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3-substituted phenyl propionaldehyde thiosemicarbazone compounds, and preparation method and application thereof

A compound and 3-br technology, applied in the field of 3-substituted phenylpropionaldehyde thiosemicarbazide compounds, can solve the problems of unstable chemical properties of L-ascorbic acid, obvious side effects, poor inhibitory effect and the like

Inactive Publication Date: 2011-11-02
CHINA AGRI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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. Application in the field of pharmacy (Bioorganic & Medicinal Chemistry, 2008, 16: 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)
[0005] People such as Liu Chunyan of China Agricultural University (Pesticides, 2004, 43 (11): 497-500) found that when studying the inhibitory effect of pesticides on housefly tyrosinase, the inhibitory concentration of phenylthiourea to housefly (IC 50 ) value is 0.15μM, which is a specific inhibitor of tyrosinase, while parathion, phoxim, methomyl, propoxur, imidacloprid and abamectin have no obvious inhibitory effect on housefly tyrosinase

Method used

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  • 3-substituted phenyl propionaldehyde thiosemicarbazone compounds, and preparation method and application thereof
  • 3-substituted phenyl propionaldehyde thiosemicarbazone compounds, and preparation method and application thereof
  • 3-substituted phenyl propionaldehyde thiosemicarbazone compounds, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Example 1: Preparation of 3-(2,4-dichlorophenyl)-propionaldehyde thiosemicarbazone (S102)

[0024] In the 50mL there-necked flask, add 0.22g (1.09mmol) compound shown in formula II (R is 2, the dichloro that 4 positions replace) 3-(2,4-dichlorophenyl)-propionaldehyde, 20mL organic solvent ethanol and 0.11g (1.2mmol) of thiosemicarbazide, 0.6mg (0.01mmol) of acidic compound acetic acid was added at one time, heated to 78°C under reflux for condensation reaction for 5 hours, and then stopped the reaction. The reaction solution was spin-dried and recrystallized from ethanol to obtain 0.2 g of white granular solid, yield: 66%. The appearance and fusing point of this white granular solid product are shown in Table 1, and its 1 H NMR spectrum data are shown in Table 2. It can be seen from Table 2 that the product has a correct structure and is a compound shown in Formula I, numbered S102.

[0025]

[0026] (Formula I)

[0027] Among them, R is 2,4-Cl 2 .

[0028] Accor...

Embodiment 2

[0029] Example 2: Preparation of 3-(4-chlorophenyl)-propionaldehyde thiosemicarbazone (S103)

[0030] Add 0.42g (2.50mmol) compound shown in formula II (R is 4-substituted chlorine) 3-(4-chlorophenyl)-propionaldehyde in 50mL three-necked flask, 10mL organic solvent ethanol and 0.22g (2.42mmol) amino Thiourea, add 6 mg (0.1 mmol) of acetic acid compound, heat to 78 ° C under reflux for condensation reaction for 2 hours, stop the reaction. The reaction solution was spin-dried, and recrystallized from ethanol to obtain 0.49 g of white crystals, with a yield of 82%. The appearance and fusing point of this white crystal product are shown in Table 1, and its 1 H NMR spectrum data are shown in Table 2. It can be seen from Table 2 that the product has a correct structure and is a compound shown in Formula I, numbered S103.

[0031]

[0032] (Formula I)

[0033] Wherein, R is 4-Cl.

[0034] According to the same method as above for the preparation of compound S103, only the com...

Embodiment 3

[0041] Example 3: 3-substituted phenylpropionaldehyde thiosemicarbazones inhibit activity of cotton bollworm tyrosinase

[0042] Enzyme solution preparation: add 1 head of 5th instar cotton bollworm larvae to a glass homogenizer pre-cooled in ice-water mixture, 1ml 0.1mol / l, phosphate buffer saline solution with pH value of 6.5, fully homogenate, and place in a centrifuge Centrifuge at a speed of 10800 rpm for 15 minutes, and after suction filtration, take the supernatant in an ice bath for later use.

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Abstract

The invention discloses 3-substituted phenyl propionaldehyde thiosemicarbazone compounds, and a preparation method and application thereof. The structures of the compounds are shown as a formula I, wherein R is any one of 4-F, 4-Cl, 2-Cl, 2,4-Cl2, 4-OCH3, 2-OCH3, 3-OCH3, 4-OC2H5, 4-NO2, 2-NO2, 4-CH3, 4-isopropyl, 3-Br and 2,4-dimethoxy. The preparation method comprises the following step of performing condensation reaction on substituted phenyl propionaldehyde shown as a formula II with thiosemicarbazide in an organic solvent in the presence of an acidic compound to obtain the 3-substituted phenyl propionaldehyde thiosemicarbazone compounds. The research on inhibition activity of heliothis armigera tyrosinase by the compounds of the formula I proves that the compounds have better inhibition effect on the heliothis armigera tyrosinase and can serve as an insect tyrosinase inhibitor for preventing and controlling pests.

Description

technical field [0001] The invention relates to a 3-substituted phenylpropionaldehyde thiosemicarbazone compound, a preparation method and application thereof. Background technique [0002] Tyrosinase (tyrosinase), also known as polyphenol oxidase (phenoloxidase), widely exists in animals, plants and microorganisms. It can catalyze two distinct melanin synthesis reactions: one is the hydroxylation of tyrosinase catalyzed by monophenolase, and the other is the oxidation reaction of L-DOPA to o-dopaquinone catalyzed by bisphenolase ( Cell. Mol. Life Sci., 2005, 62: 1707-1723). [0003] Tyrosinase has important physiological functions in organisms, for example, it is related to the occurrence of human freckles, brown spots and other diseases such as excessive melanin deposition, it is related to molt and wound healing of insects, and it is related to enzymatic browning of fruits and vegetables. Therefore, research on efficient tyrosinase inhibitors is becoming more and more i...

Claims

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Application Information

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IPC IPC(8): C07C337/08A01N47/34A01P7/04
Inventor 凌云徐焱杨新玲梁沛王振董玮邢静
Owner CHINA AGRI UNIV
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