Bisindole alkaloid compound as well as synthesis method and application thereof
A technology of indole alkaloids and compounds, applied in the direction of active ingredients of heterocyclic compounds, organic chemical methods, drug combinations, etc., can solve many problems such as side effects, improper use, and inability to get rid of physical dependence and psychological dependence at the same time, and achieve inhibition The effect of cell proliferation
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Embodiment 1
[0053] Preparation of compound 1
[0054] 1. Preparation of Monomeric Alkaloid 1i
[0055]
[0056] first step:
[0057] At room temperature, 6-methoxyindole 1a was dissolved in anhydrous ether. After cooling down to 0°C, oxalyl chloride was added dropwise. After reacting for 3 hours, it was raised to room temperature and reacted for 1 hour to produce a red solid. Suction filter and wash with anhydrous ether solution. The filter cake was the crude compound 1b (yield 92%), which could be directly used in the next reaction without further purification.
[0058] Step two:
[0059] At room temperature, compound 1b was dissolved in absolute ethanol, and after cooling down to 0°C, triethylamine was added dropwise, and hydrogen chloride gas generated during the dropwise addition was taken away by argon flow. After the triethylamine was added dropwise, the reaction was heated under reflux for 3 hours. The temperature was lowered to 0°C, a yellow solid precipitated out, and it ...
Embodiment 2
[0108] Preparation of Compound 2
[0109] 1. Preparation of monomeric alkaloid 2d
[0110]
[0111] first step:
[0112] At room temperature, cesium carbonate was added into anhydrous acetonitrile, compound 2a and compound 2b were added, and the temperature was raised to 60°C. After reacting for 10 hours, it was cooled to room temperature, filtered through celite and washed with ethyl acetate. The organic phase was evaporated to dryness of solvent under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography to obtain compound 2c (yield 65%).
[0113] Step two:
[0114] Compound 2c was dissolved in nitrogen-nitrogen dimethylformamide at room temperature. Under the protection of argon, sodium formate, triphenylphosphine and palladium acetate were added, and the temperature was raised to 55°C for 6 hours. Water and dichloromethane were added, and the reaction solution was extracted 3 times with dichloromethane. The org...
Embodiment 3
[0141] Preparation of compound 3
[0142]
[0143] first step:
[0144] At room temperature, compound 3a and compound 3b were dissolved in 1% methanolic hydrochloric acid solution, and heated to reflux for 1 hour under the protection of argon atmosphere. Diluted with water, basified with sodium bicarbonate solution, extracted 3 times with dichloromethane. The organic phases were combined and washed with saturated sodium chloride solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography to obtain compound 3 (yield 68%).
[0145] Compound 3: 1 H NMR (600MHz, CD 3 OD) δ7.66(d, J=7.7Hz, 1H), 7.23(d, J=8.7Hz, 1H), 7.10(d, J=7.7Hz, 1H), 7.07(1H), 7.07(1H), 6.86(d, J=8.7Hz, 1H), 5.23(dd, J=12.4, 3.3Hz, 1H), 4.03(m, 1H), 3.99(s, 3H), 3.70(s, 3H), 3.52(d ,J=2.1Hz,1H),3.41(overlapped,2H),3.39(1H),3.21(1H),3.03(d...
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