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Sanguinarine derivatives and synthesis method and use thereof

A synthetic method and technology of sanguinarine, applied in the field of sanguinarine derivatives and synthesis, can solve problems such as sheath blight, achieve low residue, simple synthesis method, and excellent effect of inhibiting rice sheath blight activity

Inactive Publication Date: 2011-04-13
NANKAI UNIV
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  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, there is no report on synthesizing its derivatives with sanguinarine as a raw material and applying it to kill rice sheath blight at home and abroad

Method used

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  • Sanguinarine derivatives and synthesis method and use thereof
  • Sanguinarine derivatives and synthesis method and use thereof
  • Sanguinarine derivatives and synthesis method and use thereof

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Embodiment Construction

[0016] Compound 1: 110 mg of sanguinarine was dissolved in 5 ml of isopropanol, 5 ml of 0.1 N NaOH solution was added, and stirred at room temperature for 24 hours. Phenomenon: The orange yellow gradually disappears, and a white solid appears. Suction filtration and washing with water gave the product with a yield of 65%. Mp: 247-250°C. 1 H NMR (CDCl 3 , 400MHz) (δ, ppm): 7.76(d, J=8.4Hz, 1H), 7.65(s, 1H), 7.47(d, J=8.4Hz, 1H), 7.39(d, J=8Hz, 1H) , 7.12(s, 1H), 6.91(d, J=8.4Hz, 1H), 6.11(s, 1H), 6.06(s, 3H), 5.53(s, 1H), 4.33(quint, J 1 =6.4Hz,J 2 =6Hz), 2.73(s, 3H), 1.28(d, J=6Hz, 1H), 0.90(d, J=6.4Hz, 1H). 13 C NMR (CDCl 3 , 100MHz) (δ, ppm): 148.0, 147.3, 145.1, 138.7, 130.9, 126.9, 125.9, 123.6, 123.0, 120.3, 116.4, 113.6, 108.6, 104.6, 101.7, 101.0, 100.6, 82.3, 46.8, 2, 3 , 21.2. HRMS (ESI): m / z (%) calcd for [C 23 h 21 NO 5 +Na] + : 414.1312; found: 414.1316.

[0017] Compound 2: 110 mg of sanguinarine in 10 ml of acetonitrile, 0.1 g of p-methylaniline, stir...

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Abstract

The invention relates to sanguinarine derivatives and a synthesis method and use thereof. In the invention, 5-isopropoxy-5,6-dihydrosanguinarine, 5-p-methylphenylamino-5,6-dihydrosanguinarine and 5-benzylamino-5,6-dihydrosanguinarine are synthesized by using sanguinarine as a raw material under different conditions. The bactericidal activities of the three compounds are measured at different concentrations, and corresponding EC50 values are calculated. Compared with the conventional bactericide, the sanguinarine derivatives have the characteristics of high degradability, low residue and the like and can be synthesized by a simple and economic method. Thus, the sanguinarine derivatives are valuable bactericide pilot compounds and can be used for preventing and controlling rhizoctonia solani.

Description

technical field [0001] The invention relates to a sanguinarine derivative, a synthesis method and the application of its bactericidal activity. Background technique [0002] As we all know, alkaloids are the earliest studied natural products, which have extensive and strong physiological activities on human body, animals or agricultural pests. It is one of the most popular fields of natural product research and in-depth development and application to use monomeric substances with excellent activity as template compounds to systematically modify or modify their structure and conduct structure-activity relationship (QSAR) research. Sanguinarine (C 20 h 14 NO 4 , Sanguinarine) is a naturally occurring benzophenanthridine alkaloid with anticancer, insecticidal, bactericidal, anti-inflammatory and other activities. Due to the presence of sanguinarine C=N + With an ionic double bond, nucleophiles readily add to the C atom to form a pseudobase. In addition, 5-methoxy-5,6-dihy...

Claims

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Application Information

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IPC IPC(8): C07D491/153A01N43/90A01P3/00
Inventor 徐效华吕培黄康伦谢龙观
Owner NANKAI UNIV
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