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Phenanthrenequinolizidine alkaloid derivatives and their salts and their preparation, anti-plant virus and anti-cancer activities

A technology of phenanthroquinol and risidine, which is applied in the field of phenanthroquinol and risidine alkaloid derivatives and their salts, can solve the problems of photothermal instability, difficulty in repeating, poor water solubility, etc., and achieve excellent resistance The effect of plant virus activity and good anticancer activity

Active Publication Date: 2016-04-20
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] WO03070166 discloses the preparation method of phenanthroquinolizidine derivatives and their application in medicine, but the route is long and the conditions are harsh and difficult to repeat, and it is reported that the structure of phenanthrenequinolizidine derivatives is single, and the activity is mainly Concentrate on two tumor cell lines, KB and HepG2; WO2011049704 discloses the preparation method of phenanthroquinolizidine derivatives and their application in medicine. (R)-Cryptopleurine and its E-ring nitrogen-oxygen-containing derivatives and their anticancer activity; ZL200610129555.1 discloses the application of phenanthroquinolizidine derivatives and their salts in pesticides, because the compound reported in the patent It has the disadvantages of poor water solubility and photothermal instability, and only in vitro activity tests have been carried out

Method used

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  • Phenanthrenequinolizidine alkaloid derivatives and their salts and their preparation, anti-plant virus and anti-cancer activities
  • Phenanthrenequinolizidine alkaloid derivatives and their salts and their preparation, anti-plant virus and anti-cancer activities
  • Phenanthrenequinolizidine alkaloid derivatives and their salts and their preparation, anti-plant virus and anti-cancer activities

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Synthesis of phenanthroquinolizidine alkaloid derivatives I-a-1~I-a-13

[0040] 2,3-Dimethoxy-6-benzyloxy-phenanthrene-[9,10-b]-quinolizidine (I-a-8) and 6-hydroxy-2,3-dimethoxy-phenanthrene -[9,10-b]-quinolizidine (I-a-9) synthesis:

[0041]

[0042] Synthesis of 2-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)methyl acrylate Add 19.6g (0.1mol) 3,4-dimethyl in sequence to a 250mL four-necked reaction flask Oxyphenylacetic acid, 12.2g (0.1mol) 4-methoxybenzaldehyde, 40mL acetic anhydride and 20mL triethylamine were stirred and heated for 20h. The mixture was cooled to room temperature, 60 mL of water was added thereto, reacted for 8 h, filtered, and washed with methanol to obtain a yellow solid, 22.1 g in total, and the above yellow solid, 600 mL of methanol, and 4 g of concentrated sulfuric acid were added to a 1 L four-neck flask, and heated Reaction 12h. The reaction solution was desolvated to obtain a brown solid, which was recrystallized with methano...

Embodiment 2

[0082] Embodiment 2: Synthesis of phenanthroquinolizidine alkaloid derivatives I-b-1~I-b-7 and I-c-1

[0083] 2,3,6,7-Tetrabenzyloxycarbonyloxy-phenanthrene-[9,10-b]-quinolizidine (I-b-1) and 2,3,6,7-tetrahydroxy-phenanthrene- Preparation of [9,10-b]-quinolizidine (I-c-1)

[0084]

[0085] Synthesis of 2,3,6,7-tetrabenzyloxycarbonyloxy-phenanthrene-[9,10-b]-quinolizidine (I-b-1) Add 0.4g (1mmol) to a 250mL one-necked bottle 2,3,6,7-Tetramethoxy-phenanthrene-[9,10-b]-quinolizidine (I-a-7), 80mL dichloromethane, install constant pressure dropping funnel and drying tube, in Add 20mL of dichloromethane and 3mL of boron tribromide into the constant pressure dropping funnel, put the reaction bottle into a low-temperature bath, stir the reaction, and add the dichloromethane solution of boron tribromide dropwise. After the dropwise addition, react for 36h. Add methanol, spin out the reaction solution, add 60mL of water and 60mL of tetrahydrofuran to dissolve the residue, pour it...

Embodiment 3

[0101] Example 3: 2,3,6,7-tetramethoxy-phenanthrene-[9,10-b]-quinolizidine-9-formic acid ethyl ester (I-d-1) and 2,3,6, Preparation of 7-tetramethoxy-phenanthrene-[9,10-b]-quinolizidine-9-methanol (I-d-2)

[0102]

[0103] Synthesis of ethyl 2,3,6,7-tetramethoxy-phenanthrene-[9,10-b]-quinolizidine-9-carboxylate (I-d-1)

[0104] In a 100mL four-neck flask, add 0.8g (2mmol) 2-(2,3,6,7-tetramethoxy-9-phenanthrenylmethyl)-piperidine, 60mL acetonitrile, pass through argon protection, add 2.6 mL50% ethyl glyoxylate solution in toluene, add 0.1mL glacial acetic acid. The reaction was stirred at room temperature for 24h. Add saturated sodium bicarbonate solution for treatment, extract with dichloromethane, wash twice with saturated sodium bicarbonate, then wash once with saturated brine, add anhydrous sodium sulfate to dry, filter and precipitate to obtain a yellow solid 0.9g, yield 83.3%, melting point 167-169°C; 1 HNMR (400MHz, CDCl 3 )δ1.25(t, J=7.2Hz, 3H), 1.41-1.54(m, 2H)...

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Abstract

The present invention relates to phenanthroquinolizidine alkaloid derivatives (I) and their salts (II) and their preparation, anti-plant virus activity and anti-cancer activity. The meaning of each group in the formula can be found in the description. The phenanthrenequinolizidine alkaloid derivative (I) and its salt (II) of the present invention exhibit particularly excellent anti-plant virus activity, and can well inhibit tobacco mosaic virus (TMV). The compound also exhibits good anticancer activity, and can well inhibit human lung adenocarcinoma A-549 and human leukemia HL-60.

Description

technical field [0001] The present invention relates to phenanthroquinolizidine alkaloid derivatives and their salts, their preparation, anti-plant virus and anti-cancer applications. Background technique [0002] Phenanthrenequinolizidine alkaloids mainly exist in natural plants such as Lauraceae, Vitaceae and Urticaceae. Since the first phenanthrene and quinolizidine alkaloid Cryptopleurine was isolated and reported in 1948, so far there are only five such alkaloids: (14aR)-Cryptopleurine, Cryptopleuridine, (14aR)-BoehmeriasinA, BoehmeriasinB and ( 14aR, 15R)-15-Hydroxycryptopleurine was isolated and found. Although the content of this kind of alkaloids is very small in nature, their good biological activities still attract the attention of chemists and pharmacologists. [0003] [0004] WO03070166 discloses the preparation method of phenanthroquinolizidine derivatives and their application in medicine, but the route is long and the conditions are harsh and difficult ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/147C07D471/04A01P1/00A61P35/00A61P35/02
CPCC07D455/03C07D491/147A61P1/00A61P3/00A61P35/00A61P35/02C07D471/04C07D498/14
Inventor 汪清民王兹稳冯安政王力钟刘玉秀崔明波
Owner NANKAI UNIV
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