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Method for preparing o-dihydroxyflavone-selenium complexes and medical use

A technology of dihydroxyflavonoids and complexes, which is applied in the fields of natural medicinal chemistry, drug synthesis and pharmacology, and can solve problems such as anti-tumor activity research that has not been reported yet

Inactive Publication Date: 2008-03-26
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis of some transition metal complexes of rutin has been reported, but the synthesis and antitumor activity of rutin-selenium complexes have not been reported

Method used

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  • Method for preparing o-dihydroxyflavone-selenium complexes and medical use
  • Method for preparing o-dihydroxyflavone-selenium complexes and medical use

Examples

Experimental program
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Effect test

Embodiment 1

[0014] Embodiment 1: the preparation of rutin-selenium complex

[0015] Add 1 g (0.001641 mol) of rutin into dry 20 ml of pyridine, stir, drop into 0.5 ml of selenium oxychloride, dry it, and react at room temperature for 48 hours, add ether to precipitate a precipitate, wash repeatedly with ether and chloroform to obtain a precipitate, Vacuum freeze-drying to obtain a brown rutin-selenium complex. Weighed 1.332g, yield 51.5%. The newly synthesized compounds were identified by various physical methods, including 1 HNMR, MS and elemental analysis. Its structure is as follows (see accompanying drawing 2 of specification sheet):

[0016] Figure 2 Rutin-selenium complex

[0017] mp: 185.0-189.0℃.IR(KBr)3219cm -1 (O-H), 1654cm -1 (C=O), 1610, 1537cm -1 (C=C), 1198cm -1 (C-O-C), 750cm -2 (C-H), 680cm -2 (Se-O). 1 H NMR (CDCl 3 , 300MHz), δ (ppm): 11.68 (s, 1H, 5-OH), 10.56 (s, 1H, 7-OH), 7.53 (d, 1H, 2'-H), 7.38 (d, 1H, 5 '-H), 6.70 (d, 1H, 6'-H), 6.13 (d, 1H, 8-H), 5.9...

Embodiment 2

[0018] Embodiment 2: the preparation of quercetin-selenium complex

[0019] Add 2g (0.006623mol) of quercetin into dry 30ml of pyridine, stir, drop into 2.0ml of selenium oxychloride, dry, and react at room temperature for 48h, add ether to precipitate a precipitate, wash repeatedly with ether and chloroform to obtain a precipitate , vacuum freeze-drying, and finally a brown quercetin-selenium complex. Weighed 2.437g, yield 47.8%. Its structure is as follows (see accompanying drawing 3 of specification sheet):

[0020] Figure 3 Quercetin-selenium complex

[0021] mp: 315.0-318.0℃.IR(KBr) 1651cm -1 (C=O), 1606, 1530cm -1 (C=C), 1206cm -1 (C-O-C), 755cm -1 (C-H), 680cm -1 (Se-O). 1 H NMP (CDCl 3 , 300MHz), δ (ppm) 11.88 (s, 1H, 5-OH), 10.50 (s, 1H, 7-OH), 10.26 (s, 1H, 3-OH), 7.60 (d, 1H, 2'- H), 7.29(d, 1H, 5'-H), 6.71(d, 1H, 6'-H), 6.18(d, 1H, 8-H), 5.98(d, 1H, 6-H), MS (m / z): 378.1 (M - +Se). Molecular formula: C 15 h 8 o 7 Se, elemental analysis: Calcd for (%)...

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Abstract

The present invention relates to synthesis process and medicinal use of o-dihydroxyflavone-selenium complex. The o-dihydroxyflavone-selenium complex in the structure as shown may be applied in preparing health product, pesticide, plant growth regulator, feed additive, immunomodulator, antitumor medicine, antibacterial medicine, etc.

Description

technical field [0001] The invention belongs to the technical fields of natural medicinal chemistry, drug synthesis and pharmacology, and specifically relates to the synthesis of flavone-selenium complexes and the screening of the compound's inhibitory activity on human tumor cell growth. It can be used to prepare health products, pesticides, insecticides, plant growth regulators, feed additives, immunomodulators, antitumor drugs, and antibacterial drugs. Background technique [0002] Selenium has a variety of special functions on human health. Nowadays, selenium has been recognized by the United Nations as an essential trace element for the human body. Many diseases such as tumors, aging, and low immunity are related to the lack of selenium in the body. It is of great significance to improve the body's immunity, inhibit aging and prevent diseases. Compared with inorganic selenium, organic selenium has the characteristics of high bioavailability, strong biological activity,...

Claims

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Application Information

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IPC IPC(8): C07D345/00C07H17/07A61K31/7048A61K31/352A61P35/00A61P31/04A01N55/00A01P7/00A01P21/00A23K1/16C07D311/30
Inventor 仇佩虹吴建章周鹏叶发青林丽郭平
Owner WENZHOU MEDICAL UNIV
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