Use of a class of dehydroabietic acid indole derivatives
A technology of indole derivatives and dehydroabietic acid is applied in the application field of anti-tumor to achieve the effects of good anti-tumor effect and strong cytotoxic activity
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Embodiment 1
[0022] The synthesis of embodiment 1 dehydroabietic acid methyl ester (III)
[0023] In a 500mL three-necked round bottom flask, 30g (0.1mol) of dehydroabietic acid was dissolved in 100mL of benzene, and 10.9mL of thionyl chloride (17.85g, 0.15mol) was slowly added, and heated to reflux for 3h. After the reaction, benzene and excess thionyl chloride were distilled off to obtain yellow oily dehydroabietoyl chloride. Add 60mL of methanol to the bottle and heat to reflux for 2h. After the reaction, the solvent was distilled off, and the product was recrystallized from ethanol to obtain methyl dehydroabietate (28.9 g, 92%) in the form of white needles.
[0024] m.p.62.3-63.9℃,IR(KBr,cm -1 ):ν3052,2994,2930,2868,1721,1381,1250,1082,825. 1 HNMR (CDCl 3 ,300MHz):δ1.23(d,J=7.1Hz,6H,13-CH(CH 3 ) 2 ),1.27(s,3H,CH 3 ),1.42(m,1H),1.50(m,1H),1.57(s,3H,CH 3 ),1.61-1.70(m,5H),2.24(dd,J=12.5,2.1Hz,1H),2.30(d,J=12.3Hz,1H),2.80-2.90(m,3H),3.66(s, 3H, COOCH 3 ),6.88(d,J=1.5Hz,1H,H-14),...
Embodiment 27
[0025] The synthesis of embodiment 27-carbonyl dehydroabietic acid methyl ester (IV)
[0026] Methyl dehydroabietate (8 g, 25.5 mmol) was dissolved in 30 mL of glacial acetic acid, and chromium trioxide (2.64 g, 26.4 mmol) was dissolved in 18 mL of acetic acid / acetic anhydride (1:2, v / v). Then, the chromium trioxide solution was slowly added dropwise to the methyl dehydroabietate solution at 0° C. with stirring, and the reaction solution was stirred overnight at room temperature. After the reaction, the reaction solution was poured into ice water, extracted three times with dichloromethane, the organic phases were combined, washed with saturated sodium bicarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The product was purified by silica gel column chromatography (petroleum ether / acetone 100:1, v / v) to obtain methyl 7-oxo-dehydroabietic acid (5.36 g, 64%) as a yellow oil.
[0027]...
Embodiment 3
[0028] The synthesis of embodiment 3 dehydroabietic acid indole derivatives (V)
[0029] 1.8 g (5.5 mmol) of compound IV was dissolved in 20 mL of ethanol, 1.74 g (12 mmol) of phenylhydrazine hydrochloride and 2 mL of concentrated hydrochloric acid were added, and the reaction mixture was heated to reflux for 3 h. After the reaction, the mixture was poured into ice water, extracted three times with dichloromethane, the organic phases were combined, washed with saturated sodium bicarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The product was purified by silica gel column chromatography (petroleum ether / acetone 50:1, v / v) to obtain compound V as a white powder (1.35 g, 61%).
[0030] Mp170-172℃; IR(KBr,ν,cm -1 ):3370,2958,2930,2868,1700,1460,1441,1263. 1 HNMR (CDCl 3):1.10(s,3H,H-14),1.31(d,3H,J=7Hz,H-17orH-18),1.32(d,3H,J=7Hz,H-18orH-17),1.69(m ,1H),1.77(s,3H,H-15),1.80-2.00(...
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