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Substituted benzylidene tetralone derivatives and preparation method and applications

A technology of dihydronaphthalene and trimethoxy, which is applied in the field of substituted benzylidene tetralone derivatives and its preparation, can solve the problems that the application of substituted benzylidene tetralones has not been reported, and achieve an improvement Water-soluble, bioactivity-enhancing effect

Inactive Publication Date: 2015-05-27
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But about substituted benzylidene tetralone derivatives of the present invention and preparation method, application also do not see report at present

Method used

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  • Substituted benzylidene tetralone derivatives and preparation method and applications
  • Substituted benzylidene tetralone derivatives and preparation method and applications
  • Substituted benzylidene tetralone derivatives and preparation method and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1: 2-(3,4,5-trimethoxyphenyl) ethyl acetate (1).

[0070] 2-(3,4,5-trimethoxyphenyl)acetic acid (90.5g, 0.4mol), absolute ethanol (120mL) and concentrated H 2 SO 4 (8mL) was added to toluene (500mL), refluxed overnight, and the water separator was removed. After the reaction was completed, it was concentrated under reduced pressure, extracted with EtOAc (400 mL), washed successively with 1N aqueous NaOH (50 mL) and brine, and Na 2 SO 4 Drying and concentration under reduced pressure gave compound 1 as light yellow oil (100.6 g, 99% yield). 1 H NMR (300MHz, CDCl 3 )δ6.52(s,2H),4.18(q,J=7.1Hz,2H),3.87(s,6H),3.85(s,3H),3.56(s,2H),1.29(t,J=7.1 Hz,3H).ESI-MS m / z=255.24[M+1] + .

Embodiment 2

[0071] Example 2: 2-(2-formyl-3,4,5-trimethoxyphenyl) ethyl acetate (2).

[0072] Put 70mL of freshly distilled POCl into a 1L three-neck flask 3 (0.76 mol) and N-methylformanilide (102.73 g, 0.76 mol) were vigorously stirred to produce a yellow solid. Then inject ethyl 2-(3,4,5-trimethoxyphenyl)acetate (1) (97.0g, 0.38mol) and stir at room temperature for 40 hours. The resulting red thick substance is slowly poured into 2000mL of crushed ice , a yellow crude product was precipitated, filtered, and recrystallized from acetone to obtain white needle crystals 2 (65.5g, 61% yield). 1 H NMR (300MHz, CDCl 3 )δ10.34(s,1H),6.52(s,1H),4.18(q,J=7.1Hz,2H),4.01(s,3H),3.93(s,3H),3.92(s,2H), 3.88(s,3H),1.29(t,J=7.1Hz,3H).ESI-MS m / z=283.14[M+1] + .

Embodiment 3

[0073] Example 3: Ethyl 3-(6-(2-ethoxy-2-carbonylethyl)-2,3,4-trimethoxyphenyl)acrylate (3).

[0074] Ethyl 2-(2-formyl-3,4,5-trimethoxyphenyl)acetate (2) (23.0g, 0.081mol) and ethoxyformylmethylenetriphenylphosphine (30.0g, 0.086mol) was dissolved in dry toluene (180mL), under nitrogen protection, and refluxed for 20 hours. Cool to room temperature and distill under reduced pressure to obtain a pale yellow solid, which was dissolved in diethyl ether (180 mL), heated to reflux for half an hour, and filtered to remove the solid. The filtrate was concentrated, passed through a neutral aluminum oxide chromatography column, and the mobile phase PE:EA=5:1 was washed to obtain the product 2 as a white solid (26.2 g, 92% yield). 1 H NMR (300MHz, CDCl 3 )δ7.76(d, J=16.1Hz, 1H), 6.63(s, 1H), 6.57(d, J=16.1Hz, 1H), 4.27(q, J=7.2Hz, 2H), 4.20(q, J=7.3Hz, 2H), 3.90(s, 3H), 3.89(s, 3H), 3.88(s, 3H), 3.72(s, 2H), 1.35(t, J=7.1Hz, 3H), 1.29( t,J=7.1Hz,3H).ESI-MS m / z=375.1[M+Na] + .

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PUM

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Abstract

The invention relates to substituted benzylidene tetralone derivatives and a preparation method and application. The chemical structural formula of the substituted benzylidene tetralone derivatives is shown in the formula (1) in the specification, and in the formula (1), X represents CHOH or C=O, and R represents any one of H, OH, F, Cl, CN, CONH2, NO2, CH3, OCH3 and NH2. In the synthetic route, any substitution group can be introduced into two benzene rings, thus eliminating the limit on organic synthesis for finding out compounds with better activity. After water-soluble groups such as amino and the like are introduced, the water solubility can be greatly improved compared with a pilot compound CA-4, and the research of druggability is facilitated. In addition, after amino, hydroxyl and the like are introduced, not only can the bioactivity be improved, but also a prodrug can be prepared on the basis of the group, and the in-vivo activity study can be favorably conducted. The derivatives have the effects of treating ovarian cancer, colon cancer, thyroid cancer and leukemia.

Description

technical field [0001] The invention relates to the technical field of medicines, specifically, substituted benzylidene tetralone derivatives, a preparation method and an application thereof. Background technique [0002] Tumors, especially malignant tumors, have seriously threatened human health. According to the "Global Cancer Report 2014" released by the World Health Organization (WHO), the incidence of cancer in developing countries in Africa, Asia, and Central and South America is the most severe. In 2012, there were 14 million new cancer cases and 8.2 million deaths worldwide. Among them, China added 3.07 million cancer patients and caused about 2.2 million deaths, accounting for 21.9% and 26.8% of the global total respectively. The report predicts that global cancer cases will show a rapid growth trend, from 14 million in 2012 to 19 million in 2025 and 24 million in 2035. Although antineoplastic drugs have made great contributions to prolonging the survival time of...

Claims

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Application Information

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IPC IPC(8): C07C49/755C07C45/68C07C255/56C07C253/30C07C235/84C07C231/12C07C205/45C07C201/12C07C211/45C07C209/68C07C43/23C07C41/26C07C255/54C07C235/60C07C205/37A61P35/00A61P35/02
CPCC07C43/23C07C49/755C07C205/37C07C205/45C07C217/84C07C225/22C07C235/60C07C235/84C07C255/54C07C255/56C07C2602/10
Inventor 朱驹周有骏郑灿辉蒋骏航吕加国刘嘉周浩
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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