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2, 7-bi-substituted fluorenone derivative and preparation method and application thereof

A derivative, two-substituted technology, applied in the field of medicinal chemistry, can solve problems such as limited application

Inactive Publication Date: 2015-04-01
WUHAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the symmetrical structure, alkyl side chain and tertiary amine functional group may limit the application of this class of compounds in antitumor

Method used

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  • 2, 7-bi-substituted fluorenone derivative and preparation method and application thereof
  • 2, 7-bi-substituted fluorenone derivative and preparation method and application thereof
  • 2, 7-bi-substituted fluorenone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Synthesis of 2-ethoxy-7-(2-hydroxyethoxy)-fluorenone (1a)

[0030] Add 2,7-dihydroxyfluorenone (10g, 0.047mol) into an aqueous solution of 200ml NaOH (4g, 0.1mol), stir until dissolved, add diethyl sulfate (9.2ml, 0.07mol) dropwise to the system, and react 5 After hours the precipitate was collected by filtration. The precipitate was dissolved in 80ml of DMSO, NaOH (2g, 0.05mol) and chloroethanol (4.1ml, 0.06mol) were added, and reacted overnight at 70°C. Pour the reaction system into 1M NaOH aqueous solution, collect the precipitate and wash and dry it, then dissolve the precipitate in 50ml CH 2 Cl 2 , the insoluble matter was filtered off and recrystallized in isopropanol to obtain 2-ethoxy-7-(2-hydroxyethoxy)-fluorenone. Orange solid, 30% yield. m.p.158-160°C.1H NMR (400MHz, CDCl3) δ: 7.27(s,1H),7.25(s,1H),7.13(dd,J=4.4,2.4Hz,2H),6.93(ddd,J= 10.4,8.2,2.4Hz,2H),4.12–4.08(m,2H),4.05(q,J=7.0Hz,2H),3.98(s,2H),1.42(t,J=7.0Hz,3H). 13C NMR(101MHz,CDCl3)δ:19...

Embodiment 2

[0031] Example 2: Synthesis of 2-ethoxy-7-(2-chloroethoxy)-fluorenone (1b)

[0032] 2-Ethoxy-7-(2-hydroxyethoxy)-fluorenone (2g, 0.007mol) was dissolved in 40ml of thionyl chloride and reacted at 60°C, monitored by TLC until the reaction was completed. The reaction system was poured into 1M NaOH aqueous solution, the precipitate was collected, washed and dried to obtain a crude product. Column chromatography gave 2-ethoxy-7-(2-chloroethoxy)-fluorenone. Orange solid, 90% yield. m.p.146.6-147.4°C.1H NMR(400MHz,CDCl3)δ:7.23(d,J=2.3Hz,1H),7.21(d,J=2.3Hz,1H),7.08(d,J=1.9Hz,2H ),6.88(ddd,J=14.3,8.1,2.5Hz,2H),4.19(t,J=5.8Hz,2H),3.99(q,J=7.0Hz,2H),3.75(t,J=5.8Hz ,2H),1.35(t,J=7.0Hz,3H).13C NMR(101MHz,CDCl3)δ:196.44,159.50,158.50,138.30,137.14,136.03,135.95,121.19,120.97,120.70,120.62,110.319,1 ,68.48,64.02,41.76,14.76.Anal.Calcd.for C17H15ClO3:C67.44,H4.99;Found C67.41,H5.01.MS(ESI):m / z[M-Cl]+calcd267.4 , found 267.3.

Embodiment 3

[0033] Example 3: Synthesis of 2-ethoxy-7-(2-dimethylaminoethoxy)-fluorenone (1c)

[0034] Dissolve 2-ethoxy-7-(2-chloroethoxy)-fluorenone (0.4g, 0.0013mol) in 40mlDMF, add potassium carbonate (0.5g, 0.0036mol) and aqueous dimethylamine (33% , 1.5ml, 0.01mol), 70 ° C for 24 hours, with saturated saline and CH 2 Cl 2Extract and separate the crude product by column chromatography to obtain 2-ethoxy-7-(2-dimethylaminoethoxy)-fluorenone. Orange solid, 85% yield. m.p.80-81.6°C.1H NMR (400MHz, CDCl3) δ: 7.19(d, J=8.1Hz, 2H), 7.06(d, J=7.0Hz, 2H), 6.89(d, J=8.0Hz, 1H ),6.84(d,J=8.0Hz,1H),4.03(t,J=5.4Hz,2H),3.98(dd,J=13.8,6.9Hz,2H),2.70(t,J=5.3Hz,2H ),2.30(s,6H),1.34(t,J=6.9Hz,3H).13C NMR(101MHz,CDCl3)δ:193.77,159.35,159.08,137.72,137.31,135.95,135.93,120.99,120.85,120.56, 120.49,110.19,110.14,66.31,63.98,58.11,45.77,14.76.Anal.Calcd.for C19H21NO3:C73.29,H6.80N4.50;Found C73.24,H6.82,N4.51.MS(ESI) :m / z[M+H]+calcd312.2,found312.0.

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Abstract

The invention relates to a 2, 7-bi-substituted fluorenone derivative and a preparation method and application thereof. The structural formula is shown as 2-hydroxy-3-amidopropyl, 2-amido, wherein R refers to halogenated hydrocarbon. The preparation method is simple and high in yield. Most compounds have good in-vitro antitumoral activity.

Description

technical field [0001] The invention relates to 2,7-disubstituted fluorenone derivatives and a preparation method and application thereof, belonging to the field of medicinal chemistry. technical background [0002] 2,7-(2-Diethylaminoethoxy)fluorenone (drug name: Tivolone), as the first synthetic small molecule interferon-inducing compound, has broad medicinal effects, such as antifungal, antiviral and The effect of anti-animal tumors can also enhance the body's humoral immunity. It is clinically used for anti-melanoma, inhibition of silicosis, and viral skin diseases, herpes zoster, and molluscum contagiosum. Tivolone has low toxicity, but it can cause nausea, vomiting, fatigue, dizziness, headache and other symptoms, and it has certain toxicity to the heart when the dose is too large. The compounds involved in the existing structure-activity relationship studies basically retain the structural characteristics of the alkyl side chain and two tertiary amine functional grou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/24C07C217/38C07C213/02C07D295/088C07D249/08C07D249/04C07D233/60C07C49/755A61K31/138A61K31/4545A61K31/4196A61K31/4178A61K31/4192A61P35/00
Inventor 胡先明周丁山庹伟刘鹏肖玉玲周小菊
Owner WUHAN UNIV
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