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Synthesis method of naphthofuran derivative, naphthofuran derivative and application

A synthetic method and derivative technology, applied in drug combination, antineoplastic drugs, organic chemistry, etc., can solve the problems of poor functional group tolerance, high cost of raw materials, cumbersome post-processing, etc., and achieve good yield, simple raw materials, and post-processing simple effect

Inactive Publication Date: 2020-07-03
LINYI UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] In summary, the existing problems in the prior art are: the synthesis method in the prior art has high cost of raw materials, long reaction time, high temperature, low reaction yield, poor functional group tolerance, cumbersome post-treatment, and negative impact on the environment. create pollution

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  • Synthesis method of naphthofuran derivative, naphthofuran derivative and application
  • Synthesis method of naphthofuran derivative, naphthofuran derivative and application
  • Synthesis method of naphthofuran derivative, naphthofuran derivative and application

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preparation example Construction

[0050] Such as figure 1 As shown, the embodiment of the present invention also proposes a synthetic method of naphthofuran derivatives as shown in formula (I), including:

[0051] S101, under the conditions of transition metal, additive, solvent, and reaction temperature, Boc-protected furyl aryl propargyl alcohol and aryl boronic acid are reacted.

[0052] S102, obtaining naphthofuran derivatives represented by formula (I).

[0053] In step S10, o-furyl aryl propargyl alcohol derivatives and aryl boronic acid are used as raw materials.

[0054] Its reaction process is shown in formula (II):

[0055]

[0056] where, where, R 1 , R 2 Respectively selected from phenyl, naphthyl, aryl substituted by electron-donating group, aryl substituted by electron-withdrawing group, alkyl, hydrogen; R 3 For halogen, methoxy, hydrogen.

[0057] In the embodiment of the present invention, R 1 , R 2 Respectively selected from phenyl, naphthyl, p-methylphenyl, p-methoxyphenyl, p-chlor...

Embodiment 1

[0074] Embodiment 1: the synthesis of IA

[0075]

[0076] o-furyl aryl propargyl alcohol derivatives, aryl boronic acid, catalyst, additive, and reaction solvent are respectively Boc-protected o-furan phenyl phenyl propargyl alcohol, phenylboronic acid, tetrakistriphenylphosphine palladium, cesium carbonate, 1, 4-dioxane. The dosages are 0.3mmol of Boc-protected o-furylphenylphenylpropargyl alcohol, 0.6mmol of phenylboronic acid, 0.006mmol of tetrakistriphenylphosphine palladium, 0.6mmol of cesium carbonate, and 3mL of 1,4-dioxane. React at 100°C for 2 hours, then cool to room temperature, concentrate, and perform column chromatography to obtain the target product formula (IA), a light yellow solid, with an isolation yield of 78%. Mp 194-196°C.

[0077] NMR data: 1 H NMR (CDCl 3 ,400MHz):δ5.96(s,1H),5.60(d,J=1.6Hz,1H),7.17(s,1H),7.25(d,J=6.0Hz,4H),7.30(t,J= 6.0Hz, 2H), 7.36(t, J=5.6Hz, 4H), 7.47(t, J=5.6Hz, 1H), 7.59(t, J=5.6Hz, 1H), 7.67(d, J=1.6Hz ,1H),7.80(d,J=6.4...

Embodiment 2

[0079] Embodiment 2: the synthesis of IB

[0080]

[0081] Chlorine-substituted o-furyl aryl propargyl alcohol derivatives, aryl boronic acid, catalyst, additive, and reaction solvent are respectively Boc-protected o-furyl phenyl phenyl propargyl alcohol, phenylboronic acid, tetrakistriphenylphosphine palladium, cesium carbonate, 1,4-Dioxane. The amounts used are respectively 0.3 mmol of Boc-protected chlorine-substituted o-furylphenylphenyl phenyl propargyl alcohol, 0.6 mmol of phenylboronic acid, 0.006 mmol of tetrakistriphenylphosphine palladium, 0.6 mmol of cesium carbonate, and 3 mL of 1,4-dioxane. React at 100°C for 2 hours, then cool to room temperature, concentrate, and perform column chromatography to obtain the target product formula (IB), a pale yellow solid, with an isolation yield of 72%. Mp 171-173°C.

[0082] NMR data: 1 H NMR (CDCl 3 ,400MHz):δ5.88(s,1H),6.53(s,1H),7.07(s,1H),7.17-7.34(m,11H),7.60-7.67(m,2H),8.23(s,1H ). 13 C NMR (CDCl 3 ,100MHz): δ54...

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Abstract

The invention belongs to the technical field of organic compounds and synthesis. The invention relates to the field of organic synthesis, and discloses a synthesis method of a naphthofuran derivative,the naphthofuran derivative and an application. An o-furan aryl propargyl alcohol derivative and arylboronic acid are used as raw materials, and Boc protected furan aryl propargyl alcohol and arylboronic acid react under the conditions of a transition metal, an additive, a solvent and a proper reaction temperature so that the naphthofuran derivative as shown in the formula (I) is obtained. The invention further provides an application of the naphthofuran derivative in preparation of antibacterial, anti-tumor and anti-virus active medicines. The preparation method provided by the invention hasthe advantages of cheap and easily available raw materials, high reaction yield, strong functional group tolerance, simple post-treatment, environmental friendliness and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and synthesis, and in particular relates to a synthesis method of naphthofuran derivatives, naphthofuran derivatives and applications. Background technique [0002] At present, the naphthofuran skeleton exists in a large number of natural products or drug molecules with physiological activity, showing various biological activities, including antifungal, antibacterial, insecticide, antiproliferative, cytotoxic, anti Oxidative, anti-inflammatory, anti-tumor, nuclear receptor regulator HNF4α, nicotinic acetylcholine receptor agonist (nAChR), etc. In addition, aromatic and furan skeletons also have good potential applications in materials chemistry, such as advanced pore transport materials and photosensitizers. Therefore, the synthesis of such substances has attracted widespread attention of organic synthesis workers. [0003] At present, there are mainly the following strategies for the ...

Claims

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Application Information

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IPC IPC(8): C07D307/92A61P31/00A61P31/12A61P35/00
CPCA61P31/00A61P31/12A61P35/00C07D307/92
Inventor 王程宇韩玉孔令凯
Owner LINYI UNIVERSITY
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