S-indole benzamide derivative as well as preparation method and application thereof
A technology of indole benzamide and derivatives, applied in organic chemistry, antiviral agents, etc., can solve the problems of indole derivatives with insufficient antiviral activity, limitations, and complex synthesis processes
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Embodiment 1
[0031] Preparation of compound 1:
[0032]
[0033] Add 7g (60mmol) of indole and 300mL of dry diethyl ether into a reaction flask, add 16.1mL of oxalyl chloride dropwise to the reaction solution at 0°C, after the drop is complete, react at room temperature for 6h, and a yellow suspension is formed. Placed at 0°C again, 12 mL of methanol was added dropwise thereto, stirred for 30 min, the resulting mixture was filtered and washed with glacial ether, and finally 10.93 g of yellow solid 1 was obtained, with a yield of 90%.
[0034] Preparation of compound 2:
[0035]
[0036] In a three-necked flask, under nitrogen protection, inject 47mL of lithium aluminum hydride (4.44g, 117mmol, 2.5mol / L THF solution), place at 0°C, and dissolve 10.15g (50mmol) of yellow solid 1 in 36mL of THF , added dropwise to the above solution for 1 hour, then heated to 70°C to keep the reaction for 4 hours, the reaction was complete, and the Fieser treatment was used to quench the reaction, the ...
Embodiment 2
[0053] Safety performance test
[0054] The S-indolebenzamide derivative 6i prepared in Example 1 was used for the acute toxicity test on mice, and the steps and effects were as follows:
[0055] (1) Get 60 BALB / c mice, half male and half female, each weighing about 18-20g, 10 mice in each group, and randomly divide them into 6 groups, namely blank control group and 5 drug administration groups (medication group Doses were 8000, 4000, 2000, 1000 and 500 mg / kg body weight, respectively). Fasting (drinking water) for 6 hours before and after the administration, the dosage of the test group was calculated according to the body weight of each mouse, the total volume was 0.4 mL each, and the metal gavage device was used for one-time gavage administration. The mice in the control group maintained free access to food and water.
[0056] (2) Results: After observing the 500mg / kg weight group mice, no abnormal reaction was found, and their skin, stool, breathing, limb activities, beh...
Embodiment 3
[0062] The S-indolebenzamide derivative 6i prepared in Example 1 is tested for inhibition of influenza virus, the steps of use and the effect are as follows:
[0063] (1) Half lethal dose LD for mice of H1N1 influenza virus GX6 strain 50 Determination of
[0064] The experiment was divided into 7 groups, with 8 female BALB / c mice in each group, aged 6-8 weeks, weighing 18-20g. The cytotoxicity with a stable titer of 26 was used as the original toxin, and the original toxin was diluted 10 times to 10 -5 Inoculated BALB / c mice. At the same time set up a control group.
[0065] Before inoculation, the mice were treated with dry ice, and after the mice fainted, the method of intranasal drip was used to group them according to different viruses, and each mouse was given 50 μL of virus. After taking the poison, record the body weight change and death every day. After recording and observing for 14 days, calculate the LD according to the Reed&Muench me...
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