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Isoflavone compound, its preparation method, and its application in preparation of antiviral or antitumor drugs

A compound and selected technology can be used in anti-tumor drugs, anti-viral agents, active ingredients of heterocyclic compounds, etc., and can solve problems such as increasing difficulty, increasing investment in research and development, and prolonging the time for research and development of new drugs.

Inactive Publication Date: 2012-08-01
SHANGHAI RUIGUANG BIOCHEM TECH DEV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Nevertheless, from the perspective of the global new drug research and development market, due to people's higher and higher requirements for the quality of life, the quality requirements for new drugs are bound to become higher and higher. Toxic and side effects, negative effects on people's health are minimized
This greatly prolongs the time for new drug research and development, increases the investment in research and development, and increases the difficulty of developing new drugs

Method used

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  • Isoflavone compound, its preparation method, and its application in preparation of antiviral or antitumor drugs
  • Isoflavone compound, its preparation method, and its application in preparation of antiviral or antitumor drugs
  • Isoflavone compound, its preparation method, and its application in preparation of antiviral or antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: Preparation of Compound 2 in Scheme 1

[0041] Sodium block (12.7g, 550mmol) was put into dried xylene (100mL), heated to melt, cooled to room temperature, poured out xylene, washed with anhydrous ether (50mL×2). Sodium was placed in anhydrous ether (100 mL), stirred vigorously, and cooled to 0°C. Under nitrogen protection, an anhydrous ether solution (100 mL) of paeonol 1 (30.7 g, 185 mmol) and ethyl formate (41.0 g, 550 mmol) was slowly added dropwise to the mixture. After the addition was complete, stirring was continued at 0°C for 1 hour, then warmed to room temperature overnight. The reaction solution was poured into ice water (400 mL) containing 12.5% ​​acetic acid, extracted with ethyl acetate (200 mL×3), the organic phases were combined, and the solvent was evaporated to dryness under reduced pressure to obtain 33.0 g of a light yellow solid with a yield of 92%. It was confirmed that the obtained compound was compound 2 in Scheme 1.

[0042] 1 ...

Embodiment 2

[0043] Embodiment 2: the preparation of compound 3

[0044] Mix 3-(2-hydroxy-4-methoxyphenyl)-3-carbonylpropionaldehyde 2 (33g, 170mmol) obtained in Example 1 with acetic acid (150mL) and concentrated hydrochloric acid (10mL), Heat for half an hour. The acetic acid was distilled off under reduced pressure, water (300 mL) was added and adjusted to pH=8 with sodium bicarbonate. Extracted with dichloromethane (200 mL×3), combined the organic phases, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain 28.0 g of a pale yellow solid with a yield of 93%. It was confirmed that the obtained compound was compound 3 in Scheme 1.

[0045] 1 H NMR (300MHz, CDCl 3 ): 3.90 (s, 3H, CH 3 ), 6.28 (d, 1H, J=6.3Hz, O=C-CH=C), 6.84 (d, 1H, J=2.4Hz, ArH), 6.98 (dd, 1H, J=2.4Hz, 9.0Hz, ArH), 7.78 (d, 1H, J=6.3Hz, C=CH-O), 8.12(d, 1H, J=9.0Hz, ArH); ESI-MS m / z: 177 (M+H) + .

Embodiment 3

[0046] Embodiment 3: the preparation of compound 4

[0047] The 7-methoxybenzopyrone 3 (4.3g, 24.4mmol) and piperidine (6.2mL, 62.5mmol) obtained in Example 2 were dissolved in methanol (50mL), refluxed for 3 hours, and evaporated to dryness under reduced pressure Solvent was used to obtain 6.3 g of yellow solid with a yield of 99%. It was confirmed that the obtained compound was compound 4 in scheme 1.

[0048] 1 H NMR (300MHz, CDCl 3 ): 1.68 (m, 6H, 3CH 2 ), 3.39 (m, 4H, 2CH 2 ), 3.81 (s, 3H, CH 3 ), 5.78 (d, 1H, J=12.3Hz, O=C-CH=C), 6.37 (dd, 1H, J=2.4Hz, 9.0Hz, ArH), 6.41 (d, 1H, J=2.4Hz, ArH), 7.58(d, 1H, J=9.0Hz, ArH), 7.81(d, 1H, J=12.3Hz, C=CH-N), 14.5(s, 1H, OH); ESI-MS m / z : 262(M+H) + .

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Abstract

The invention relates to an isoflavone compound, its preparation method, and its application in the preparation of antiviral or antitumor drugs, and concretely relates to a compound with a structural formula represented by formula (I). In the formula (I), R1 is hydrogen or C1-6 alkyl; X is -O-, -NH-, -CH=CH-, or ethinyl, or R2 is directly connected with benzopyran; R2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted heteroaryl, C1-16 alkyl, C1-16 alkyloxy, C1-16 alkyloxycarbonyl, or substituted or unsubstituted benzoyloxy; the heteroaryl is selected from groups derived from a five or six-membered heterocycle or a fused heterocycle containing one or two hetero atoms of N, O or S, and is selected but not limited to pyridyl, benzopyridyl, or groups derived from phenoxathiin, thiophene, oxazole and benzopyridine; and above substituent is selected from halogen, cyan, nitro, hydroxy, amino, C1-6 monosubstituted or disubstituted amino, C1-16 alkyl, halogenated C1-6 alkyl, C2-6 alkenyl, C6-12 arylalkenyl, C1-16 alkyloxy, C1-16 carboxyl, C1-16 alkyloxycarbonyl, C1-16 alkylcarbonyl, and substituted or unsubstituted phenoxyl. The invention also provides the preparation of the compound.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry. The present invention particularly relates to a class of isoflavone compounds with antiviral and antitumor activities. The present invention also relates to the preparation method of such compounds. The present invention also relates to the use of such compounds in the preparation of therapeutic antiviral or Application in antitumor drugs. Background technique [0002] Malignant tumor is a common and frequently-occurring disease that seriously threatens human health. The mortality rate caused by malignant tumors is the second highest among all diseases, second only to cardiovascular and cerebrovascular diseases. Tumor treatment methods include surgery, radiation therapy, and drug therapy (chemotherapy), but chemotherapy is still the main method to a large extent. [0003] Antineoplastic drugs refer to drugs against malignant tumors, that is, anticancer drugs. Since nitrogen mustard wa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36C07D409/04C07D411/04C07D311/22C07D405/12C07D407/12A61K31/352A61K31/381A61K31/39A61K31/4433A61K31/438A61K31/422A61P35/00A61P1/16A61P1/00A61P31/20
Inventor 董环文张明刚汪元璋张峥牛春娟
Owner SHANGHAI RUIGUANG BIOCHEM TECH DEV
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