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Poly-substituted flavan zothia dizoline kind compound and preparation process and use thereof

A technology of thiadiazolines and compounds, applied in the field of synthesis of organic compounds

Inactive Publication Date: 2006-06-28
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In addition, many compounds containing thiadiazole fragments have antitumor toxicity

Method used

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  • Poly-substituted flavan zothia dizoline kind compound and preparation process and use thereof
  • Poly-substituted flavan zothia dizoline kind compound and preparation process and use thereof
  • Poly-substituted flavan zothia dizoline kind compound and preparation process and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: Preparation of flavanone-4-(4-nitrophenyl) hydrazone (compound IVa)

[0025] Add 0.448g (2mmol) of flavanone, 0.306g (2mmol) of 4-nitrophenylhydrazine, 20mL of ethanol and 0.02mL of acetic acid into the reaction flask, and reflux for 6hr. After the solid dissolves, a yellow solid precipitates out. Cool, filter with suction, wash the filter cake with a small amount of ethanol, and dry under reduced pressure to obtain 0.626 g of a yellow solid (Compound IVa), with a yield of 87.2%. Melting point: 249-250°C.

[0026] 1 H NMR (δ, DMSO-d 6): 2.77-2.84(m, 1H), 3.35-3.40(m, 1H), 5.25(dd, 1H, J=12.0Hz, 3.2Hz), 6.96(d, 1H, J=8.4Hz), 7.03(t , 1H, J=8.0, 16.0Hz), 7.27(t, 1H, J=8.0, 16.0Hz), 7.35(m, 2H), 7.38(d, 1H, J=7.2Hz), 7.44(t, 2H, J=7.2, 14.4Hz), 7.56(d, 2H, J=7.2Hz), 8.07(d, 1H, J=8.0Hz), 8.11(d, 2H, J=8.8Hz), 10.31(s, 1H) .

Embodiment 2

[0027] Example 2: Preparation of 4'-methoxyflavanone-4-(4-nitrophenyl)hydrazone (compound IVb)

[0028] The operation process is the same as in Example 1, except that flavanone is replaced by 4'-methoxyflavanone. A golden yellow solid (compound IVb) was obtained with a yield of 93.2%. Melting point: 237-238°C.

[0029] 1 H NMR (δ, DMSO-d 6 ): 2.80-2.87(m, 1H), 3.29-3.34(m, 1H), 3.75(s, 3H), 5.18(dd, 1H, J=12.0Hz, 2.8Hz), 6.93(d, 1H, J= 8.0Hz), 6.98(d, 2H, J=8.8Hz), 7.27(t, 1H, J=8.0, 16.0Hz), 7.32(m, 2H), 7.47(d, 2H, J=8.8Hz), 7.56 (d, 2H, J = 7.2Hz), 8.06 (d, 1H, J = 7.6Hz), 8.11 (d, 2H, J = 7.6Hz), 10.31 (s, 1H).

Embodiment 3

[0030] Example 3: Preparation of 5,7-dimethoxyflavanone-4-(4-nitrophenyl)hydrazone (compound IVc)

[0031] The operation process is the same as in Example 1, except that flavanone is replaced by 5,7-dimethoxyflavanone. An orange-red solid (compound IVc) was obtained with a yield of 89.3%. Melting point: 214-216°C.

[0032] 1 H NMR (δ, DMSO-d 6 ): 2.73-2.80(m, 1H), 3.30-3.35(m, 1H), 3.77(s, 3H), 3.92(s, 3H), 5.18(dd, 1H, J=12.0Hz, 3.2Hz), 6.23 (d, 1H, J = 2.4Hz), 6.30 (d, 1H, J = 2.4Hz), 7.29 (d, 2H, J = 2.4Hz), 7.39 (t, 1H, J = 7.2, 14.4Hz), 7.46 (t, 2H, J=7.2, 14.4Hz), 7.56(d, 2H, J=8.0Hz), 8.13(d, 2H, J=8.0Hz), 10.12(s, 1H).

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Abstract

The invention relates to poly-substitution flavane thiadiazoles class compound that uses neighbor hydroxy benzenes diketone and aromaticacid as raw material, taking concentrating and cyclization to gain flavanone class compounding that would react with substituted benzene to gain flavanone-4-phenylhydrazone, phenylhydrazone would cyclizating with thionyl chloride to form poly-substitution flavane thiadiazoles class compound. The invention has restraining function to kinds of tumor cell, and could be used in manufacturing anticancer medicine.

Description

technical field [0001] The invention belongs to a method for synthesizing organic compounds, and relates to a method for synthesizing thiadiazoline derivatives, in particular to multi-substituted flavanothiadiazoline compounds and their preparation methods, as well as their application in the preparation of antitumor drugs. Background technique [0002] Flavanone derivatives have antitumor effects. In 2001, C. Pouget et al. reported a series of flavanone derivatives with anti-tumor effects, including 7-methoxyflavanone, 5-methoxyflavanone and 5,7-dimethoxyflavanone Ketones are effective against breast cancer cell MCF-7, and its IC 50 The values ​​are 35.7, 35.7 and 36.0 μM, respectively. The structure of the flavanone derivatives provided in this article is relatively common, with no substitution on the aromatic ring or only oxygen-containing functional groups (hydroxyl and methoxy) substituted, and the author only carried out preliminary activity and structure studies on ...

Claims

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Application Information

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IPC IPC(8): C07D513/04A61P35/00
Inventor 胡永洲应华洲何俏军杨波
Owner ZHEJIANG UNIV
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