6-position derivatives of phenanthrene and indolizidine alkaloids and their preparation, anti-plant virus and anti-cancer activities
A technology for phenanthroindolizidine and alkaloids, which is applied to the 6-position derivatives of phenanthroindolizidine alkaloids and the fields of their preparation, anti-plant virus and anti-cancer activities, and can solve the problem of 6-position substituents. The lack of reports on the application of anti-cancer activity, the lack of reports on the effect of the 6-position substituent activity, and the unfavorable practical application, etc., achieve the effects of excellent anti-plant virus activity, high in vitro anti-TMV activity, and good in vivo activity
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Embodiment 1
[0026] Embodiment 1: phenanthrene and indolizidine alkaloid 6-position carboxylic acid derivative (I a )Synthesis
[0027]
[0028] Compound (R / S)-6-O-desmethylantorphine was dissolved in anhydrous dichloromethane, EDCI, TEA, different acids and DMAP were added respectively, and reacted at room temperature for 10 h. After the reaction was detected by TLC, saturated ammonium chloride was added, separated, the organic phase was washed with saturated NaCl, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain compound Ia.
[0029] Compound I a -1
[0030] Yield: 80%. Pale yellow solid. Melting point: 218-219°C. 1 H NMR (400MHz, CDCl 3)δ8.16(d, J=2.4Hz, 1H), 7.89-7.87(m, 2H), 7.30-7.27(m, 2H), 4.69(d, J=14.8Hz, 1H), 4.13(s, 3H ), 4.08(s, 3H), 3.69(d, J=14.8Hz, 1H), 3.51-3.46(m, 1H), 3.34(dd, J=16.0Hz, 2.4Hz, 1H), 2.93-2.87(m , 1H), 2.71-2.65(m, 1H), 2.48-2.42(m, 2H), 2.29-2.18(m, 3H), 2.10-2.00(m, 1H), 1.97-1.88(m, 3H), 1.82 -1.66(m, 4H),...
Embodiment 2
[0071] Embodiment 2: the phenanthrene and indolizidine alkaloid derivative (I b )Synthesis
[0072]
[0073] Dissolve 6-O-(2-hydroxyethyl) desmethylantorphine in anhydrous dichloromethane, add EDCI (2equiv), TEA (2equiv), Boc protected amino acid (lequiv) and DMAP (0.2equiv ), react at room temperature for 10h. After the reaction was detected by TLC, saturated ammonium chloride was added, separated, the organic phase was washed with saturated NaCl, dried over anhydrous sodium sulfate, and separated by column chromatography (CH 2 Cl 2 :MeOH=40:1) to obtain the compound, the compound was dissolved in dichloromethane (20mL), TFA (20equiv) was added dropwise, reacted at room temperature for 1h, and the reaction solution was poured into saturated NaHCO 3 middle, liquid separation, the aqueous phase was extracted with dichloromethane, the organic phases were combined, washed with NaCl, dried over anhydrous sodium sulfate, and spin-dried to obtain compound I b .
[0074] Comp...
Embodiment 3
[0094] Embodiment 3: the assay of anti-tobacco mosaic virus activity, assay procedure is as follows:
[0095] 1. Virus purification and concentration determination:
[0096] Virus purification and concentration determination were carried out in accordance with the SOP specification for tobacco mosaic virus compiled by the Bioassay Laboratory of the Institute of Elements, Nankai University. After the crude virus extract was centrifuged twice with polyethylene glycol, the concentration was measured and refrigerated at 4°C for later use.
[0097] 2. Compound solution preparation:
[0098] After weighing, the original drug was dissolved in DMF to prepare 1×10 5 μg / mL mother solution, and then diluted with 1‰ Tween 80 aqueous solution to the required concentration; Ningnanmycin preparation was directly diluted with water.
[0099] 3. In vitro effect:
[0100] Rub inoculation of leaves of Shanxi tobacco at the right age, rinse with running water, the virus concentration is 10 μg...
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