A kind of 1,2,3,4-tetrahydroacridine-9-amine compound and its preparation method and use
The technology of an amine compound and tetrahydroacridine, which is applied in the field of medicine, can solve the problems of single drug target and inability to adapt to the pathological environment, and achieve the effect of simple preparation method, easy-to-obtain raw materials, and weaken the neurotoxicity of Aβ
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specific Embodiment 1
[0048] A novel 1,2,3,4-tetrahydroacridin-9-amine compound, the compound is a compound with the structural formula shown in formula I and II, or a pharmaceutically Acceptable salts, esters or solvates,
[0049]
[0050] Among them, R 1 for H, CH 3 , OCH 3 , OCH 2 CH 3 , Cl, Br, CF 3 , NO 2 , NH 2 Or straight-chain alkanes with carbon number 1-5, R 2 , R 3 for H, n=1, 2, 3, 4 or 5, m=1, 2, 3, 4 or 5, the pharmaceutically acceptable salt, ester or solvate of the compound described in the above formula I and II, wherein the salt is an inorganic acid Salts or organic acid salts; inorganic acid salts are selected from the salts formed by any of the following inorganic acids: hydrochloric acid, sulfuric acid and phosphoric acid; organic acids are selected from the salts formed by any of the following organic acids: acetic acid, trifluoroacetic acid, propane Diacids, citric acid and terephthalic acid.
[0051] The novel 1,2,3,4-tetrahydroacridin-9-amine compounds r...
specific Embodiment 2
[0054] The specific embodiment above is a preparation method of a novel 1,2,3,4-tetrahydroacridin-9-amine compound, comprising the following steps:
[0055] (1) react the compound of formula III and sodium hydroxide in methanol aqueous solution to obtain the compound of formula IV; specifically, at 40°C, dissolve the compound of formula III and sodium hydroxide in an equal volume ratio of 1:1.3 molar ratio React in the mixed aqueous methanol solution for 6 hours to obtain the compound shown in formula IV; thus, it is beneficial to improve the reaction efficiency, reduce side reactions, and increase the yield;
[0056] (2) react the compound of formula IV and the compound of formula V in phosphorus oxychloride to obtain the compound of formula VI; specifically, at 0°C, add the compound shown in formula IV and the compound shown in formula V according to the molar ratio of 1:1.2 In phosphorus oxychloride, transfer to 110 DEG C and react for 6 hours to obtain the compound shown i...
Embodiment 1
[0064] Example 1: Compound 1 preparation of
[0065] 1. Preparation of 2-aminobenzoic acid
[0066] Ethyl 2-aminobenzoate (6.06 mmol) and sodium hydroxide (7.878 mmol) were stirred in methanol (5 mL) and water (5 mL), and the mixture was stirred at 40° C. for 6 hr. After the reaction was completed, methanol was removed by rotary evaporation, and the resulting solution was acidified to pH 3-4 with hydrochloric acid. The resulting suspension was stirred for 10 minutes, the precipitate was filtered and dried to obtain a white solid powder with a yield of 95%. The structural data of the compound was characterized as: 1 H NMR (600MHz, CDCl 3 ):7.69(d, J=7.8,1H),6.93(t,J=7.6,1H),6.45(d,J=8.1,1H),6.37(t,J=6.4,1H),3.17(s, 1H).
[0067] 2. Preparation of 9-chloro-1,2,3,4-tetrahydroacridine
[0068] The intermediate 2-aminobenzoic acid (3.6 mmol) and cyclohexanone (4.32 mmol) obtained in the previous step were added into phosphorus oxychloride (10 mL) at 0°C, and then refluxe...
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