Alpha-mangostin derivatives and their applications
A technology of drugs and compounds, applied in the field of medicine
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Embodiment 1
[0061] Example 1. Preparation of compounds 2b-2c, 3a-3g.
[0062] Synthesis of Intermediate 1: α-Mangostin (5.0 g, 12.18 mmol) was dissolved in dry benzene (80 mL) followed by addition of dichlorodicyanobenzoquinone (DDQ) (3.0, 13.39 mmol). The reaction solution was heated to 80°C and refluxed for 3h. After the reaction was completed, filter while hot and evaporate the solvent in the filtrate to dryness. The obtained crude product was subjected to silica gel column chromatography (V 乙酸乙酯 : V 石油醚 =3:20) and purified to obtain yellow solid 1 (4.1 g, 10.04 mmol, yield 82%).
[0063] Compound: 5,9-Dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-2H,-6H-pyrano[ 3,2-B]xanthene-6-one 5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-2H,6H-pyrano[ 3,2-B]xanthen-6-one(1). Yield: 82%. 1 H NMR (400MHz, CDCl 3 )δ13.69(s, 1H), 6.82(s, 1H), 6.72(d, J=10.2Hz, 1H), 6.35(s, 1H), 6.24(s, 1H), 5.56(d, J=10.0 Hz,1H),5.31-5.21(m,1H),4.08(d,J=6.3Hz,2H),3.80(s,3H),1.83...
Embodiment 2
[0085] Example 2. Preparation of compounds 4a-4g.
[0086] Synthesis of compound 4a: Hydroxylamine hydrochloride (31 mg, 0.44 mmol) and sodium hydroxide (44 mg, 1.10 mmol) were dissolved in dry acetone (3 mL). After the reaction solution was stirred at room temperature for 10 minutes, 3a (110 mg, 0.22 mmol) was added and heated to 50° C. and refluxed for 6 h. After the reaction was completed, 10 ml of 5% dilute sulfuric acid was added and extracted three times with an equal volume of ethyl acetate. The organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was evaporated to dryness, and the obtained crude product was subjected to silica gel column chromatography (V 甲醇 : V 二氯甲烷 =1:99) was purified to obtain yellow solid 4a (60.5 mg, 0.13 mmol, yield 59%).
[0087] Synthesis of compound 4b: Hydroxylamine hydrochloride (32 mg, 0.46 mmol) and sodium hydroxide (46 mg, 1.15 mmol) were dissolved in dry acetone (5 mL). After the reaction solution ...
Embodiment 3
[0101] Example 3. Preparation of Compound 5.
[0102] Synthesis of compound 5: 2b (56.4 mg, 0.10 mmol) and potassium carbonate (166 mg, 1.20 mmol) were dissolved in dry acetone (5 mL), followed by the addition of pyrrolidine (0.1 ml, 1.21 mmol). The reaction solution was heated to 50°C and refluxed overnight. After the reaction, 10 ml of water was added and extracted three times with an equal volume of ethyl acetate. The organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was evaporated to dryness, and the obtained crude product was subjected to silica gel column chromatography (V 甲醇 : V 二氯甲烷 =3:97) was purified to obtain yellow solid 5 (40 mg, 0.07 mmol, 71% yield).
[0103] Compound: 5-Hydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-9-((6-(pyrrolidine-1- yl)hexyl)oxy)-2H,-6H-pyrano[3,2-b]xanthene-6-one (5-hydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut -2-en-1-yl)-9-((6-(pyrrolidin-1-yl)hexyl)oxy)-2H,6H-pyrano[3,2-b]xanthen-6-...
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