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E-3-(phenyl derivative-methenyl)-pyrano dihydroflavone derivative as well as preparation and application

A technology of pyranodihydroflavones and dihydroflavones, which is used in the fields of chemistry, cosmetics and medicine, can solve the problems of inability to carry out aldol condensation, restriction of ester bond protection, many side reactions, etc., and it is easy to achieve the fat-water distribution coefficient. Adjusted, expanded conjugation, easy to purify effect

Active Publication Date: 2017-05-31
YICHUN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] When 7-OH is protected by benzyl, methoxy, etc., it is easy to open the ring and generate chalcone, which has good inertness and cannot undergo aldol condensation.
Therefore, for flavanones containing 7-OH, there are serious difficulties in condensing benzaldehyde and its derivatives at its 3-position.
[0007] Protect 7-OH with an acid anhydride to form an ester bond. Due to the aldol condensation, acid-base catalysis is required, and the ester bond is easily hydrolyzed, resulting in more side reactions and low yield. Therefore, the protection of the ester bond is also significantly limited.

Method used

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  • E-3-(phenyl derivative-methenyl)-pyrano dihydroflavone derivative as well as preparation and application
  • E-3-(phenyl derivative-methenyl)-pyrano dihydroflavone derivative as well as preparation and application
  • E-3-(phenyl derivative-methenyl)-pyrano dihydroflavone derivative as well as preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: E-3-(3,4,5-triOCH 3 Preparation of benzylidene)-8,8-dimethylpyranohesperetin: Take 0.404g of 8,8-dimethylpyranohesperetin, 3,4,5-triOCH 3 0.223 g of benzaldehyde, 5.0 mL of tetrahydrofuran, 140 μL of pyrrole, 130 μL of glacial acetic acid, and react in a closed manner at 70°C for 24 hours. The reaction solution was recovered to 1 / 2 of its volume, and the sample was mixed with silica gel. Using petroleum ether-ethyl acetate=3 / 1 as the eluent, the orange-yellow-brown color band was collected, and the solvent was recovered to obtain 412 mg of orange-yellow solid (Cpd1). 1 H NMR (400MHz, CDCl 3)δ12.92(s,1H:5-OH),7.97(s,1H:1”-H),7.10(d,J=2.1Hz,1H:2’-H),6.90(dd,J=8.3 ,1.9Hz,1H:6'-H),6.78(d,J=8.3Hz,1H:5'-H),6.57(d,J=10.1Hz,1H:10-H),6.48(d,3H :3”-H+7”-H+H-2),5.83(s,1H:6-H),5.62(s,1H:3’-OH),5.44(d,J=10.1Hz,1H: 9-H),3.86(s,6H:4'-OCH 3 +5”-OCH 3 ),3.65(s,6H:6”-OCH 3 +4”-OCH 3 ), 1.39(d, J=10.2Hz, 6H:(8-CH 3 ) 2 ; 13 C NMR (101MHz, CDCl 3 )δ185.01(C-4), 162.3...

Embodiment 2

[0031] Example 2: E-3-(3,4-diOCH 3 The preparation of benzylidene)-8,8-dimethylpyranohesperetin: take, 8-dimethylpyranohesperetin 0.368g, 3,4-diOCH 3 0.180 g of benzaldehyde, 5.0 mL of tetrahydrofuran, 120 μL of pyrrole, 100 μL of glacial acetic acid, and react at 70°C for 24 hours in a sealed manner. Recover the reaction solution to 1 / 2 of its volume, mix the sample with silica gel, use petroleum ether-ethyl acetate=3.5 / 1 as the eluent, collect the orange-yellow-brown color band, and recover the solvent to obtain 382 mg of orange-yellow (Cpd2). 1 H NMR (400MHz, CDCl 3 )δ12.97(s,1H:5-OH),7.99(s,1H:1”-H),7.11(d,J=2.1Hz,1H:2’-H),6.90(dd,J=8.3 ,1.8Hz,2H:H-6'+7”-H),6.84(d,J=8.4Hz,1H:5’-H),6.77(d,J=8.0Hz,2H:6”-H+ 3”-H), 6.57(d,J=10.0Hz,1H:10-H),6.49(s,1H:H-2),5.83(s,1H:H-6),5.63(s,1H: 3'-OH), 5.43(d,J=10.0Hz,1H:9-H),3.87(d,6H:4'-OCH 3 +5”-OCH 3 ),3.67(s,3H:4”-OCH 3 ),1.39(d,6H:(8-CH 3 ) 2 ; 13 C NMR (101MHz, CDCl 3 )δ185.25 (C-4), 162.16 (C-7), 159.67 (C-5), 159.18 (C-10...

