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A class of β-carboline cyanofuran derivatives and its preparation method and application
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A technology of carboline cyanofuran and derivatives, applied in the field of β-carboline cyanofuran derivatives and its preparation, can solve the problems of shallow volume, low fluorescence quantum yield of photosensitizers, and limited depth of tissue penetration , to achieve broad application prospects, low dark toxicity, and high stability
Active Publication Date: 2021-09-28
NANTONG UNIVERSITY
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Although traditional fluorescent dyes are not therapeutic agents, the fluorescencequantum yield of most photosensitizers is also much lower than that of traditional fluorescent dyes
At the same time, the short-wavelength excitation of photosensitizers significantly limits the depth of their tissue penetration, so the volumes probed under these conditions are relatively shallow
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Embodiment 1
[0042] Example 1: (E)-methyl 1-(2-(4-cyano-5-(dicyanomethylene)-2,2-dimethyl-2,5-dihydrofuran-3- Base) vinyl)-9H-pyridin[3,4-b]indole-3-carboxylic acid methyl ester (I 1 ) preparation;
[0043] Add 1-formyl-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester (254mg, 1.0mmol) and 5ml absolute ethanol in eggplant-shaped single-necked bottle, then add 2-(3 -cyano-4,5,5-trimethylfuran-2(5H)-methylene)malononitrile (219mg, 1.1mmol), then add a catalytic amount of ammonium acetate (7.7mg, 0.1mmol), reflux Stir overnight. After the completion of the reaction as monitored by TLC, suction filtration was performed, the filter cake was rinsed with cold ethanol several times, the filter cake was vacuum-dried, and recrystallized again to obtain 318 mg of a yellow solid product. Yield 73.1%. (I 1 ) spectrum data is: ESI-MS (m / z): 436[M+H] + ; 1 H NMR (d 6 -DMSO, 400MHz): δ12.69(s, 1H, NH), 9.03(s, 1H, Ar-H), 8.49(d, J=7.8Hz, 1H, Ar-H), 8.27(d, J= 15.8Hz,1H,CH),8.04–7.94(m,1H,Ar-H...
Embodiment 2
[0044] Example 2: (E)-2-(3-cyano-4-(2-(3-(hydroxymethyl)-9-methyl-9H-pyrido[3,4-b]indole-1 -yl)vinyl)-5,5-dimethylfuran-2(5H)-methylene)malononitrile (I 2 ) preparation;
[0045] With reference to (I in embodiment 1 1 ) synthetic method, the 1-formyl-9H-pyrido in the method is replaced by 3-(hydroxymethyl)-9-methyl-9H-pyrido[3,4-b]indole-1-formyl [3,4-b]Methyl indole-3-carboxylate, and finally a yellow solid (I 2 ) 289 mg, the yield was 68.6%. (I 2 ) spectrum data is: ESI-MS (m / z): 422[M+H] + ; 1 H NMR (d 6 -DMSO,400MHz):δ9.01(s,1H,Ar-H),8.43(d,J=7.2Hz,1H,Ar-H),8.22(d,J=15.8Hz,1H,CH),8.00 –7.92(m,1H,Ar-H),7.71–7.63(m,2H,Ar-H,CH),7.35–7.29(m,1H,Ar-H),4.98–4.94(m,1H,OH) ,4.21–4.17(m,2H,CH 2 ),3.82(s,3H,CH 3 ), 2.02(s,6H,CH 3 ).
Embodiment 3
[0046] Example 3: (E)-2-(3-cyano-4-(2-(1,9-dimethyl-9H-pyridin[3,4-b]indol-3-yl)ethenyl) -5,5-Dimethylfuran-2(5H)-methylene)malononitrile (Ⅱ 1 ) preparation;
[0047] With reference to (I in embodiment 1 1 ) synthetic method, 1-formyl-9H-pyrido[3,4- b] methyl indole-3-carboxylate, and finally a red solid (Ⅱ 1 ) 290 mg, the yield was 71.6%. (II 1 ) spectrum data is: ESI-MS (m / z): 406[M+H] + ; 1 HNMR(d 6 -DMSO, 400MHz): δ8.19(d, J=7.2Hz, 1H, Ar-H), 7.83(d, J=15.8Hz, 1H, CH), 7.59–7.55(m, 2H, Ar-H, CH),7.46–7.42(m,2H,Ar-H),7.37–7.33(m,1H,Ar-H),3.91(s,3H,CH 3 ),3.10(s,3H,CH 3 ),1.93(s,6H,CH 3 ).
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Abstract
The present invention relates to the technical field of biomedicine, in particular to a class of β-carboline cyanofuran derivatives and their preparation method and application, having the structure shown in general formula I or II: the present invention combines a large class of naturally occurring indoles Alkaloids, the structure of β-carboline derivatives has a planar tricyclic structure skeleton of pyrido [3,4-b] indole; the 1-position or 3-position of the β-carboline parent ring is introduced by Knoevenagel condensation reaction The five-membered ring cyanofuran segment with strong electron-withdrawing properties further prolongs the conjugated system of β-carboline. Using the ICT effect, two types of β-carboline cyanofuran with photodynamic effect and pH-sensitive fluorescence were designed and obtained. derivative. This type of compound has the characteristics of high stability and low dark toxicity. At the same time, it can generate highly active singlet oxygen under laserirradiation, which can effectively eliminate tumors. It provides an effective tool for medical monitoring and treatment of tumors. It has good application prospects in imaging, treatment, monitoring and so on.
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