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Harmaline amide compound as well as preparation method and application thereof

A technology of salsaline amide and compound, which is applied in the field of salsaline amide compounds and their preparation, can solve problems such as in-depth system derivation synthesis, structure-activity relationship research, and significant application significance, achieving significant antibacterial activity, Simple structure and high product purity

Active Publication Date: 2015-05-20
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, the current research has not gone deep into the derivation synthesis and structure-activity relationship research of the system.
There are few studies on the synthesis of harmine and its related compounds, and the substances extracted from nature cannot meet a large number of needs at all. The application of the compound is of great significance

Method used

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  • Harmaline amide compound as well as preparation method and application thereof
  • Harmaline amide compound as well as preparation method and application thereof
  • Harmaline amide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Synthesis of N,N-diethyl-1-phenyl--β-carboline-3-amide (6a)

[0041] 1. Step A: Synthesis of 1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2)

[0042] Weigh 20.4g of L-tryptophan (0.1mol) into a three-neck flask equipped with an electric heating mantle and electric stirrer, add 100mL of glacial acetic acid and 12.25g of benzaldehyde (0.12mol) while stirring, and stir at room temperature for 15min. Raise the temperature to 80-100°C and react for 10 hours. TLC traces until the tryptophan disappears. Stop heating. Cool to room temperature and a precipitate forms. Filter and concentrate the filtrate under reduced pressure to remove excess acetic acid and water to obtain a large number of light brown flakes. , and washed with water to obtain a white product, namely 1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, with a yield of 85%.

[0043] 2. Step B: Synthesis of 1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester (3)...

Embodiment 2

[0053] Example 2 Synthesis of N,N-diethyl-1-methyl-β-carboline-3-amide (7b)

[0054] 1, operation is the same as embodiment 1, only in step A replaces benzaldehyde with acetaldehyde.

[0055] 2. The product detection data are as follows: Yield: 84%; Melting point: 168-170°C; IR (KBr) ν: 3457, 2946, 1633; 1 H-NMR (500MHz, DMSO- d 6 ) δ: 1.19-1.22 (m, 6H, CH 3 ), 2.87 (s, 3H, 1-CH 3 ), 3.49-3.52 (m, J =12.5Hz, 4H, CH 2 ), 7.31 (t, J =15Hz, 1H, 6-H), 7.60 (dd, J =15Hz, 1H, 7-H), 7.67 (t,J =8.5Hz, 1H, 8-H), 8.37 (d, J =7.5Hz, 1H, 5-H), 8.48 (s, 1H, 4-H), 11.82 (s, 1H, 9-NH).

Embodiment 3

[0056] Example 3 Synthesis of N,N-diethyl-β-carboline-3-amide (7c)

[0057] 1, operation is the same as embodiment 1, only in step A replaces benzaldehyde with formaldehyde.

[0058] 2. The product detection data are as follows: Yield: 75%; Melting point: 174-176°C; IR (KBr) ν: 3167, 2977, 2928, 1593, 1096; 1 H-NMR (500MHz, DMSO- d 6 ) δ: 1.19-1.22 (m, 6H, CH 3 ), 3.49-3.51 (m, 4H, CH 2 ), 7.29 (t, J =14.5Hz, 1H, 6-H), 7.63 (dd, J =14.5Hz, 1H, 7-H), 7.73 (d, J =8.5Hz, 1H, 8-H), 8.39 (d, J =8.5Hz, 1H, 5-H), 8.49 (s, 1H, 4-H), 9.05 (s, 1H, 1-H), 11.79 (s, 1H, 9-NH).

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Abstract

The invention discloses a novel harmaline amide compound, a preparation method of the compound and an application of the compound in preparation of pesticides. The structural formula of the harmaline amide compound is shown as a formula (I); the structural formula is as shown in the specification, wherein in the formula (I), R1 is selected from hydrogen, methyl, phenyl, 2,4,5-trimethoxyphenyl, p-methoxyphenyl, p-trifluoromethylphenyl or p-chlorophenyl; R2 is selected from hydrogen or bromine; R3 is selected from hydrogen or ethyl; and R4 is selected from ethyl, 2-pyridyl, o-chlorophenyl, 4,6-dimethylpyrimidyl or p-trifluoromethylphenyl. The compound has good inhibitory activities on rhizoctonia solani, collectotrichum musae, grey mould germ of strawberry, fusarium oxyspirum F sp niveum and alternaria solani and has good application prospects in control of important agricultural pests. In addition, the artificial synthesis process is simple, the product purity is high, and the compound is suitable for large-scale industrial application.

Description

technical field [0001] The invention belongs to the technical field of pesticides. More specifically, it relates to a camelamide compound and its preparation method and application. Background technique [0002] Cameline is a plant from Tribulus terrestris in my country ( Peganum harmala L . ), which is a kind of β-carboline alkaloid extracted and isolated from ), which has various biological activities such as anticancer, insecticidal, bacteriostatic and antiviral, and has attracted much attention from researchers at home and abroad. In recent years, the research on salicine mainly focuses on the anti-tumor aspect, and in-depth research has been carried out on structural modification, anti-tumor structure-activity relationship, and mechanism of action ((1) Pan Qichao, et al. cancer , 1985, 4 , 192-194; (2) Cao Jun, et al. cancer , 1993, 12 , 214-216; (3) Amy M.D., et al. Bioorganic & Medicinal Chemistry Letters , 2001, 11 , 1251-1255; (4) Cao R.H., et al. Eur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A01P3/00
CPCA01N43/90C07D471/04
Inventor 钟国华刘婕张智军胡美英曾勇
Owner SOUTH CHINA AGRI UNIV
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