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
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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, h

Method used

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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

Examples

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Example Embodiment

[0050] Such as figure 1 As shown, the embodiment of the present invention also proposes a method for synthesizing the naphthofuran derivative represented by formula (I), including:

[0051] In S101, the furan aryl propargyl alcohol protected by Boc reacts with the aryl boronic acid under suitable conditions of transition metal, additives, solvent, and reaction temperature.

[0052] S102, the naphthofuran derivative represented by formula (I) is obtained.

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

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

[0055]

[0056] Among them, 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 It is halogen, methoxy, hydrogen.

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

Example Embodiment

[0074] Example 1: Synthesis of IA

[0075]

[0076] O-furan aryl propargyl alcohol derivatives, aryl boronic acid, catalysts, additives, and reaction solvents are Boc protected o-furan phenyl phenyl propargyl alcohol, phenylboronic acid, tetrakistriphenylphosphine palladium, cesium carbonate, 1, 4-Dioxane. The dosages were 0.3 mmol of Boc-protected o-furanphenyl phenyl propargyl alcohol, 0.6 mmol of phenylboronic acid, 0.006 mmol of palladium tetrakistriphenylphosphine, 0.6 mmol of cesium carbonate, and 3 mL of 1,4-dioxane. The reaction was carried out at 100°C for 2 hours, then cooled to room temperature, concentrated, and column chromatography was used to obtain the target product formula (IA) as a pale yellow solid with an isolated yield of 78%. Mp 194-196°C.

[0077] NMR data: 1 H NMR(CDCl 3 , 400MHz): δ 5.96 (s, 1H), 5.60 (d, J = 1.6 Hz, 1H), 7.17 (s, 1H), 7.25 (d, J = 6.0 Hz, 4H), 7.30 (t, J = 6.0Hz, 2H), 7.36 (t, J = 5.6 Hz, 4H), 7.47 (t, J = 5.6 Hz, 1H), 7.59 (t, J = 5.6...

Example Embodiment

[0079] Example 2: Synthesis of IB

[0080]

[0081] Chlorine-substituted o-furan aryl propargyl alcohol derivatives, aryl boronic acid, catalysts, additives, and reaction solvents are Boc-protected o-furan phenyl phenyl propargyl alcohol, phenylboronic acid, tetrakistriphenylphosphine palladium, cesium carbonate, 1,4-Dioxane. The dosages are respectively 0.3 mmol of Boc-protected chlorine-substituted o-furan phenyl phenyl propargyl alcohol, 0.6 mmol of phenylboronic acid, 0.006 mmol of tetratriphenylphosphine palladium, 0.6 mmol of cesium carbonate, and 3 mL of 1,4-dioxane. The reaction was carried out at 100°C for 2 hours, then cooled to room temperature, concentrated, and column chromatographed to obtain the target product formula (IB) as a pale yellow solid with an isolated 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): δ54.75,107.11,119.23,...

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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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