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Gold complex taking o-vanillin thiosemicarbazone as ligand and synthesis method thereof

A technology of o-vanillin thiosemicarbazone and gold complexes, which can be applied in the direction of gold organic compounds, 1/11 organic compounds without C-metal bonds, drug combinations, etc., and can solve problems such as insufficient stability

Inactive Publication Date: 2021-01-22
GUANGXI NORMAL UNIV
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  • Claims
  • Application Information

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Problems solved by technology

Many Au(Ⅲ) complexes do show good anti-tumor activity in vitro, but they are not stable enough under near-physiological conditions is a serious defect. O-vanillin thiosemicarbazone is a ligand with multiple coordination sites. It has a strong affinity for transition elements, and Au(Ⅲ) can form very stable complexes with it.

Method used

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  • Gold complex taking o-vanillin thiosemicarbazone as ligand and synthesis method thereof
  • Gold complex taking o-vanillin thiosemicarbazone as ligand and synthesis method thereof
  • Gold complex taking o-vanillin thiosemicarbazone as ligand and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0027] The synthesis of C1 gold complexes, the specific synthesis method is:

[0028] (1) Dissolve 3 mmol of thiosemicarbazide in 15 ml of methanol, then add 3 mmol of o-vanillin, reflux at 65°C for 4 hours, filter, and the filtrate evaporates at room temperature, white powdery crystals precipitate out, wash 2-3 times with absolute ethanol to obtain the compound body L1;

[0029] Yield: 534.63mg, 79.11%, C 9 h 13 N 3 o 2 S: C, 48.18; H, 4.73; N, 18.41; O, 14.54, S, 14.09. Found: C, 47.99; H, 4.92; N, 18.65; O, 14.20. -1 :1498.55(C=C), 3462.02(s, amide), 3032.69(m, aromatic hydrogen), 1617(s), 1262.95(m, C=N), 1119.19(s, thioamide), 1458.58(m, C-H) ,768.47(m,C=S),3462.02(s,hydroxide radical),1058.70(s,C-O);

[0030] (2) Dissolve 0.1 mmol of ligand L1 obtained in step (1) in 10 mL of methanol, and add 0.1 mmol of Na[AuCl 4 ]·2H 2 O, stir at room temperature for 4-6 hours, filter to obtain a black precipitate, wash the precipitate with ether 3 times, 4 mL each time, dry i...

Embodiment 2

[0033] The synthesis of C2 gold complexes, the specific synthesis method is:

[0034] (1) Dissolve 3 mmol of 4-methylthiosemicarbazide in 15 mL of methanol, then add 3 mmol of o-vanillin, reflux at 65°C for 4 hours, filter, and the filtrate evaporates at room temperature, white flocculent crystals precipitate out, wash with anhydrous ether for 2- Ligand L2 was obtained 3 times;

[0035] Yield: 517.25mg, 72.12%, C 10 h 13 N 3 o 2 S: C,49.88; H,5.69; N,17.09; O,13.74; S,13.50, found: C,50.19; H,5.48; N,17.56; O,13.37; S,13.40; IR,cm -1 :1481,1606.8(C=C),3000.25(s,amide),3032.69(m,aromatic hydrogen),1617(s),1276(m,C=N),1157.42(s,thioamide),1361.90,1488.48( m, C-H), 756.24 (m, C=S), 3308.50 (s, hydroxideradical), 1276.00 (s, C-O);

[0036] (2) Dissolve 0.1 mmol of L2 obtained in step (1) in 10 mL of methanol, and add 0.1 mmol of Na[AuCl 4 ]·2H 2 O, stirred at room temperature for 4-6h, the product after the reaction is a brownish-yellow precipitate, washed with ether for 2...

Embodiment 3

[0039] The synthesis of C3 gold complexes, the specific synthesis method is:

[0040] (1) Dissolve 3 mmol of 4-phenylthiosemicarbazide in 15 mL of methanol, then add 3 mmol of o-vanillin, reflux at 65°C for 4 hours, filter, and the filtrate evaporates at room temperature, and white powdery crystals precipitate, wash with anhydrous ether for 2- Ligand L3 was obtained 3 times;

[0041] Yield: 705.63mg, 78.12%, C 15 h 15 N 3 o 2 S: C, 59.58; H, 5.30; N, 13.90; O, 10.55; S, 10.71, found: C, 59.78; H, 5.02; N, 13.94; O, 10.62; C=C), 694.71(s, amide), 3057.32, 1862.10(m, aromatic hydrogen), 1281.94(m, C=N), 1166.83(s, thioamide), 1463.00(m, C-H), 757.97(m, C =S), 3302.42(s, hydroxide radical), 1166.83(s, C-O);

[0042] (2) Get 0.1 mmol of the ligand L3 obtained in step (1) to be dissolved in a volume ratio of V MeOH :V MeCN = In the mixed solvent of 6:2, add 0.1mmol Na[AuCl 4 ]·2H 2 O, stirred at room temperature for 4-6h, the product after the reaction was a gray-black pr...

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Abstract

The invention discloses a gold complex taking o-vanillin thiosemicarbazone as a ligand and a synthesis method thereof. During synthesis, thiosemicarbazone is dissolved in methanol, o-vanillin is added, reflux reaction and filtration are performed, filtrate is volatilized at room temperature, crystals are separated out, and the ligand is obtained after diethyl ether is used for washing and drying;the ligand is dissolved in methanol or methanol and acetonitrile, wherein the volume ratio of methanol to acetonitrile is 3:1; reflux reaction and filtering are performed to obtain a precipitate; theprecipitate is washed by ether, the washed precipitate is placed in an oven and dried; finally the precipitate is dissolved and filtered, the filtrate is placed on the bottom of a test tube, n-hexaneis paved on the upper layer, and crystals are obtained after several hours of diffusion, namely the gold complex. In-vitro proliferation inhibition activity experiments are carried out on the synthesized gold complex, and results show that the synthesized gold complex has generally better in-vitro activity than ligands of the synthesized gold complex, shows very good inhibition activity, has little toxic effect on human normal cells, and is suitable for preparing high-efficiency and low-toxicity anti-tumor drugs.

Description

technical field [0001] The invention relates to the synthesis of gold complexes, in particular to a gold complex with o-vanillin thiosemicarbazone as a ligand, a synthesis method and application thereof. Background technique [0002] Cancer is a disease caused by the control of cell growth and proliferation mechanism, and it is one of the most common diseases in the world. In the process of human cell metabolism, normal cells mainly replace aging cells with controlled division cells, but when normal cells are out of control due to certain diseases, cancer may occur. [0003] Cisplatin drugs have achieved great success in the clinical treatment of cancer, but they also have strong toxic side effects and cross-drug resistance defects. Considering that Au(Ⅲ) and Pt(Ⅱ) are isoelectronic bodies, and they both adopt a planar tetragonal configuration when coordinating, Au(Ⅲ) complexes have become a hot spot in the field of metallomedicine research. Thiosemicarbazone refers to a c...

Claims

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Application Information

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IPC IPC(8): C07F1/12A61P35/00
CPCA61P35/00C07F1/005
Inventor 杨峰楚永庞金惠贾晓颖杨通富邓勒
Owner GUANGXI NORMAL UNIV
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