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Aza fused pentacyclic compound and preparation method thereof

A technology for cyclic compounds and compounds, applied in the field of aza-condensed pentacyclic compounds and their preparation, to achieve the effects of improving atom utilization efficiency, high yield, and easy operation

Inactive Publication Date: 2021-02-26
YANTAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Although the important physiological activities of Erythrina alkaloids have been reported, it is surprising that there are few reports on the change or derivation of its aza-fused tetracyclic ring structure. In order to further enrich the library of such compounds, the biological activity Research or drug development provides more selectivity, and there is an urgent need to develop new efficient and highly selective methods to synthesize derivatives of Erythrina alkaloids, especially the construction of aza-fused polycyclic skeleton structures

Method used

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  • Aza fused pentacyclic compound and preparation method thereof
  • Aza fused pentacyclic compound and preparation method thereof
  • Aza fused pentacyclic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1, the compound shown in preparation formula IIIa structural formula

[0032] The reaction formula is as follows:

[0033]

[0034] Under the protection of argon, add tetralone (25mmol), 3,4-dimethoxyphenethylamine (25mmol), toluene 50mL ( MS molecular sieve drying treatment) and magnetons, after the system was refluxed for 24 hours, the toluene solvent was removed by rotary evaporation to obtain the imine without other treatment, which was directly used in the next step reaction.

[0035] The obtained imine (5 mmol) was dissolved in 10 mL of DMF (dried over molecular sieves) under the protection of argon, and triethylamine (6 mmol) was added. After cooling the reaction system to -40°C, the corresponding acetophenone chloride (5.5 mmol) was slowly added. Then keep it at -40°C for 30 minutes. After the reaction was completed, 20 mL of saturated aqueous sodium bicarbonate solution was added to the system to quench the reaction, extracted with ethyl aceta...

Embodiment 2

[0042] Embodiment 2, the compound shown in preparation formula IIIb structural formula

[0043] The reaction formula is as follows:

[0044]

[0045] According to the similar method described in Example 1, the compound represented by formula IIIb was prepared, and the two-step yield was 70%.

[0046] The compound is a white solid:

[0047] Melting point mp: 140-140°C;

[0048] 1 H NMR (500MHz, DMSO-d 6 )δ7.71-7.59(m,3H),7.48(t,J=5.0Hz,2H),7.09(d,J=8.2Hz,1H),6.92-6.91(m,2H),6.82-6.80(m ,2H),6.66(d,J=2.6Hz,1H),5.59(dd,J=6.4,2.9Hz,1H),4.57-4.51(m,1H),3.76(s,3H),3.75(s, 3H),3.73(s,3H),3.27-3.22(m,1H),2.94-2.82(m,2H),2.65-2.52(m,2H),2.10-2.04(m,1H),1.85-1.76( m,1H);

[0049] 13 C NMR (126MHz, DMSO-d 6 )δ190.9, 167.1, 158.5, 149.1, 148.0, 135.6, 135.1, 133.5, 131.3, 131.2, 131.0, 129.4, 129.4, 129.1, 129.0, 121.5, 113.5, 113.4, 115.552, 109.6, 57.3, 59.1 ,25.7,22.9;

[0050] HRMS (ESI) Calcd.for C 29 h 29 NO 5 Na,[M+Na] + 494.1938. Found: 494.1938.

[0051] It can b...

Embodiment 3

[0052] Embodiment 3, the compound shown in preparation formula IIIc structural formula

[0053] The reaction formula is as follows:

[0054]

[0055] According to the similar method described in Example 1, the compound represented by formula IIIc was prepared, and the two-step yield was 67%.

[0056] The compound is a white solid:

[0057] Melting point mp: 147-148°C;

[0058] 1 H NMR (400MHz, DMSO-d 6 )δ7.71-7.65(m,1H),7.64-7.60(m,2H),7.51-7.45(m,2H),7.41(dd,J=8.0,2.1Hz,1H),7.22(d,J= 2.1Hz, 1H), 7.14(dd, J=8.0, 0.9Hz, 1H), 6.95-6.88(m, 2H), 6.81(dd, J=8.1, 2.0Hz, 1H), 5.64(dd, J=6.3 ,3.0Hz,1H),4.52(dt,J=13.5,7.5Hz,1H),3.75(s,3H),3.72(s,3H),3.24(ddd,J=13.4,7.4,5.6Hz,1H) ,2.97-2.77(m,2H),2.68-2.53(m,2H),2.15-2.07(m,1H),1.88-1.78(m,1H);

[0059] 13 C NMR (126MHz, DMSO-d 6 )δ190.5, 166.5, 148.7, 147.5, 135.9, 134.7, 134.2, 132.9, 132.2, 131.9, 130.8, 130.4, 129.8, 129.0, 128.9, 125.3, 121.0, 119.4, 113.50, 114.8, 5.2, 52.5 ,21.9;

[0060] HRMS (ESI) Calcd.for C 28 ...

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Abstract

The invention discloses a lenticin analogue containing an aza fused pentacyclic structure and a preparation method of the lenticin analogue. In the presence of a catalyst, a compound shown in a structural general formula III is firstly subjected to nucleophilic addition reaction to generate an imide positive ion intermediate, then the imide positive ion intermediate is captured by an electron-richunit indole ring in a molecule, and two rings are closed through one-step reaction. Under the catalytic condition of a Lewis acid, an aza fused pentacyclic compound shown in a formula I is obtained after the reaction is completed. Under the catalytic condition of a Brsted acid, an aza fused pentacyclic compound shown in a formula II is obtained after reaction. According to the preparation method,cheap and easily available raw materials and extremely simple operation are used, enamide is subjected to an intramolecular nucleophilic cascade reaction, and the lenticin analogue containing the azofused pentacyclic structure is prepared in a one-step, efficient and high-selectivity manner. The method has the advantages of mild reaction conditions, simple operation, high yield, high diastereoselectivity of the product, easy separation and purification, further derivatization of the product, and good application prospect.

Description

technical field [0001] The invention relates to an aza-condensed pentacyclic compound and a preparation method thereof, belonging to the field of pharmaceutical intermediates. Background technique [0002] As the dominant structure, aza-fused polycyclic skeleton structure widely exists in natural products, drugs, pesticides and other active molecules, including Strychnos, Aspidoperma, Amaryllicaceae, Erythrina. Among them, Erythrina Alkaloids have attracted extensive attention due to their unique aza-fused tetracyclic structure and potential physiological activities, and their efficient synthesis has also become a major research hotspot in academia and industry. [0003] Although the important physiological activities of Erythrina alkaloids have been reported, it is surprising that there are few reports on the change or derivation of its aza-fused tetracyclic ring structure. In order to further enrich the library of such compounds, the biological activity Research or drug d...

Claims

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Application Information

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IPC IPC(8): C07D471/10C07D471/20C07D491/20
CPCC07D471/10C07D471/20C07D491/20
Inventor 徐鑫明杨翰林李文忠
Owner YANTAI UNIV
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