Purpose of substituent phenyl furaldehyde thiosemicarbazone compound as insect tyrosinase inhibitor

A technology of phenylfuran formaldehyde thiosemicarbazide and tyrosinase, which is applied in the directions of insecticides, animal repellents, plant growth regulators, etc., can solve the problem that L-ascorbic acid has unstable chemical properties, obvious side effects, and inhibits Problems such as poor performance

Inactive Publication Date: 2010-06-30
CHINA AGRI UNIV
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  • Abstract
  • Description
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Problems solved by technology

Currently known tyrosinase inhibitors mainly include arbutin, kojic acid, L-ascorbic acid, hydroquinone, tropolone, etc. (Journal of Xiamen University, 2007, 46(2): 274-281), but these inhibitors There are various deficiencies in the drug: although hydroquinone has a high inhibitory activity, it is more irritating to the skin, and is currently banned in many countries and regions; tropolone has high inhibitory activity, but its use is limited due to obvious side effects. Applications in the field of pharmacy (Bioorganic & Medicinal Chemistry, 16(2008) 1096-1102); kojic acid and arbutin have poor inhibitory effects, and L-ascorbic acid has shortcomings such as unstable chemical properties; in addition, there are many plant extracts in the pharmaceutical industry Most of them are extracts of Chinese medicinal plants, such as the inhibition rate of Tribulus terrestris extract is 43.8% (West China Pharmaceutical Journal, 2006, 21 (1): 050-052)
In addition, Barsanti, Paul et al. reported that the substituent was 4-OCH 3 , 4-F, 4-Cl, 3-Cl, etc. antiviral and immunoenhancing functions of such compounds (WO2004060308), Xiaohui Du et al. reported that the substituents are 4-Cl, 4-Br, 3-Cl, 2- OCH 3 The trypanosomal cysteine ​​protease inhibitory activity of this type of compound (J.Med.Chem.2002,45,26952707), there is no report about the purposes of this type of compound as insect tyrosinase inhibitor

Method used

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  • Purpose of substituent phenyl furaldehyde thiosemicarbazone compound as insect tyrosinase inhibitor

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Embodiment 1

[0014] Embodiment 1: the present invention takes new compound Im as example, illustrates the synthetic method of Im

[0015] Preparation of Im

[0016] Add 33g (0.1mol) of 2,4-,6-tribromoaniline, 20ml of water, and 30ml of concentrated hydrochloric acid into a 500ml four-necked flask, and stir to dissolve the solid. Then the temperature was cooled to zero in an ice bath, and 20 ml of aqueous solution of 7.0 g of sodium nitrite was slowly added dropwise. After the dropwise addition was completed, the mixture was reacted at room temperature for 40 min. Add 50ml of water, 30ml of acetone solution of 10g furfural, and 8ml of aqueous solution of 2.54g copper chloride, react at 20-25°C, add saturated sodium acetate solution dropwise until the pH reaches about 4, stop stirring, and filter with suction to obtain a yellow-brown solid. Sequentially recrystallized from petroleum ether and ethanol to obtain 9.6 g of yellow solid with a yield of 23.5%.

[0017] Add 1 g of a (2.45 mmol) o...

Embodiment 2

[0019] Embodiment 2 General formula (I) compound of the present invention, except Im, all the other compounds are known compounds, can be according to literature (Collection Czechoslov Chem Commun, 1974,39:767~771, J.Med.Chem .2002, 45, 2695-2707) described method preparation.

Embodiment 3

[0020] Example 3 Determination of the inhibitory rate of substituted phenylfuran formaldehyde thiosemicarbazones on cotton bollworm tyrosinase

[0021] a. Enzyme solution is prepared in a pre-cooled glass homogenizer in the ice-water mixture. Add one 5th instar cotton bollworm larvae, 1ml 0.1mol / L, pH=6.5 phosphate buffer, fully homogenate, and place in a centrifuge Centrifuge at a speed of 10,000×g for 15 minutes, and after suction filtration, take the supernatant in an ice bath for later use.

[0022] b. Preparation of test samples Dissolve the above compound in 1ml of DMSO, and make a 4mg / ml solution (mother solution), and dilute to different times according to the inhibition of different samples. Kojic acid and tropolone were used as control agents.

[0023] c. Determination of the compound's ability to inhibit tyrosinase activity of cotton bollworm The reaction system is 1 mL. Add 0.790mL of 0.1mol / L, pH=6.5 phosphate buffer solution, 0.05mL of enzyme solution, 10μL of ...

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PUM

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Abstract

The invention provides a new purpose of a substituent phenyl furaldehyde thiosemicarbazone compound (I) as an insect tyrosinase inhibitor to prevent and control cotton bollworms as. A study on the substituent phenyl furaldehyde thiosemicarbazone compound in inhibiting the activity of cotton bollworm tyrosinase proves that the compound has good function of inhibiting insect tyrosinase and can be used for preventing and controlling pests as the insect tyrosinase inhibitor. In the invention, R refers to 2-Br, 4-Br, 3-F, 4-F, 2-C1, 3-C1, 4-C1, 2-NO2, 3-NO2, 4-NO2, 2, 5-C12, 2, 4-F2, 2, 4, 6-Br3, 2, 4-NO2.

Description

technical field [0001] The invention relates to a new application of substituted phenylfuran formaldehyde thiosemicarbazone compounds, in particular to the application of this type of compound as an insect tyrosinase inhibitor. Background technique [0002] Tyrosinase (tyrosinase), also known as polyphenol oxidase (polyphenol oxidase, PPO or phenoloxidase, P0), widely exists in animals, plants and microorganisms. Tyrosinase is a divalent copper ion (Cu 2+ ) is a metalloenzyme combined with enzyme protein, which has the dual functions of oxygenase and oxidase. It can oxygenate monophenols into diphenols, and can also oxidize polyphenols such as diphenols into quinones, and then generate melanin ( J. Agric. Food Chem., 1996, 44(3): 631-653) [0003] As the key enzyme of melanin synthesis in organisms, tyrosinase is closely related to physiological processes such as insect wound healing, immunity, and the formation of new epidermis; at the same time, it is also associated wit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N47/34C07D307/52A01P7/04
Inventor 杨新玲王振梁沛董玮徐焱凌云
Owner CHINA AGRI UNIV
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