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A kind of α-Lappaol analog and its synthetic method and application as antitumor drug
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A synthesis method and analog technology are applied in the fields of antitumor drugs, drug combinations, organic chemistry, etc., to achieve the effects of easy availability of raw materials, high yield and simple operation.
Active Publication Date: 2017-12-26
XINXIANG MEDICAL UNIV
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[0004] The innovation of the present invention lies in the synthesis of an α-lapachol containing an indole structure. This compound has not been reported yet. According to the preliminary pharmacological activity determination, this compound has strong anti-tumor activity
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Embodiment 1
[0018] 1.93 g of 2-phenylindole, 1.51 g of p-nitrobenzaldehyde, 1.74 g of 2-hydroxyl-1,4-naphthoquinone and 0.22 g of indium trichloride were placed in a 50 ml reaction flask and mixed evenly, heated and stirred, The temperature was controlled at 100°C, and after 1.5 hours of reaction. The reaction mixture was dissolved with 30 ml of dichloromethane, washed twice with 20 ml of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with ethanol to obtain 3.51 g of the orange-yellow target compound with a yield of 71%. 1 H NMR ( 400 MHz , DMSO- d 6) δ : 11 .48 ( s, 1H), 11.15 ( s, 1H ), 8.09 (d, 2H, J = 8 4 Hz), 7.95 (d, 1H, J = 6.8Hz, 7.86 (d, 1H , J = 6.8 Hz ), 7 .77 ( t, 1H, J = 7 .6 Hz ), 7.46-7.28(m, 10H ),7.06 ( t, 1H, J = 7.2 Hz ), 6.85 ( t, 1H, J = 7.2 Hz ), 6 .20 (s,1H); 13 C NMR ( 100MHz, DMSO- d 6) δ : 184.2, 181.7, 152.3, 146.0, 137.6,136.6, 135.2,133.6, 132.4, 130.2, 129.7, 129.8, 128.2, 127.9,126.0, 123.5,...
Embodiment 2
[0020] Put 9.65 g of 2-phenylindole, 16.6 g of p-nitrobenzaldehyde, 8.70 g of 2-hydroxy-1,4-naphthoquinone and 1.10 g of indium trichloride in a 100 ml reaction flask and mix well, heat and stir , the temperature was controlled at 110°C, and after 2 hours of reaction. The reaction mixture was dissolved in 100 ml of dichloromethane, washed twice with 100 ml of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized from ethanol to obtain 32.5 g of the orange-yellow target compound with a yield of 65%.
Embodiment 3
[0022] Put 19.3 g of 2-phenylindole, 18.1 g of p-nitrobenzaldehyde, 17.4 g of 2-hydroxy-1, 4-naphthoquinone and 2.2 g of indium trichloride in a 250 ml reaction flask and mix evenly, heat and stir , the temperature was controlled at 120°C, and after 2.5 hours of reaction. The reaction mixture was dissolved in 200 ml of dichloromethane, washed twice with 200 ml of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with ethanol to obtain 3.04 g of the orange-yellow target compound with a yield of 62%.
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Abstract
The invention provides an α-lapachol analog and a synthesis method thereof. The method adopts uniformly mixing 2-phenylindole, 2-nitrobenzaldehyde, 2-hydroxy-1,4-naphthoquinone and indium trichloride with a catalyst amount, heating and stirring, and controlling the temperature at 100-120° C. Reaction 1.5‑2.5 hours. The introduction of nitro and indole structures into the α-lapacol analog of the present invention makes it more active and easier to absorb, and has obvious inhibitory effect on different tumor cell lines. The method of the invention has the characteristics of environmental protection, easy-to-obtain raw materials, simple operation and high yield.
Description
technical field [0001] The present invention relates to a kind of α-lapachol analogue, specifically, relate to a kind of 2-hydroxyl-3-((4-nitrophenyl)(2-phenyl-1 H -indol-3-yl)methyl)naphthalene-1,4-dione, including the preparation method of this compound and its use as a medicine for the preparation of malignant tumors. Background technique [0002] Malignant tumor is one of the important diseases that endanger human health at present. It is the first killer of human beings in the new century and poses the most serious threat to human survival. The development and research of new and effective anti-tumor drugs is a major topic and long-term task in the field of biomedical research. . α-Lappaol, chemical name 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone, was originally isolated from the natural product Tabebuia avellanedae from Central and South America Yes, α-lapachol has a wide range of biological activities, including antifungal, antiviral, anti-inflammatory, ant...
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