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Polysubstituted flavanone derivative and its prepn and application

A derivative, the technology of amine methylene flavanone, applied in the field of synthesis of organic compounds, can solve problems such as the mechanism of anti-tumor effect that has not been studied in depth

Inactive Publication Date: 2007-11-07
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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  • Polysubstituted flavanone derivative and its prepn and application
  • Polysubstituted flavanone derivative and its prepn and application
  • Polysubstituted flavanone derivative and its prepn and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1, 2'-hydroxyl-3'-(morpholin-1-yl-methyl)-4',6'-dimethoxy-2-chloro-chalcone (IVa):

[0023] 1.59g (4.99mmol) of compound III, 1.24g (15.30mmol) of formaldehyde aqueous solution, 1.00g (11.49mmol) of morpholine, 13ml of methanol and hydrochloric acid were added dropwise into the reaction flask, and refluxed for 2h. Cool, recover the solvent under reduced pressure, dilute with water, basify, extract with dichloromethane, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, recover the solvent under reduced pressure, and separate by column chromatography to obtain 1.30 g of a yellow solid with a yield of 61%. m.p.162-164°C.

[0024] 1 HNMR (CDCl 3 ): δ8.04(d, 1H, J=15.6Hz), 7.70-7.68(m, 1H), 7.57(d, 1H, J=15.6Hz), 7.43-7.41(m, 1H), 7.30-7.28( m, 2H), 6.02(s, 1H), 3.91(s, 3H), 3.89(s, 3H), 3.71(t, 4H, J=4.4Hz), 3.67(s, 2H), 2.56(t, 4H , J=4.4Hz).

Embodiment 2

[0025] Example 2, 2'-hydroxyl-3'-(piperidin-1-yl-methyl)-4',6'-dimethoxy-2-chloro-chalcone (IVb):

[0026] Refer to Example 1 for the operation process, except that piperidine is used instead of morpholine to obtain yellow crystals with a yield of 50%, m.p.159-162°C.

[0027] 1 HNMR (CDCl 3 ): δ7.94(d, 1H, J=16.0Hz), 7.69-7.66(m, 1H), 7.38-7.36(m, 1H), 7.26-7.24(m, 2H), 7.22(d, 1H, J =16.0Hz), 5.99(s, 1H), 3.82(s, 3H), 3.81(s, 3H), 3.66(s, 2H), 2.50-2.40(m, 4H), 1.59-1.55(m, 4H) , 1.42-1.40 (m, 2H).

Embodiment 3

[0028] Example 3, 2'-hydroxyl-3'-(tetrahydropyrrol-1-yl-methyl)-4',6'-dimethoxy-2-chloro-chalcone (IVc):

[0029] Refer to Example 1 for the operation process, except that tetrahydropyrrole is used instead of morpholine to obtain yellow crystals with a yield of 50% and m.p.125-127°C.

[0030] 1 HNMR (CDCl 3 ): δ8.05(d, 1H, J=15.6Hz), 7.70-7.68(m, 1H), 7.54(d, 1H, J=15.6Hz), 7.43-7.40(m, 1H), 7.30-7.28( m, 2H), 6.02 (s, 1H), 3.94 (s, 2H), 3.93 (s, 3H), 3.91 (s, 3H), 2.86 (brs, 4H), 1.89 (brs, 4H).

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Abstract

The present invention provides one kind of nitrogen atom-containing polysubstituted flavone derivatives, 2-substituent phenyl-5, 7-dioxy-8-amino methylene flavone derivatives, which are synthesized through introducing different amino methylene structures into the 8-position of flavone kernel. Pharmacological activity experiments shows that the 2-substituent phenyl-5, 7-dioxy-8-amino methylene flavone derivatives have certain antitumor activity, high selectivity and cell period inhibiting effect and may be applied in antitumor medicine. The present invention has the general structural expression of the 2-substituent phenyl-5, 7-dioxy-8-amino methylene flavone derivatives shown.

Description

technical field [0001] The invention belongs to the synthesis of organic compounds, relates to multi-substituted flavanone derivatives and preparation methods, mainly 2-substituted phenyl-5,7-dioxygen-containing functional group-8-amine methylene flavanone derivatives and Its preparation method and its application in the preparation of antitumor drugs. Background technique [0002] Flavanone derivatives have antitumor effects. In 2001, C. Pouget et al. reported that a series of flavanone derivatives containing methoxy and hydroxyl groups in the A ring had antitumor effects, among which 7-methoxyflavanone, 5-methoxyflavanone and 5 , 7-dimethoxyflavanone has antiproliferative activity on human breast cancer cell line MCF-7, IC 50 Values ​​were 35.7-36 μM. The author only conducted a preliminary study on the structure-activity relationship of these compounds, but did not study the mechanism of their anti-tumor effects in depth. Contents of the invention [0003] The objec...

Claims

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Application Information

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IPC IPC(8): C07D311/32A61K31/353A61K31/453A61K31/5377A61K31/4025A61K31/496A61P35/00
Inventor 胡永洲刘滔何俏军杨波罗沛华
Owner ZHEJIANG UNIV
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