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Phenanthroindolizidine alkaloid glycosylation product, 6-site derivatization product, and preparation methods and plant virus resistance activities of phenanthroindolizidine alkaloid glycosylation product and 6-site derivatization product

A technology of phenanthroindolizidine and indolizidine, applied in the field of anti-plant virus activity, can solve the problems that the 6-position substituent has not been studied, and the method of 6-position derivatization is lack of reports.

Active Publication Date: 2014-07-16
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Both (R)-Antorfen and (R)-6-O-desmethyl Antorfen have good anti-plant virus activity, but the influence of the 6-position substituent on the activity has not been studied yet, The method of derivatizing the 6-position is also lacking in reports

Method used

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  • Phenanthroindolizidine alkaloid glycosylation product, 6-site derivatization product, and preparation methods and plant virus resistance activities of phenanthroindolizidine alkaloid glycosylation product and 6-site derivatization product
  • Phenanthroindolizidine alkaloid glycosylation product, 6-site derivatization product, and preparation methods and plant virus resistance activities of phenanthroindolizidine alkaloid glycosylation product and 6-site derivatization product
  • Phenanthroindolizidine alkaloid glycosylation product, 6-site derivatization product, and preparation methods and plant virus resistance activities of phenanthroindolizidine alkaloid glycosylation product and 6-site derivatization product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis of (S)-6-O-desmethylantorphine oxyside I-1~I-4 and 14-hydroxy sylphenoxyside I-5~I-6

[0034] Synthesis of (S)-6-O-desmethylantorfenoxoside I-1~I-4

[0035]

[0036] Add (S)-6-O-desmethylantorphine 2 (0.40g, 1.15mmol) to 40mL of dichloromethane, under the protection of argon, add Molecular sieves, stirred at room temperature for 0.5h. Add 0.2mL BF at low temperature 3 ·Et 2 O, stirred for 0.5h, added dropwise a dichloromethane solution of sugar trichloroacetimidate A (or B, C) (0.75g, 1.20mmol), reacted for 4h, TLC monitored the reaction to be complete, added water to quench the reaction, and separated , extracted the aqueous phase with dichloromethane, dried over anhydrous magnesium sulfate, precipitated, and column chromatographed (ethyl acetate-dichloromethane:methanol=30:1) to obtain fully acetylated glycosides. Add the obtained glycosides to 15 mL of methanol, add sodium methoxide to pH = 9-12, stir at room temperature for 1 h, precipit...

Embodiment 2

[0046] Example 2: A method for glycosylation of (S)-6-O-demethylantorphine and 14-hydroxysilimenine using 1,2,3-triazole as a linking arm.

[0047]

[0048] Synthesis of (13aS)-6-O-propargylantorphine (I-28) Dissolve (S)-6-O-desmethylantorphine 2 (0.81 g, 2.33 mmol) in 15 mL of N,N- In dimethylformamide, add Cs 2 CO 3 (0.91g, 2.79mmol), stirred at room temperature for 0.5h, slowly added dropwise a solution of propargyl bromide (2.79mmol) in 10mL N,N-dimethylformamide, and reacted until the reaction was complete as monitored by TLC. Add 30mL of ethyl acetate and 30mL of water, separate the liquid, extract the aqueous phase with ethyl acetate, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter, precipitate, and perform column chromatography (ethyl acetate as eluent ), the white solid product I-28 (0.77g) can be obtained, the yield is 85%, and the melting point is 195-197°C; 1 H NMR (400MHz, CDCl 3 ): δ8.04(br, 1H), 7.91(s, 1H), ...

Embodiment 3

[0063] Example 3: A method for glycosylation of (R) / (S)-6-O-demethylantorphine and 14-hydroxysilicateline with carbamoyloxy as a linking arm.

[0064]

[0065]The alkaloid (R)-6-O-desmethylantorphine (1) or (S)-6-O-desmethylantorphine (2) (0.18 g, 0.52 mmol) was dissolved in dichloromethane (40mL), add 2-deoxy-2-isocyanato-1,3,4,6-tetra-O-acetyl-β-D-glucose (G) (0.27g, 0.62mmol), add 0.4mL Triethylamine, the reaction was complete as detected by TLC, solvent removal, and normal pressure column chromatography (ethyl acetate—dichloromethane:methanol=10:1) to obtain product I-19 or I-20.

[0066] Dissolve 14-hydroxyalkaloid 3 (or 4,5,6) (0.18g, 0.44mmol) in dichloromethane (40mL), add 2-deoxy-2-isocyanato-1,3,4,6 -Tetra-O-acetyl-β-D-glucose (G) (0.76g, 1.76mmol), add 0.4mL triethylamine, TLC detects that the reaction is complete, precipitation, normal pressure column chromatography (ethyl acetate: petroleum Ether=10:1) to obtain product I-21 (or I-22, I-23, I-24).

[0067] (...

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Abstract

The present invention relates to a phenanthroindolizidine alkaloid glycosylation product, a 6-site derivatization product, and preparation methods and plant virus resistance activities of the phenanthroindolizidine alkaloid glycosylation product and the 6-site derivatization product, wherein various groups in the formula are defined in an instruction. According to the present invention, the phenanthroindolizidine alkaloid glycosylation product has characteristics of good light stability, good thermal stability, good water solubility and excellent plant virus resistance, and the glycosylation product and 6-site derivatization product can well inhibit tobacco mosaic virus (TMV). The formula I is as the follow.

Description

technical field [0001] The present invention relates to the glycosylation product of 6-O-demethyl antorphine and 14-hydroxy sylphenine, the 6-position derivative of 6-O-demethyl antorphine, its preparation method and anti- Plant virus activity. Background technique [0002] Phenanthroindolizidine alkaloids mainly exist in Asclepiadaceae, Moraceae, Acanthaceae and Lauraceae plants. This kind of alkaloid has a very wide range of biological activities, especially its unique anticancer activity has attracted widespread attention from synthetic chemists and pharmacologists. Among them, (R)-6-O-desmethylantorphine (1) exhibited better anticancer activity than other phenanthrene and indolizidine alkaloids, while DCB-3503 (3) has different Unique mechanism of action of previous anticancer drugs. For the first time, our research group found that the extract of P. chinensis has a very high inhibitory activity against the extremely harmful tobacco mosaic virus (TMV). Further biologi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/02C07H19/056C07H13/12C07H1/00C07D471/04A01N43/90A01N47/18A01P1/00
Inventor 汪清民吴萌韩贵芳王兹稳刘玉秀王力钟
Owner NANKAI UNIV
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