichloromethane was spun off to obtain a seven-membered cyclocyanosilyl ether compound (436 mg, 1.60 mmol). The obtained seven-membered ring cyanide was dissolved in 30 mL of anhydrous ether, lithium aluminum hydride (158 mg, 4.16 mmol) was added, and the mixture was reacted at room temperature for 20 hours under airtight conditions. After the reaction was completed, the reaction was quenched by adding a small amount of water in an ice ...

Embodiment 310

[0079] Example 310,11-trimethoxy-6H-dibenzo[b,d]oxetane-7(8H)-one

[0080]

[0081] 9,10-Dimethoxydibenzo[d,f]oxepan-3-one (400mg, 1.48mmol), zinc iodide (95mg, 0.29mmol), dichloromethane (5mL) were added to In the reaction bottle, cyanotrimethylsilane (500 mmL, 3.70 mmol) was added, and the reaction at room temperature was stopped for 12 hours. Add 6% NaHCO to the reaction solution 3 The solution (10 mL) was stirred at room temperature for 30 minutes, the aqueous phase was separated, the organic phase was dried over anhydrous sodium sulfate for 2 hours, filtered, and dichloromethane was spun off to obtain a seven-membered cyclocyanosilyl ether compound (435 mg, 1.44 mmol). The obtained seven-membered ring cyanide was dissolved in 30 mL of anhydrous ether, lithium aluminum hydride (158 mg, 4.16 mmol) was added, and the mixture was reacted at room temperature for 20 hours under airtight conditions. After the reaction was completed, a small amount of water was added to quen...

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Abstract

The invention discloses a biochemical total synthetic method for protosappanin A and derivatives thereof. The synthetic method for protosappanin A and derivatives thereof comprises the main steps: taking a dibenzo[d,f]oxepane-3-one compound as a raw material, performing cyan addition on carbonyl, performing reduction, Tiffeneau-Demjanov rearrangement, deprotection and other reactions, so as to synthesize the protosappanin A derivatives with the total yield of 85% or more. Chemical total synthesis of protosappanin A compounds is developed for the first time. The synthetic method is simple to operate, reduced in synthetic difficulty because routine chemical reaction methods are employed, mild in reaction conditions, friendly to environment, simple in post-treatment and high in yield, and has good industrialization production prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a chemical total synthesis method of prohematoxylin A and its derivatives. Background technique [0002] Sappan (Caesalpinina sappan L) is a leguminous plant, also known as sappan, sappan, red wood, palm wood, and red wood. It was first recorded in "Tang Materia Medica". Sumac has the effects of relaxing tendons and collaterals, promoting blood circulation and dispelling stagnation, calming, eliminating phlegm, and relieving pain. In recent years, scholars at home and abroad have shown that: in addition to the traditional efficacy of sumac, it also has new pharmacological activities, such as anti-tumor, anti-inflammatory, anti-oxidation, anti-complement and immunosuppressive effects. In addition, as a natural pigment, sumac is widely used in industries such as daily chemical, food, leather and knitted fabric dyeing, and it is also used as a staining agent for cell t...

Claims

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Application Information

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IPC IPC(8): C07D313/20
CPCC07D313/20
Inventor 初文毅袁小彬孙志忠兰昊刘佳奇王加林周旋
Owner HEILONGJIANG UNIV
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