Novel triptolide derivatives for treating autoimmune diseases
A technology of autoimmunity and compounds, which is applied in the preparation of new intermediates of various compounds and compounds to treat patients with autoimmune diseases, and can solve problems such as limited toxicity and narrow therapeutic index
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Embodiment 1
[0061] Example 1 Preparation of [5aS-(5aα, 5bα, 8β, 9α, 9aR * , 10aβ)]-4,5a,5b,8,9,10a,11,11a-octahydro-5b,8,9-trihydroxy-5a-methyl-8-(1-methylethyl)-1H - Oxivino[8a,9]phenanthrene[1,2-c]furan-3(5H)-one Preparation of intermediate [1bS-(1aR * , 1bα, 6bβ, 7aβ, 8aR * , 9α, 10β, 11α, 11aβ)]-11-bromo-1b, 3,6,6b,7,7a,9,10,11,11a-decahydroxy-10-(1-methylethyl)-1b -Methyl-dioxirano[4b,5:8a,9]phenanthrene[1,2-c]furan-4(2H)-one
[0062] Synthetic Route A, Step A: Triptolide (100 mg, 277 μmol, optically active, isolated from a natural source) was mixed with acetone (30 mL), water (2.5 mL) and 30% aqueous HBr (800 μL), and the reaction mixture Heat at 70°C for 70 minutes. The reaction mixture was then poured into water (60 mL) and concentrated in vacuo. The residual phase was extracted with dichloromethane (3 x 60 mL) and the combined organic extracts were washed with brine (60 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in va...
Embodiment 2
[0064] Example 2 Preparation of [5aR-(5aα, 6α, 7β, 9aα, 9bα)]-3b, 4, 5, 5a, 6, 7, 9a, 9b, 10, 11-decahydro-5a, 6, 7, 9a -Tetrahydroxy-9b-methyl-7-(1-methylethyl)-phenanthrene[1,2-c]furan-1(3H)-one Preparation of intermediate [5aR-(5aα, 6α, 6aα, 7aα, 7bβ, 8aS * ,8bα)]-3,3b,4,5,5a,6,6a,7a,7b,8b,9,10-dodecahydro-5a,6-dihydroxy-6a-(1-methylethyl) -8b-methyl-1H-dioxirano[4b,5:6,7]phenanthrene[1,2-c]furan-1-one
[0065] Scheme A, Step C: To a stirred solution of triptolide (360 mg, 1 mmol, optically active, isolated from natural source) in anhydrous THF (10 mL) was added sodium cyanoborohydride (360 mg, 6 mmol), followed by the dropwise addition of pure boron trifluoride diethyl ether (150 μL). The resulting solution was stirred at room temperature for 16 hours. The reaction was then quenched by the addition of 1N aqueous ammonium chloride (25 mL) and extracted with diethyl ether (3 x 25 mL). The combined organic extracts were washed with brine (25 ...
Embodiment 3
[0070] Example 3 Preparation of [5R-(5α, 5aβ, 6β, 7α, 9aβ, 9bβ)]-3b, 4, 5, 5a, 6, 7, 9a, 10, 11-decahydro-5a, 6, 9a-three Hydroxy-9b-methyl-7-(1-methylethyl)-5,7-epoxyphenanthrene[1,2-c]furan-1(3H)-one
[0071] Synthetic route B, step A: Triptolide (48 mg, 0.133 μmol, optically active, isolated from natural source) was dissolved in acetonitrile (2 mL) at room temperature under nitrogen, and the solution was added dropwise to triphenyl In a stirred mixture of phosphine (40 mg, 0.153 mmol) and iodine (21.2 mg, 0.084 mmol) in acetonitrile (3 mL). The reaction mixture was stirred at room temperature for 10 minutes, then at 75°C for 2 hours. Acetonitrile was removed in vacuo, and water (20 mL) was added. The aqueous suspension was extracted with ethyl acetate (3 x 20 mL), the combined organic extracts were washed with 10% aqueous sodium bisulfite (20 mL), brine (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give ...
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