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Total synthesis method of chloromycin A and analogue

A technique for griseogreenin and analogs, which is applied in the field of total synthesis of griseogreenin A and analogs, and achieves the effects of simple reaction steps, mild reaction conditions and wide adaptability

Inactive Publication Date: 2017-06-13
QINGDAO TECHNOLOGICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, the chemical total synthesis of Giseoviridin A has not been reported in the literature, so seeking a kind of preparation is simple, the raw material is easy to get, the total synthesis method of Giseoviridin A and analogues with friendly preparation conditions has good social and economic benefits

Method used

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  • Total synthesis method of chloromycin A and analogue
  • Total synthesis method of chloromycin A and analogue
  • Total synthesis method of chloromycin A and analogue

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of 4-methoxy-1-acetoxy-9,10-anthraquinone

[0034] 1-Hydroxy-4-methoxy-9,10-anthraquinone (2.0 g, 7.87 mmol) was dissolved in 100 mL of dichloromethane, and triethylamine (6.04 mL, 43.29 mmol) and diethyl Acyl chloride (2.23mL, 31.48mmol), raised to room temperature and continued stirring for 1 hour, concentrated under reduced pressure, extracted and filtered with dichloromethane, washed the extract with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the remaining The product was separated by flash column chromatography (V (petroleum ether (60~90°C): V (ethyl acetate) = 2:1, R f =0.275), to obtain 2.0 g of 4-methoxy-9,10-anthraquinone-1-acetate, with a yield of 86%. Orange-yellow solid, M.p.: 185°C, 1 HNMR (CDCl 3 ,400MHz,23℃),δ8.2(m,1H),8.1(m,1H),7.7(m,2H),7.3(m,2H),4.0(s,3H),2.5(s, 3H) ; MS (APCI) for C 17 h 12 o 5 (M+H + ): 297.1.

Embodiment 2

[0035] Example 2: Preparation of 4-methoxy-1-benzoyloxy-9,10-anthraquinone

[0036] Dissolve 1-hydroxy-4-methoxy-9,10-anthraquinone (2g, 7.87mmol) in 100mL of dichloromethane, add triethylamine (6.04mL, 43.3mmol) and benzoyl chloride successively under ice-cooling (3.63mL, 31.5mmol), after continuing to react at room temperature for 2 hours, washed with saturated brine, concentrated under reduced pressure, and the residue was separated by flash column chromatography (V (petroleum ether (60-90°C): V (ethyl acetate) = 2:1, R f =0.35), to obtain 2.45 g of orange-yellow solid 4-methoxy-1-benzoyloxy-9,10-anthraquinone with a yield of 87%. Orange-yellow solid, M.p.: 214°C, 1 H NMR (CDCl 3 ,400MHz,23℃), δ8.31(dd,2H),8.25(d,1H),8.11(d,1H),7.78(m,3H),7.61(m,2H),7.52(d,1H) ,7.45(d,1H),4.10(s,3H); MS(APCI) for C 22 h 14 o 6 (M+H + ): 358.9.

Embodiment 3

[0037] Example 3: Preparation of 6-methoxy-(1-benzoyl)naphtho[1,2,3-de]benzopyran-2,7-dione

[0038] Under nitrogen, anhydrous potassium carbonate (120 mg, 0.85 mmol), ethyl benzoylacetate (43 μL, 0.225 mmol), 1-acetic acid-4-methoxyanthraquinone ester (50 mg, 0.17 mmol) and DMSO ( 2.0 mL), after reacting at 40°C for 24 hours, add 10 mL of water, extract with dichloromethane (3×30 mL), combine the extracts, dry over anhydrous sodium sulfate, filter, concentrate under reduced pressure, and the residue is separated by flash column chromatography ( V (petroleum ether (60-90°C): V (ethyl acetate) = 2:1, Rf = 0.13), to obtain 6-methoxy-1-benzoylnaphthyl[1,2,3-de]benzene Pyran-2,7-dione 72 mg, yield 55%. Tan solid, M.p.: 224°C, 1 H NMR (CDCl 3 ,400MHz,23℃),δ8.47(dd,1H),8.07(d,2H),7.85(d,1H),7.73(m,3H),7.55(m,2H),7.47(m,2H) ,4.14(s,3H); MS(APCI) for C 24 h 14 o 5 (M+H + ): 383.1.

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Abstract

The invention belongs to the technical field of chemical synthesis and relates to a total synthesis method of chloromycin A and an analogue. The total synthesis method comprises the following steps: taking a 1-hydroxy anthraquinone compound as a starting raw material, protecting hydroxyl through acylation, then generating a 9-anthrone lactone compound with beta-keto ester through Knoevenagel norfloxacin reaction, and finally performing demethylating reaction to obtain final products, namely the chloromycin A and the analogue. The total synthesis method has the advantages that the raw material is easy to obtain, reaction steps are simple, reaction conditions are mild, the post-treatment is convenient, the adaptability is wide, and the like; the synthesized chloromycin A and analogue can be used for developing a novel antitumor drug.

Description

[0001] Technical field: [0002] The invention belongs to the technical field of chemical synthesis, and relates to a total synthesis method of griseovirmycin A and analogues; using 1-hydroxyanthraquinone compounds as starting materials, acylation, Knoevenagel ring condensation reaction and demethylation The final product griseovirmycin A and analogues are obtained. [0003] Background technique: [0004] Giseoviridin A is a compound with a novel anthraquinone lactone skeleton structure isolated from a secondary metabolite produced by Aspergillus glaucus HB1-19. A variety of cancer cells, such as human lung cancer A549 cells, human leukemia HL-60 cells, human liver cancer BEL-7402 cells, and mouse leukemia P388 cells, have a strong inhibitory effect on proliferation, as a new anti-tumor lead with anthraquinone structure It may exhibit different characteristics from anthracycline antineoplastic drugs such as doxorubicin in terms of efficacy and cardiotoxicity; since the content...

Claims

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Application Information

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IPC IPC(8): C07D311/78A61P35/00
CPCC07D311/78
Inventor 谭伟强夏岩
Owner QINGDAO TECHNOLOGICAL UNIVERSITY
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