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Preparation method and usage for nitrogen-containing chalcone derivatives

A technology for chalcone derivatives and compounds, which is applied in the field of organic compound synthesis, can solve problems such as in-depth research on the mechanism of anti-tumor effect, and achieve the effects of easy preparation, high yield in each step, and wide sources.

Inactive Publication Date: 2011-07-20
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 a 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 present 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; and thus, obtaining 2'-hydroxy-3'-alkylamino propyl-4',5',6'-trisubstituted chalcone derivant; The pharmacology experiment appears and proves that the chalcone derivant has the inhibitory effect on proliferation in vitro and can be used for preparing anti-tumors medicines. The making method of 2'-hydroxy-3'-alkylamino propyl-4', 6'-disubstituted chalcone derivant provided by the present invention has the advantages that the materials have extensive sources; the derivant is easy to prepare; the reaction condition is mild; the yield coefficient for each step is high; the production cost is lower and is fit for industrial manufacturing. The general structure formula is...

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 Patents(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