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A kind of carbonitrile compound containing imidazole and 1,3,4-oxadiazole structure and its preparation method and application
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A technology containing imidazole and oxadiazole, which is applied in the field of nitrile compounds, can solve the problems of structure and biological activity that have not been reported in literature, and achieve the effect of good inhibitory activity, simple preparation method, and good anticancer activity
Active Publication Date: 2020-05-22
浙江工业大学上虞研究院有限公司
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[0003] The series 4-chloro-5-(p-methylphenyl)-1-(5-(substituted phenyl)-1,3,4-oxadiazol-2-yl)-1 designed and synthesized by the present invention H -imidazole-2-carbonitrile compounds, the structure and biological activity of which have not been reported in the literature
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Embodiment 1
[0022] The synthesis of embodiment 1 compound Ia (R=H)
[0023] 0.287 g (2.0 mmol) of 4-chloro-2-cyano-5-(p-methylphenyl)-1 H - Imidazole-1 carbohydrazide was added to 15 mL POCl 3 Add benzoic acid (2.2 mmol) to reflux reaction, and finally remove part of POCl by vacuum rotary evaporation 3 , 20 mL of ice water was added to the reaction bottle, stirred at room temperature for 3.5 h, a solid substance was precipitated, filtered, washed several times with water, and recrystallized with ethanol to obtain 0.527 g of yellow solid compound Ia, with a yield of 73.2%. m.p.: 104~106℃; 1 H NMR (500 MHz, CDCl 3 ) δ : 8.14(d, J = 7.0 Hz, 2H), 7.70 (d, J= 8.0 Hz, 2H), 7.62~7.50 (m, 4H), 7.29 (s,1H), 2.40 (s, 3H); HRMS (ESI), m / z calcd for C 19 h 13 ClN 5 O [M+H] + 362.0809; found, 362.0805.
Embodiment 2
[0024] The synthesis of embodiment 2 compound Ib (R=meta-methyl)
[0025] 0.287 g (2.0 mmol) of 4-chloro-2-cyano-5-(p-methylphenyl)-1 H -Imidazole-1 carbohydrazide was added to 10 mL POCl 3 In, add m-toluic acid 2.4 mmol again, reflux reaction. Finally, vacuum rotary evaporation removes part of POCl 3 , 20 mL of ice water was added to the reaction bottle, stirred at room temperature for 4.0 h, a solid substance was precipitated, filtered, washed several times with water, and recrystallized with n-hexane to obtain 0.481 g of yellow solid compound Ib, with a yield of 64.3%. m.p.: 120~124℃; 1 H NMR (500 MHz, CDCl 3 ) δ : 8.02 (s, 1H), 7.99 (d, J = 7.5 Hz, 1H), 7.72 (d, J = 8.0 Hz, 2H), 7.44~7.40 (m, 2H), 7.32 (d, J = 8.0 Hz, 2H), 2.46 (s, 3H), 2.43 (s, 3H) ; HRMS(ESI), m / z calcd for C 20 h 15 ClN 5 O [M+H] + 376.0965; found, 376.0959.
Embodiment 3
[0026] The synthesis of embodiment 3 compound Ic (R=p-methyl)
[0027] 0.287 g (2.0 mmol) of 4-chloro-2-cyano-5-(p-methylphenyl)-1 H -Imidazole-1 carbohydrazide was added to 13mL POCl 3 2.3 mmol of p-toluic acid was added, and the reaction was carried out under reflux. Finally, vacuum rotary evaporation removes part of POCl 3 , 20 mL of ice water was added to the reaction flask, stirred at room temperature for 3.0 h, solid matter precipitated out, filtered, washed several times with water, and recrystallized with ethyl acetate and petroleumether to obtain 0.480 g of yellow solid compound Ic, yield 63.9%. m.p.: 103~105℃; 1 H NMR (500MHz, CDCl 3 ) δ : 8.05 (d, J = 8.5 Hz, 2H), 7.70 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 7.30 (d, J = 8.0 Hz, 2H), 2.46 (s, 3H), 2.41 (s, 3H) ; HRMS(ESI), m / z calcd for C 20 h 15 ClN 5 O [M+H] + 376.0965; found, 376.0957.
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Abstract
The invention discloses a carbonitrile compound containing imidazole and a 1,3,4-oxadiazole structure, and a preparation method and an application thereof. The preparation method of the carbonitrile compound containing imidazole and the 1,3,4-oxadiazole structure comprises the following steps: carrying out a cyclization reaction on 4-chloro-2-cyano-5-(p-methylphenyl)-1H-imidazole-1-carbohydrazideand substituted benzoic acid in phosphorus oxychloride under a refluxing condition, and separating and purifying the above obtained reaction solution after the reaction ends in order to prepare the carbonitrile compound containing imidazole and the 1,3,4-oxadiazole structure. The preparation method has the advantages of simplicity and convenience in post-treatment, the obtained compound has good anticancer activity, and anticancer activity determination of the prepared compound on human livercancer cells, human lungcancer cells A549 and human coloncancer cells HCT116 is performed through adopting tetrazole rapid colorimetry. A bioassay result shows that the compound has certain inhibitory activity on all the tested targets; and the inhibitory activity of most of the compounds on the human coloncancer cell line HCT116 and a human hepatoma cell line Huh7 is higher than the inhibitory activity on the human lungcancer cell line A549.
Description
technical field [0001] The present invention relates to cyanonitrile compound containing imidazole and 1,3,4-oxadiazole structure and its preparation method and application, specifically 4-chloro-5-(p-methylphenyl)-1-(5-( Substituted phenyl)-1,3,4-oxadiazol-2-yl)-1 H -Imidazole-2-carbonitrile compounds and their preparation methods and applications. Background technique [0002] Imidazole structural compounds have a wide range of biological activities, such as antitumor (Journal of Medicinal Chemistry., 2002, 45(8): 1697-1711), anti-inflammatory (WO 03030902. 2003-04-17), antibacterial ( Bioorganic & Medicinal Chemistry Letters., 1999, 30(32): 1023-1028), anticancer (European Journal of Medicinal Chemistry., 2010, 45(7): 2949-2956), antidepressant (Iranian Journal of Pharmaceutical Research. , 2008, 7(1): 29-33) and other activities; in the field of pesticides, it is often used as fungicide (European Journal of Organic Chemistry., 2017, (3): 695-703), insecticide (Pesticid...
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