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Synthesis of oroxylin

A synthesis method, the technology of melaleuca, applied in the directions of drug combination, digestive system, antipyretics, etc., can solve the problem of high cost, and achieve the effects of simple steps, high product purity, and mild conditions

Active Publication Date: 2009-08-19
南京芩领医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material wogonin used in this method needs to be synthesized by multi-step reactions, and the cost is high. It is only suitable for research and is not suitable for the large-scale synthesis of kelp.

Method used

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  • Synthesis of oroxylin
  • Synthesis of oroxylin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of 7-benzyl-5,6-dihydroxyflavone

[0031] Add 16g of baicalein and 1600mL of acetone in a 2000ml reaction flask equipped with a mechanical stirrer, a thermometer, and a nitrogen inlet tube, and feed N 2 Replace the air, keep the nitrogen flowing, heat to 32°C to completely dissolve the baicalein, add K 2 CO 3 59g, 10mL of benzyl bromide, reacted for 48h, cooled, concentrated to dryness under reduced pressure, added 200ml of water, stirred, filtered, and dried to obtain 15.5g of yellow solid, yield 92%, Mp: 195°C-196°C. 10% FeCl 3 Ethanol solution is dark green

[0032] 1 H-NMR (DMSO-d 6 , 300Hz): δ 5.30 (2H, s, CH 2 Ph), 7.01 (1H, s, 3H), 7.12 (1H, S, 8H) 7.33-7.65 (10H, m, ArH), 8.08-8.10 (2H, d, ArH), 8.83 (1H, s, 6- OH), 12.55 (1H, s, 5-OH) MS (EI, m / z) 360, 269, 241, 139, 91

Embodiment 2

[0034] Preparation of 7-benzyloxy-5,6-dihydroxyflavone

[0035] Add baicalein 16g (59mmol) and ethanol 1500mL in the 2000ml reaction bottle that mechanical stirrer, thermometer are housed, nitrogen inlet pipe, pass into N 2 Replace the air, keep the nitrogen flowing, heat to 40°C to completely dissolve the baicalein, add Na 2 CO 3 55g, 15mL of benzyl bromide, reacted for 24h, cooled, concentrated to dryness under reduced pressure, added 200ml of water, stirred, filtered, and dried to obtain 14.0g of yellow solid, yield 77%, Mp: 195°C-196°C. 10% FeCl 3 The ethanol solution is dark green.

Embodiment 3

[0037] Preparation of 7-benzyloxy-5,6-dihydroxyflavone

[0038] Add baicalein 16g (59mmol) in the 2000ml reaction bottle that mechanical stirrer, thermometer are housed, nitrogen inlet tube, acetone 1500mL, pass into N 2 Replace the air, heat to 40°C to dissolve the baicalein completely, add KHCO 3 59g, 15mL of benzyl bromide, reacted for 24h, cooled, concentrated to dryness under reduced pressure, added 200ml of water, stirred, filtered, and dried to obtain 13.0g of yellow solid, yield 82%, Mp: 195°C-196°C. 10% FeCl 3 The ethanol solution is dark green.

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Abstract

The invention relates to the chemical synthesis field, in particular to a synthetic method of traditional Chinese herbal skullcap momoner oroxylin. The method is characterized by comprising the following steps: 5,6,7-trihydroxyflavone, benzyl bromide and benzyl chloride are subject to nucleophilic substitution reaction in the presence of an acid coating agent to generate 7-benzyl-5,6-dihydroxyflavone, the generated 7-benzyl-5,6-dihydroxyflavone reacts with dimethyl sulfate in the presence of the acid coating agent to generate 7-benzyl-6-methoxyl-5-hydroxylflavone; and the 7-benzyl-6-methoxyl-5-hydroxylflavone is subject to debenzylation in the presence of palladium-carbon under the reducing action of catalytic hydrogenation to obtain the oroxylin. The method has the advantages of simple steps, mild conditions, more than 65% of total reaction yield and high synthetic product purity of more than 99.0%.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular, the invention relates to the synthesis of scutellaria baicalensis monomer melaleucain. Background technique [0002] Melaleucain is a flavonoid compound contained in the root of Scutellaria baicalensis Georgi, which has a structure of formula (I). [0003] [0004] Formula (I) [0005] Studies have shown that celesteol has a variety of pharmacological effects, including improving memory deficits mediated by scotronine and cerebral blood perfusion, mediating apoptosis of the liver cancer cell line HepG2, anti-inflammatory, liver protection, and sleep suppression. [0006] Due to the wide range of pharmacological activities of celesteol, and the extraction process from plants is cumbersome, the purity is low, and the cost is high, people have explored its total synthesis method. [0007] There are mainly the following five methods for the full synthesis of paper paper [0008]...

Claims

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Application Information

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IPC IPC(8): C07D311/60A61P25/28A61P35/00A61P29/00A61P1/16A61P43/00
Inventor 李志裕符伟杨博郭青龙尤启冬
Owner 南京芩领医药科技有限公司
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