Derivative of sinomenine with pyrazinc cyclc being connected to C cycle, synthetic method and application

A synthesis method and technology of sinomenine are applied in the fields of sinomenine derivatives with pyrazine ring connected to C ring, synthesis and use thereof, and can solve the problems of large dosage and the like

Inactive Publication Date: 2005-10-26
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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Problems solved by technology

But its dosage is too large, caused by allergic side effects

Method used

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  • Derivative of sinomenine with pyrazinc cyclc being connected to C cycle, synthetic method and application
  • Derivative of sinomenine with pyrazinc cyclc being connected to C cycle, synthetic method and application
  • Derivative of sinomenine with pyrazinc cyclc being connected to C cycle, synthetic method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]

[0051] The chloroform solution of equivalent o-phenylenediamine was added dropwise in the chloroform solution of 0.73g compound 1 (2.3mmol), stirred at room temperature for 5 hours, the reaction solution was concentrated to dryness, and chloroform-petroleum ether recrystallized to obtain 0.65g white solid ( Compound 2), yield 78%.

[0052] 1 H NMR (CDCl 3 , 300MHz): 8.00(1H, m), 7.87(1H, m), 7.61(2H, m), 6.71, 6.61(2H 2d,, J=4.8), 6.07(1H, Brs.,), 5.02(1H, d, J=17.1), 3.71(3H, s), 2.87~3.27(6H, m), 2.58(2H, m), 2.48(3H, s), 2.21(1H, dt, J=2.7, 12.0), 2.10 (1H, J=12.9) 1.92 (1H; dt, J=4.2, 12.6) ppm.

[0053] 13 C NMR (CDCl 3 : CD 3 OD=10∶1,75MHz):153.588,153.264,144.728,144.317,140.826,140.539,130.219,128.910,127.572,127.472,122.279,118.322,109.079,56.270,55.580,46.563,43.712,42.320,41.961,41.914,37.338 , 35.794, 32.903, 22.957ppm.

[0054] IR (KBr): 2932, 1602, 1483, 1400, 1356, 1276, 1228, 1066, 1053, 836, 761 cm-1 MS (EI, m / z): 387 (M + ).

[0055] HRM...

Embodiment 2

[0057]

[0058] An equivalent amount of 3,4-diaminotoluene in chloroform was added dropwise to 1.0 g of compound 1 (3.17 mmol) in chloroform, and stirred at room temperature for 8 hours. The reaction solution was concentrated and separated by column chromatography to obtain 0.9 g of a white solid with one point in TLC, and the yield was 70%. However, the mixture of compounds 3 and 4 was identified by proton nuclear magnetic resonance, and the ratio was compound 3:compound 4 (or compound 4:compound 3)=6:1. It cannot be determined whether compound 3 or compound 4 has the larger amount.

[0059] 1 H NMR (CDCl 3 , 300MHz) (whichever is more in the mixture): 1 H NMR (CDCl 3 , 300MHz): 7.71(2H, m), 7.40(1H, d, J=8.4), 6.60, 6.56(2H, 2d,, J=8.1), 6.30(1H, Brs.,), 5.02(1H, d , J=17.5), 3.67(3H, s), 2.87~3.27(6H, m), 2.55-2.69(2H, m), 2.53(3H, s), 2.48(3H, s), 2.21(1H, dt, J = 2.7, 12.6), 2.1 (1H, d, J = 12.9) 1.91 (; 1H, dt, J = 3.9, 12.0).

[0060] MS (EI, m / z): 401 (M + )...

Embodiment 3

[0062]

[0063] 1.15 g of compound 1 (3.67 mmol) and an equivalent of 4,5-dimethyl-o-phenylenediamine were dissolved in dichloromethane, stirred at room temperature for 5 hours, concentrated and separated by column chromatography to obtain 1.21 g of a white solid (compound 5), Yield 79%.

[0064] 1 H NMR (CDCl 3 , 300MHz): 7.55(1H, s), 7.50(1H, s), 6.57(2H 2d, J=8.3), 6.06(1H, Brs.,), 5.02(1H, d, J=17.0), 3.62( 3H, s), 2.92~3.16(6H, m), 2.55(2H, m), 2.46(3H, s), 2.36(3H, s), 2.31(3H, s), 2.22(1H, dt, J=3.0, 12.9 ), 2.1 (1H, d, J=12.9) 1.91 (1H, dt, J=4.8, 13.2)

[0065] 13 C NMR (CDCl 3 ,75.0MHz)152.777,152.411,145.022,144.637,140.396,140.113,138.829,138.768,131.268,127.657,127.234,123.736,118.701,108.954,77.637,77.215,76.795,56.706,55.904,47.037,44.576,43.109,43.009, 38.327, 36.324, 33.550, 23.407, 20.279, 20.245 ppm.

[0066] IR (KBr): 3005, 2916, 2802, 1604 1483, 1439, 1335, 1274, 1228, 1153, 1104, 1066, 1054, 1023, 989, 867, 857, 792cm -1 .

[0067] MS(EI): 415...

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Abstract

The present invention relates to a sinomenine derivative whose C ring is connected with pyrazine ring, its synthesis method and application. Said invention also provides the structure formula of said sinomenine derivative. Said derivative has stronger inhibition action for cell multiplication of T and B lymphocytes, and can be used for preparing medicine capable of regulating immunity.

Description

technical field [0001] The present invention relates to a sinomenine derivative with a C ring connected to a pyrazine ring, a synthesis method and an application thereof, that is, a sinomenine derivative with a C ring connected to a pyrazine ring, a 1,2-diamino compound and a sinomenine A method for synthesizing a sinomenine derivative whose C ring is connected with a pyrazine ring from the hydrolyzed product of the invention, the derivative has a strong inhibitory effect on the proliferation of T and B lymphocytes, and can be used to prepare drugs for immune regulation. Background technique [0002] Traditional Chinese medicine is the material basis for curing diseases, saving lives, and ensuring people's health. It is a summary of the rich experience of the Chinese working people in fighting diseases for a long time, and has made great contributions to the prosperity of the Chinese nation. [0003] With the development of society and changes in the spectrum of human diseas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/08
Inventor 姚祝军周海滨
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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