C14-position aminated derivatives of phenanthrene and indolizidine alkaloids and their preparation and anti-plant virus activity

A technology of phenanthroindolizidine and alkaloids, which is applied in the field of preparation and anti-plant virus activity, can solve the problems of difficult repetition of synthesis methods, single structure of phenanthroquinolizidine derivatives, single structure type, and the like, To achieve good anti-plant virus activity, the effect of inhibiting tobacco mosaic virus

Active Publication Date: 2015-12-16
NANKAI UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0004] WO03070166 discloses the preparation method of phenanthrene and quinolizidine 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 phenanthrene and quinolizidine The derivative has a single structure, and its activity is mainly concentrated in two tumor cell lines, KB and HepG2; ZL200710058173.9 discloses the preparation of phenanthrene and indolizidine derivatives. The synthesis method is very efficient, but it cannot be used to prepare C14-position aminated Derivatives; WO2010099740 discloses the preparation of 13aS-phenanthrene and indolizidine C14-position amino derivatives and its application in medicine, but the synthesis method is difficult to repeat, and the structure type is relatively single, only 3,6 on the phenanthrene ring are reported. , 13aS-phenanthroindolizidine C14-amino derivatives containing methoxy at the 7-position, the application is limited to anti-tumor applications; we reported (13aS, 14S)-phenanthroindolizidine in our previous work Efficient synthesis of indolizidine C14 amino derivatives (Synthesis.2011, 6, 979-983), but only a single configuration was studied, and this method cannot be used to prepare isomers of four configurations

Method used

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  • C14-position aminated derivatives of phenanthrene and indolizidine alkaloids and their preparation and anti-plant virus activity
  • C14-position aminated derivatives of phenanthrene and indolizidine alkaloids and their preparation and anti-plant virus activity
  • C14-position aminated derivatives of phenanthrene and indolizidine alkaloids and their preparation and anti-plant virus activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Synthesis of 14-aminophenanthrene and indolizidine alkaloid derivatives 1-19

[0020] Synthesis of (±)-14-aminosilicate (1) and (±)-14-benzamidosilicate (10) (see Equation 3)

[0021]

[0022] Synthesis of (±)-1-(2,3,6,7-tetramethoxy-10-bromo-9-phenanthrenemethyl)pyrrole-2-carboxamide

[0023] Add 2,3,6,7-tetramethoxy-10-bromo-9-bromomethylphenanthrene (10.64mmol), (±)-pyrrole-2-carboxamide (12.77mmol) into a 250mL single-necked bottle, without Potassium carbonate in water (15.96mmol), N,N-dimethylformamide (DMF) (150mL), heated for 8 hours, desolvated, and the residue was washed with saturated brine to obtain a white solid product (±)-1-(2 , 3,6,7-tetramethoxy-10-bromo-9-phenanthrenemethyl)pyrrole-2-carboxamide (4.93g), yield 93%, melting point 238-239°C; 1 HNMR (400MHz, CDCl 3 )δ7.83(s, 1H), 7.75(s, 1H), 7.73(s, 1H), 7.64(s, 1H), 6.69(d, J=4.4Hz, 1H), 4.81(d, J=4.4 Hz, 1H), 4.62(d, J=13.2Hz, 1H), 4.48(d, J=13.2Hz, 1H, 4.12(s, 6H), 4.07(s, 3H), 4.05(s...

Embodiment 2

[0065] Example 2: Synthesis of 14-aminophenanthrene and indolizidine alkaloid derivatives 20-39

[0066] (13aR, 14R)-14-n-butylamine-2,3,6,7-tetramethoxyphenanthrene[9,10-b]-11-indolizidinone (28), (13aR, 14S )-14-n-butylamine-2,3,6,7-tetramethoxyphenanthrene[9,10-b]-11-indolizidone (29), (13aR, 14R)-14- Synthesis of n-butylaminosylmenine (32), (13aR, 14S)-14-n-butylaminosylphine (33) (see Equation 4)

[0067]

[0068]

[0069] Synthesis of (R)-N-(2,3,6,7-tetramethoxy-10-phenanthrenemethyl)pyroglutamic acid methyl ester

[0070] Dissolve 2,3,6,7-tetramethoxy-10-phenanthrene methyl bromide (4.0 g, 10.2 mmol) in N, N-dimethylformamide (100 mL), add D- Dimethyl glutamate hydrochloride (D-BMPAC) (2.98g, 14.1mmol) was solid. After stirring for 10 minutes, anhydrous potassium carbonate powder (2.08g) was added in one batch, and stirred at room temperature for 10 hours. N, N-dimethylformamide was distilled off under reduced pressure, dichloromethane and water were added, the...

Embodiment 3

[0107] Example 3: Research on the physicochemical properties of the C14-position aminated derivative (I) of the preferred phenanthroindolizidine alkaloid:

[0108] The chemical structural formula of preferred phenanthrene and indolizidine alkaloid C14 position amination derivative (I):

[0109]

[0110]

[0111] Compared with the known compounds, the above-mentioned preferred compounds have outstanding advantages, which are embodied in: (1) the light and thermal stability are significantly enhanced. Under the same conditions, they are irradiated with fluorescent lamps or controlled at 80°C for 24 hours and then qualitatively detected by NMR. No change occurred, while the control sample (R)-Antofine was mostly decomposed. (2) The water solubility is enhanced, the control sample (R)-Antofine is almost insoluble in water, while the preferred compound improves the water solubility. The above two points play a vital role in the application of compounds in pesticides.

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Abstract

Disclosed are phenanthroindolizidine alkaloid C14 aminated derivatives and the preparation and anti-plant virus activity thereof; the above-mentioned compounds have good anti-plant virus activity and can effectively inhibit the tobacco mosaic virus.

Description

technical field [0001] The present invention relates to phenanthrene and indolizidine alkaloid C14 position amination derivatives and their preparation and anti-plant virus activity. Background technique [0002] Plant viruses are not only of various types, but also widely distributed. Virus diseases are the second largest type of plant diseases after fungi in agricultural production. Because viruses are absolutely parasitic in plant cells, the substances, energy and places required for their replication are completely dependent on the host, and plants do not have a complete immune metabolism system, making the prevention and treatment of plant virus diseases particularly difficult, known as "plant cancer". The annual economic loss of crops caused by plant virus diseases in the world reaches 20 billion U.S. dollars, and the losses to my country also reach several hundred million yuan (Vegetables, 8, 30-32, 2010). Diseases of food crops caused by viruses include rice dwarf d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A01P1/00
CPCC07D471/04
Inventor 汪清民王兹稳王蕾王力钟刘玉秀
Owner NANKAI UNIV
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