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Aromatic polyketone compound and preparation method thereof

A technology of polyketide compounds and compounds, applied in organic chemistry and other fields, can solve problems such as complex chemical structure, no chemical synthesis, and difficult chemical synthesis

Active Publication Date: 2018-06-15
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As new natural statins, benastatin G and benastatin J have broad application prospects. The chemical structure of benastatin natural products is complex, and chemical synthesis is relatively difficult. At present, benastatin compounds are mainly synthesized by chemical separation. For example, benastatin G was isolated from Streptomyces during heterologous expression of benastatin biosynthetic gene cluster by Christian Hertweck et al.; and benastatin J was obtained from benastatin G through Methylation and elimination of one molecule of water conversion, there is no report on the chemical synthesis of benastatin natural products, let alone the chemical synthesis of benastatin G and benastatin J

Method used

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  • Aromatic polyketone compound and preparation method thereof
  • Aromatic polyketone compound and preparation method thereof
  • Aromatic polyketone compound and preparation method thereof

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Experimental program
Comparison scheme
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Embodiment 1

[0106] Embodiment 1: Preparation of the aromatic polyketide compound of the present invention

Embodiment 11

[0107] Compound shown in embodiment 1.1 preparation formula 2:

[0108] Step a: prepare the compound shown in formula 7:

[0109]

[0110] The compound of formula 6 (3.51g, 19.49mmol) was dissolved in N,N-dimethylformamide (20mL), and then phosphorus oxychloride (2.68mL, 29.23mmol) was slowly added dropwise at 0°C under nitrogen protection, After the dropwise addition, stir the reaction at 90°C for 3 hours to end the reaction. After the reaction solution is cooled to room temperature, it is slowly poured into ice water. The resulting mixed solution is adjusted to pH 10 with 20 wt% sodium hydroxide solution, and then extracted with ether. , the organic phases were combined, and the organic phase obtained was washed once with saturated sodium bicarbonate solution and saturated brine successively, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure until no solution was distilled off, and the residue was analyzed by column ch...

Embodiment 12

[0138] Embodiment 1.2 prepares the compound shown in formula 3:

[0139] Step A: prepare the compound shown in formula 13:

[0140]

[0141] The compound of formula 12 (8.08g, 25.58mmol) was dissolved in N,N-dimethylformamide (64mL), and potassium carbonate (7.78g, 56.27mmol) and dimethyl sulfate (5.09mL, 53.72mmol) were added, Then react at 60°C for 21.5 hours to end the reaction, cool the reaction liquid to room temperature, quench with saturated ammonium chloride solution, extract with ethyl acetate, combine the organic phases, and wash the organic phases twice with water, saturated chlorinated Sodium was washed once, dried with anhydrous sodium sulfate, filtered, concentrated, and the residue was separated by column chromatography (5% ethyl acetate / petroleum ether) to obtain the compound of formula 13 (7.74g, yield rate 88%), Rf= 0.56 (20% ethyl acetate / petroleum ether).

[0142] Tested: 1 H NMR (300MHz, CDCl 3 )δ6.46(s,2H),3.91(s,3H),3.83(s,6H)ppm;

[0143] 13 C ...

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Abstract

The invention discloses an aromatic polyketone compound and a preparation method thereof. The aromatic polyketone compound is of a chemical structure of formula I as shown in the specification, in theformula, R1, R2 and R3 are respectively independently selected from C1-C8 alkyl, and R4 is selected from hydrogen or C1-C8 alkyl. By adopting the aromatic polyketone compound disclosed by the invention, Benastatin G, Benastatin J, derivatives thereof or natural products of similar structures can be synthesized; in addition, the preparation method of the aromatic polyketone compound disclosed by the invention has the advantages of being simple to operate, safe and free of pollution, free of special requirements on equipment, low in production cost, and the like, and has very high practical values for achieving industrial preparation of aromatic polyketone compounds.

Description

technical field [0001] The invention relates to an aromatic polyketone compound and a preparation method thereof, and belongs to the technical field of chemical drug synthesis. Background technique [0002] Aromatic polyketides usually have good biological activity, for example: benastatin G (Benastatin G) and benastatin J (Benastatin J) in benastatin (Benastatin) drugs, studies have shown that these compounds have the ability to prevent The activity of malignant cell proliferation, for example, benastatin G exhibits good biological activity against human cervical cancer cells, its IC50 is 9.4 μg / mL, and the structural formulas of the above compounds are as follows: [0003] [0004] As new natural statins, benastatin G and benastatin J have broad application prospects. The chemical structure of benastatin natural products is complex, and chemical synthesis is relatively difficult. At present, benastatin compounds are mainly synthesized by chemical separation. For exampl...

Claims

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Application Information

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IPC IPC(8): C07D311/78
CPCC07D311/78
Inventor 辛坤云陈彦宇杨鲍潮高栓虎
Owner EAST CHINA NORMAL UNIV