Embodiment 3

[0033] Example 3: E-3-(3,4,5-triOCH 3 Preparation of benzylidene)-8,8-dimethyldihydropyranohesperetin:

[0034] Weigh 0.154 g of 8,8-dimethyldihydropyranohesperetin, three OCH 3 0.084g of benzaldehyde, 4.0mL of tetrahydrofuran, 40ul of tetrahydropyrrole, 30μL of glacial acetic acid, stirred and reacted at 75°C for 24h, recovered the reaction liquid to 1 / 2 of the volume, mixed the sample with silica gel, washed with petroleum ether-ethyl acetate=3 / 1 The agent was removed, the orange-yellow-brown ribbon was collected, and the solvent was recovered to obtain 161 mg of a yellow solid (Cpd3).

[0035] 1 H NMR (400MHz, CDCl 3 )δ13.00(s,1H:5-OH),7.96(s,1H:1”-H),7.10(d,J=1.8Hz,1H:2’-H),6.90(dd,J=8.3 ,1.8Hz,1H:6'-H),6.78(d,J=8.3Hz,1H:5'-H),6.5(s,2H:3”-H+7”-H),6.46(s, H:2-H),5.82(s,1H:6-H),5.60(s,1H:3'-OH),3.85(6H:4'-OCH 3 +5”-OCH 3 ),3.65(s,6H:6”-OCH 3 +4”-OCH 3 ),2.14-2.69(M,2H:10-CH 2 ),1.56-1.79(M,2H:9-CH 2 ),1.29-1.31(s,6Hz,(8-CH 3 ) 2 ); 13 C NMR (101MHz, CDCl 3 ) δ...

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Abstract

The invention discloses an E-3-(phenyl derivative-methenyl)-pyrano dihydroflavone derivative as well as preparation and application. The structural general formula of the E-3-(phenyl derivative-methenyl)-pyrano dihydroflavone derivative is shown as (I) in the specification, wherein R1 can be -H, -CH3, -CH2CH3, -CH2CH2CH3, -CH=C(CH3)2 and -CH=C(CH3)CH2CH2CH=C(CH3)2; R2 can be -H and -CH3; R3 can be -H and -OH; R4 can be a single radical or multiple radicals in -H, -OH, -OCH3, -N(CH3)2, -F and -Cl; R5 can be a single radical or multiple radicals in -OH, -OCH3, -N(CH3)2-F, -Cl and -COOH; and X can be -CH or -CH2. A pyrano dihydroflavone compound reacts with a benzaldehyde derivative in one step through organic amine catalysis, so that the derivative is obtained. The technology is simple, and industrial production is facilitated. The derivative has referable anti-inflammatory and antioxidation effects, and has potential clinical application prospects.

Description

[0001] Technical field: [0002] The invention belongs to the fields of chemistry, cosmetics and medicine, and relates to an E-3-(phenyl derivative-methine)-pyranodihydroflavone derivative and its preparation and application. Background technique [0003] There are many kinds of flavonoids in nature, the content is abundant, the extraction and preparation process is simple, and the price is low. Due to the secondary metabolites of natural flavonoids plant enzymes, they mostly contain phenolic hydroxyl groups. Due to the uneven distribution of phenolic hydroxyl groups, which occupy two benzene rings, no o-diphenol OH is formed, and the antioxidant effect is weak. Representative compounds such as hesperidin, naringin, neohesperidin, and diosmin , Rhodorin, apigenin, hesperetin, naringenin, methyl hesperidin. Even if it contains ortho-diphenolic hydroxyl groups, because the two benzene rings have better coplanarity, the molecules are easy to arrange in layers, forming crystals,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A61K31/352A61P31/00A61P31/12A61P35/00A61P9/00A61P29/00A61P39/06A61K8/49A61Q17/00A23L33/10
CPCA23V2002/00A61K8/498A61Q17/00C07D493/04A23V2200/308A23V2200/326A23V2200/30
Inventor 郭孟萍申秀丽闻永举
Owner YICHUN UNIVERSITY