Phenanthroquinolizidine alkaloid derivatives and salts thereof, and preparation, anti-plant virus activity and anti-cancer activity of phenanthroquinolizidine alkaloid derivatives and salts thereof

A technology of alkaloid derivatives, phenanthroquinol, which is applied in the field of phenanthroquinolizidine alkaloid derivatives and their salts, and can solve the problem of unrepeatable, photothermal instability, and phenanthroquinolizidine derivatives. Single structure and other problems, to achieve good anti-cancer activity, excellent anti-plant virus activity

Active Publication Date: 2014-01-15
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

Method used

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  • Phenanthroquinolizidine alkaloid derivatives and salts thereof, and preparation, anti-plant virus activity and anti-cancer activity of phenanthroquinolizidine alkaloid derivatives and salts thereof
  • Phenanthroquinolizidine alkaloid derivatives and salts thereof, and preparation, anti-plant virus activity and anti-cancer activity of phenanthroquinolizidine alkaloid derivatives and salts thereof
  • Phenanthroquinolizidine alkaloid derivatives and salts thereof, and preparation, anti-plant virus activity and anti-cancer activity of phenanthroquinolizidine alkaloid derivatives and salts thereof

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 methanol...

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 H NMR (400MHz, CDCl 3 )δ1.25(t, J=7.2Hz, 3H), 1.41-1.54(m, 2H...

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Abstract

Provided are phenanthroindolizidine alkaloid derivates and salt thereof as well as preparation, a plant-virus resisting activity, and an anti-cancer activity of phenanthroindolizidine alkaloid derivates and salt thereof. The derivates and the salt thereof have a good plant-virus resisting activity, which is capable of well restraining a tobacco mosaic virus (TMV), and meanwhile, have a good anti-cancer activity, which is capable of well restraining the human lung adenocarcinoma A-549 and the 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 phenanthroquinolizidine alkaloid, Cryptopleurine, was isolated and reported in 1948, so far there are only five such alkaloids: (14aR)-Cryptopleurine, Cryptopleuridine, (14aR)-Boehmeriasin A, Boehmeriasin B and (14aR, 15R)-15-Hydroxycryptopleurine were 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 to ...

Claims

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Application Information

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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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