Dual aryl tertiary amine azole compounds with biological activity as well as preparation method and medical application thereof
A kind of azole compound and compound technology, applied in the medical application of novel bisaryl tertiary amine azole compound, novel bis aryl tertiary amine azole compound and its pharmaceutically acceptable salt, achieving low cost and easy raw material The effect of obtaining and synthesizing is simple
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Embodiment 1
[0047] Example 1: Preparation of 2-chloro-N-(2-chloroethyl)-N-((4-chlorophenyl)(phenyl)methyl)ethylamine (compound 1 for short):
[0048]
[0049] Taking 4-chlorobenzophenone as the starting material, the intermediate 1-chloro-4-(chloro(phenyl)methyl)benzene is obtained through sodium borohydride reduction and thionyl chloride chlorination, and the intermediate is then subjected to Alkylation of diethanolamine nitrogen and chlorination of thionyl chloride to obtain the compound 1 It is a yellow liquid, and the total yield of the four-step reaction is 16.2%.
Embodiment 2
[0050] Example 2: N-(2-(1 H Preparation of -1,2,4-triazol-1-yl)ethyl)-2-chloro-N-((4-chlorophenyl)(phenylmethyl)ethylamine (compound 2 for short):
[0051]
[0052] Add 5 mL of acetonitrile, 0.18 g (1.32 mmol) of anhydrous potassium carbonate and 0.048 g (0.70 mmol) of 1,2,4-triazole into a 50 mL single-necked round bottom flask, react at 50 °C for 1 h, and cool to room temperature , 0.20 g (0.59 mmol) of 2-chloro-N-(2-chloroethyl)-N-((4-chlorophenyl)(phenyl)methyl)ethylamine was added under stirring. TLC detects to the end of the reaction, extracts by distillation under reduced pressure, concentrates, and obtains the compound by column chromatography 2 It is 0.063 g of yellow liquid, and the yield is 28.6%. IR (KBr) n: 3122 (Ar-H), 2945, 2832 (CH 2 ), 1543, 1507, 1490 (aryl skeleton, C=C), 1362, 1222 (C-N), 1091, 840, 770, 704 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ: 8.06 (s, 1H, triazole 5-H), 7.93 (s, 1H, triazole 3-H), 7.31 (q, 3H, J = 5.6 Hz, Ar H), 7.20 (q, 6...
Embodiment 3
[0053] Example 3: N-(2-(1H-imidazol-1-yl)ethyl)-2-chloro-N-((4-chlorophenyl)(phenyl)methyl)ethylamine (compound 3 for short) Preparation of:
[0054]
[0055] Add 10 mL of freshly evaporated tetrahydrofuran, 0.038 g (1.60 mmol) of NaH (1.60 mmol), and 0.095 g (1.40 mmol) of imidazole into a 50 mL three-neck round bottom flask, react at 50 °C for 1 h, cool to room temperature, and add 2-chloro- N-(2-Chloroethyl)-N-((4-chlorophenyl)(phenyl)methyl)ethylamine 0.40 g (1.17 mmol). TLC detects that until the reaction is completed, the solvent is evaporated under reduced pressure, extracted, dried over anhydrous sodium sulfate, and the compound is obtained by column chromatography 3 It is 0.096 g of colorless liquid, and the yield is 21.9%. 1 H NMR (300 MHz, CDCl 3 ) δ: 7.40 (s, 1H, imidazole 2-H), 7.26 ~ 7.15 (m, 9H, Ar H), 7.04 (s, 1H, imidazole 5-H), 6.76 (s, 1H, imidazole 4-H) , 4.83 (s, 1H, CH), 3.90 (s, 2H, imidazole CH 2 ), 3.36 (s, 2H, ClCH 2 ), 2.92 (d, J = 6.1 H...
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