Imidazaphenanthridine compound as well as preparation method and application thereof

An imidazo, compound technology, applied in the field of compound synthesis, can solve the problems of low substrate diversity and low yield, and achieve the effects of wide application range, high reaction efficiency and mild reaction conditions

Active Publication Date: 2020-03-24
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above method requires metal catalysis and the yield is low, and the substrate diversity is not high.

Method used

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  • Imidazaphenanthridine compound as well as preparation method and application thereof
  • Imidazaphenanthridine compound as well as preparation method and application thereof
  • Imidazaphenanthridine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 4,11-diphenyl-1,2-dihydrobenzo[f]imidazo[2,1-α][2,7]quinoline

[0043]

[0044] 3-(2-Aminophenyl)-1-phenylprop-2-en-1-one (0.6mmol, 133.8mg) and 2-(imidazolidine-2-ylidene)-1-phenylethane -1-ketone (0.5mmol, 94mg) was added to 1mL of glacial acetic acid. After the addition was complete, it was reacted at room temperature for 24h, and observed by spotting. After the reaction was completed, NaOH (1M) was added to the reaction solution for neutralization, and then extracted through the column to obtain a yellow solid.

[0045] Yellow solid, m.p.>250℃, 1 H NMR (500MHz, CDCl 3 )δ8.40(d, J=8.0Hz, 1H), 8.24(d, J=8.5Hz, 1H), 7.98–7.93(m, 1H), 7.80–7.72(m, 5H), 7.65–7.59(m ,6H),4.64–4.57(m,2H),4.22–4.15(m,2H). 13 C NMR (125MHz, CDCl 3 )δ159.3, 156.3, 149.4, 147.3, 142.9, 142.3, 135.5, 130.9, 130.3, 129.9, 129.2, 129.0, 128.1, 127.9, 126.6, 123.3, 121.8, 111.5, 98.3, 53.0, 49.1: HRMS (ESI). z calcd for (C 26 h 20 N 3 +H) + :374.1657; found: 374.1660.

Embodiment 2

[0046] Example 2 11-phenyl-4-(p-tolyl)-1,2-dihydrobenzo[f]imidazo[2,1-α][2,7]quinoline

[0047]

[0048] The synthetic steps are the same as in Example 1, except that 2-(imidazolidine-2-ylidene)-1-phenylethane-1-ketone is replaced by 2-(imidazolidine-2-ylidene)-1-(p-toluene base) ethyl-1-one to give a yellow solid.

[0049] Yelbow solid, m.p.234.1-235℃, 1 H NMR (500MHz, Chloroform-d) δ8.16(d, J=8.5Hz, 1H), 8.11(d, J=8.0Hz, 1H), 7.72(m, 1H), 7.60(d, J=8.0Hz ,2H),7.55(m,2H),7.53–7.50(m,3H),7.24(d,J=7.5Hz,2H),6.62(s,1H),3.87–3.76(m,4H),2.42( s,3H). 13C NMR (125MHz, DMSO) δ158.6, 154.9, 149.7, 146.6, 142.4, 139.6, 136.5, 135.1, 130.9, 129.7, 129.3, 129.0, 128.7, 128.0, 127.6, 126.6, 124.3, 121.3, 110.8, 2 ,21.0.HRMS(ESI):m / z calcd for(C 27 h 22 N 3 +H) + :388.1814; found: 388.1822.

Embodiment 3

[0050] Example 3 4-(4-chlorophenyl)-11-phenyl-1,2-dihydrobenzo[f]imidazo[2,1-α][2,7]quinoline

[0051]

[0052] The synthesis steps are the same as in Example 1, except that 2-(imidazolidine-2-ylidene)-1-phenylethane-1-one is replaced by 1-(4-chlorophenyl)-2-(imidazolidine-2 -ylidene)ethan-1-one to give a yellow solid.

[0053] Yellow solid, m.p.>250℃, 1 H NMR (500MHz, CDCl 3 )δ8.69(s,2H),8.15(m,2H),7.77(s,1H),7.62–7.48(m,8H),6.62(s,1H),3.80(s,4H). 13 C NMR (125MHz, CDCl 3 )δ156.9, 155.8, 150.4, 149.9, 149.3, 147.4, 143.0, 135.6, 131.1, 130.5, 130.0, 129.0, 127.9, 127.2, 127.1, 124.0, 123.4, 122.2, 111.5, 97.4: HR1.4, MS m / z calcd for (C 26 h 19 ClN 3 +H) + :408.1268; found: 408.1270.

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Abstract

The invention provides an imidazaphenanthridine compound as well as a preparation method and application thereof. Substituted 2-amino chalcone and amino ketene undergo a reaction to synthesize the imidazaphenanthridine compound under the room-temperature acidic condition. The preparation method provided by the invention has the advantages of mild reaction conditions, simple operation, no need of ametal catalyst, easily available raw materials, simultaneous introduction of a plurality of substituents and the like, and has a wide substrate application range. The imidazaphenanthridine compound prepared by the method has a certain optical property, can be used as a potential fluorescent molecule, and can be used as a fluorophore to be applied to fluorescence imaging. The structural general formula is shown in the specification.

Description

technical field [0001] The invention belongs to compound synthesis methods, and mainly relates to imidazophenanthridine compounds and their preparation methods and applications. Background technique [0002] The tricyclic planar group can be embedded between the stacking bases of DNA, and its planar group is perpendicular to the axis of the helix and interacts with the upper and lower bases through van der Waals force, causing the dye bound to DNA to show fluorescence, so the fluorescence based on phenanthridine Groups can be used for DNA detection. [0003] At present, the C-H bond activation strategy is mainly used to construct the phenanthridine core by metal-catalyzed synthesis (Chem-Eur.J.2013,19,10487-10491). [0004] [0005] The above methods require metal catalysis and have low yields and low substrate diversity. Therefore, it is necessary to provide a synthetic method with mild conditions and high reaction efficiency. Contents of the invention [0006] The ...

Claims

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Application Information

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IPC IPC(8): C07D471/14C09K11/06G01N21/64
CPCC07D471/14C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1059C09K2211/1088C09K2211/1092G01N21/643
Inventor 陈文腾应智敏柯迪罗峰刘双容邵加安俞永平
Owner ZHEJIANG UNIV
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