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Organotin-tetraphenyl ethylene acylhydrazone compound with AIE characteristic as well as preparation method and application of organotin-tetraphenyl ethylene acylhydrazone compound

A technology of tetraphenylethylene acylhydrazone compound and tetraphenylethylene, applied in tin organic compounds, chemical instruments and methods, drug combinations, etc., can solve problems such as luminescence quenching, and achieve good anticancer activity

Pending Publication Date: 2022-08-02
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most organotin compounds exhibit weak fluorescence or aggregation-induced luminescence quenching (ACQ), which poses a great challenge for studying their anticancer mechanisms.

Method used

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  • Organotin-tetraphenyl ethylene acylhydrazone compound with AIE characteristic as well as preparation method and application of organotin-tetraphenyl ethylene acylhydrazone compound
  • Organotin-tetraphenyl ethylene acylhydrazone compound with AIE characteristic as well as preparation method and application of organotin-tetraphenyl ethylene acylhydrazone compound
  • Organotin-tetraphenyl ethylene acylhydrazone compound with AIE characteristic as well as preparation method and application of organotin-tetraphenyl ethylene acylhydrazone compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Under electromagnetic stirring, 0.44 g of triphenyltinhydrazine carbonyl compound (L1) was dissolved in 20 mL of chloroform, and then 0.16 g of chloroform solution of iodine chloride was slowly added dropwise to the above solution under an ice-water bath. Faded, the dropwise addition was completed, and the reaction was continued for 30 min to obtain a colorless solution. The solvent was evaporated under reduced pressure to obtain a colorless viscous substance, which solidified after being placed in a vacuum desiccator for two days. The colorless crystal compound (L2) 0.37 g was recrystallized with chloroform-petroleum ether in a volume ratio of 1:1, and the yield was 93.2 %. Characterization spectra such as figure 1 shown: 1 H NMR (500 MHz, CDCl 3 ) δ 7.98-7.74 (m, 4H), 7.45-7.25 (m, 6H), 2.75-2.42 (m, 2H), 1.79-1.57 (m, 2H).

Embodiment 2

[0052] Under electromagnetic stirring, 0.44 g of triphenyltinhydrazine carbonyl compound (L1) was dissolved in 20 mL of chloroform, and then 0.16 g of the chloroform solution of elemental bromine was slowly added dropwise to the above solution under an ice-water bath, and the color faded immediately. , the dropwise addition was completed, and the reaction was continued for 30 min to obtain a colorless solution. The solvent was evaporated under reduced pressure to obtain a colorless viscous substance, which solidified after being placed in a vacuum desiccator for two days. The colorless crystal compound (L3) 0.41 g was recrystallized with a volume ratio of 1:1 chloroform-petroleum ether, and the yield was 93.2 %. Characterization spectra such as figure 2 shown: 1 H NMR (500 MHz, CDCl 3 ) δ 7.96-7.78 (m, 4H), 7.42-7.31 (m, 6H), 2.69 (dt, 3 J ( 119 Sn-H)=15.3, 7.3 Hz, 2H), 1.91-1.68 (m, 2H).

Embodiment 3

[0054] Under electromagnetic stirring, 0.44 g of triphenyltinhydrazine carbonyl compound (L1) was dissolved in 20 mL of chloroform, and then 0.25 g of the chloroform solution of elemental iodine was slowly added dropwise to the above solution under an ice-water bath, and the color faded immediately. , the dropwise addition was completed, and the reaction was continued for 30 min to obtain a colorless solution. The solvent was evaporated under reduced pressure to obtain a colorless viscous substance, which solidified after being placed in a vacuum desiccator for two days. The colorless crystal compound (L4) 0.42 g was recrystallized with chloroform-petroleum ether in a volume ratio of 1:1, and the yield was 85.7 g %. Characterization spectra such as image 3 shown: 1 H NMR (500 MHz, CDCl 3 ) δ 7.99-7.78 (m, 4H), 7.47-7.27 (m, 6H), 2.66 (t, 3 J ( 119 Sn-H)= 10.0 Hz, 2H), 1.90 (t, 3 J ( 119 Sn-H) =10.0 Hz, 2H).

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Abstract

The invention discloses an organic tin-tetraphenyl ethylene acylhydrazone compound with an aggregation-induced emission (AIE) characteristic as well as a preparation method and anti-cancer application of the organic tin-tetraphenyl ethylene acylhydrazone compound. The structural formula is shown as a formula (I), and R is phenyl, chlorine, bromine or iodine. According to the present invention, the growth inhibition rates of the target compound on human alveolar basal epithelial cancer cells (A549), cervical cancer cells (Hela) and human lung normal epithelial cells (BEAS-2B) are tested, and comparison results show that the target compound shows the potential anti-cancer activity; the anticancer activity of the compound is effectively improved along with the substituent R phenyl-iodine-bromine-chlorine. In addition, the target compound shows unique AIE luminescence characteristics and relatively high solid-state absolute fluorescence quantum yield. The target compound can target mitochondria of A549 cells and cause reduction of mitochondrial membrane potential, and shows anti-cancer activity.

Description

technical field [0001] The invention relates to a metal organic compound, in particular to an organotin-tetrastyrene acylhydrazone compound with AIE characteristics, a preparation method and application thereof, and belongs to the field of chemical pharmacy. Background technique [0002] Cancer, a malignant tumor, is the second leading cause of human death in the world after cardiovascular and cerebrovascular diseases. It remains one of the most challenging diseases due to the lack of a better way to treat it ( Cancer. Res .2012, 72, 304-314). Platinum-based chemicals such as cisplatin have played a huge role in clinical applications, fully demonstrating the great potential of metal compounds in exerting anticancer activity. However, the huge defects of platinum drugs (drug resistance, nephrotoxicity, etc.) have prompted the development of new metal anticancer drugs. Among them, organotin anticancer compounds are a large category that cannot be ignored, which show better ...

Claims

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Application Information

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IPC IPC(8): C07F7/22C09K11/06A61P35/00
CPCC07F7/2208C09K11/06A61P35/00C09K2211/188C07B2200/13Y02E10/549
Inventor 刘西成刘哲李翘楚陈光孙心卓任雪艳
Owner QUFU NORMAL UNIV
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