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Preparation method and usage for nitrogen-containing chalcone derivatives

A technology of chalcone derivatives and compounds, which is applied in the field of synthesis of organic compounds, can solve problems such as in-depth research on the mechanism of anti-tumor effects, and achieve the effects of easy preparation, mild reaction conditions, and simple operation

Inactive Publication Date: 2007-09-26
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The author only conducted a preliminary discussion on the activity and structure-activity relationship of these compounds, but did not conduct further in-depth research on the mechanism of their anti-tumor effects

Method used

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  • Preparation method and usage for nitrogen-containing chalcone derivatives
  • Preparation method and usage for nitrogen-containing chalcone derivatives
  • Preparation method and usage for nitrogen-containing chalcone derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1, 2-hydroxy-4,6-dimethoxy-acetophenone (compound III): prepared according to the literature method (I.Kazuhiko et al, J Nat.Prod., 1988, 51, 906-914) have to.

[0027] M.p.77~78℃.

[0028] 1 H-NMR (δ, CDCl 3 ): 14.06(s, 1H), 6.05(d, 1H, J=2.4Hz), 5.92(d, 1H, J=2.4Hz), 3.90(s, 3H), 3.62(s, 3H), 2.63(s , 3H).

Embodiment 2

[0029] Example 2, 2'-hydroxyl-4', 6'-dimethoxy-2-chloro-chalcone (compound IVa): refer to literature method (X.Y.Bu et al, Synthesis, 1997, 11, 1246-1248 )be made of.

[0030] M.p.123~124℃.

[0031] 1 H-NMR (δ, CDCl 3 ): 14.20(s, 1H,), 8.14(d, 1H, J=15.6Hz), 7.87(d, 1H, J=15.6Hz), 7.68-7.70(m, 1H), 7.42-7.44(m, 1H ), 7.26-7.31 (m, 2H), 6.11 (s, 1H), 5.96 (s, 1H), 3.90 (s, 3H), 3.84 (s, 3H).

Embodiment 3

[0032] Example 3, 3'-allyloxy-4', 6'-dimethoxy-2-chloro-chalcone (compound Va):

[0033] 3.2g (10.0mmol) of compound IV, 2.0g (15.0mmol) of anhydrous potassium carbonate and 30mL of anhydrous acetone were put into the reaction flask, and 10.4mL (12.0mmol) of allyl bromide was added dropwise with stirring. After the addition, the temperature was raised to reflux for 4 hours. After cooling the reaction liquid, a small amount of solid precipitated out, which was suction filtered, and the filtrate was recovered under reduced pressure to obtain 3.4 g of light yellow liquid with a yield of 95%.

[0034] 1 H-NMR (δ, CDCl 3): 7.79(d, 1H, J=16.0Hz), 7.66(m, 1H), 7.39(m, 1H), 7.28(m, 2H), 6.93(d, 1H, J=16.0Hz), 6.16(d , 1H, J=2.0Hz), 6.14(d, 1H, J=2.0Hz), 5.95(m, 1H), 5.33(dd, 1H, J 1 =15.8Hz,J 2 =1.2Hz), 5.50(m, 2H), 3.84(s, 3H), 3.78(s, 3H).

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Abstract

The invention discloses a making method of 2'-hydroxy-3'-alkylamino propyl-4', 6'-disubstituted chalcone derivant, which comprises the following steps: adopting 2'-hydroxy chalcone as leading material; proceeding allyl etherifying reaction on the mother core of 2'-hydroxy chalcone; proceeding Claisen rearrangement; epoxidising; additioning; obtaining the product; fitting for industrial manufacturing; improving the receiving rate obviously.

Description

technical field [0001] The invention belongs to the synthesis of organic compounds, and relates to the preparation method of nitrogen-containing chalcone derivatives, in particular to the preparation of 2'-hydroxy-3'-alkylaminopropyl-4',6'-disubstituted chalcone derivatives Method, and its application in the preparation of antitumor drugs. Background technique [0002] Chalcone derivatives have antitumor effects. In 2000, X.Yi et al reported a series of 2'-aminochalcone derivatives, most of which showed strong cytotoxic activity, especially 2'-amino-4', 5'-methylenedi Oxy-3-methoxychalcone, IC for various tumor cells (KB, HOS, HCT-8, A-549, etc.) 50 are less than 1 μM. Moreover, it also exhibited strong inhibitory activity against multidrug-resistant tumor cells KB-VIN and 1A9. The nitrogen-containing chalcone derivatives provided in this article have a relatively common structure, and the aromatic ring is substituted with methoxy, hydroxyl, amino, etc. The author only ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/112C07C225/16A61K31/137A61K31/5375A61K31/495A61K31/40A61P35/00
Inventor 刘滔徐仲淼胡永洲何俏军杨波杨晓春
Owner ZHEJIANG UNIV
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