Indium complex taking APT as ligand and having potential leaving group as well as synthesis method and application of the indium complex

A kind of technology of leaving group and synthesis method, applied in the field of indium complex and its synthesis

Inactive Publication Date: 2019-11-22
GUANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few studies on the application of metal indium in anti-tumor

Method used

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  • Indium complex taking APT as ligand and having potential leaving group as well as synthesis method and application of the indium complex
  • Indium complex taking APT as ligand and having potential leaving group as well as synthesis method and application of the indium complex
  • Indium complex taking APT as ligand and having potential leaving group as well as synthesis method and application of the indium complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthetic method of C1 indium complex is:

[0029] 1) Dissolve 2-acetylpyridine (363mg, 3mmol) in a mixture of 10mL methanol and 10mL acetonitrile, add thiosemicarbazide (273mg, 3mmol), drop 3-4 drops (about 1mL) of acetic acid, and reflux at 85°C After 10h, the reaction was concentrated under reduced pressure, extracted with ethyl acetate, washed with saturated sodium bicarbonate and water successively, and the eluent was separated by silica gel column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate, petroleum ether and acetic acid The volume ratio of ethyl ester is 10:1) to obtain ligand L1 (0.525g, 90.2%, pale yellow solid);

[0030] Yield: 0.525g, 90.2%, C 8 h 10 N 4 S: C, 49.46; H, 5.19; N, 28.84; S, 16.51. Found: C, 49.41; H, 5.18; N, 28.90; (s,NH),3147(m,aromatichydrogen),1600(m),1512(s),1450(s,aromatic),1398(m,C=N),1291(s,thioamide),1156(s) ,1101(s),882(m,C-H),714(m,C=S),596(m). 1 H NMR (400MHz, DMSO-d 6 )δ10.32(s,1H),8.5...

Embodiment 2

[0034] The synthetic method of C2 indium complex is:

[0035] 1) Dissolve 2-acetylpyridine (363mg, 3mmol) in a mixture of 10mL methanol and 10mL acetonitrile, add 4-methylthiosemicarbazide (315mg, 3mmol), add dropwise 3-4 drops (about 1mL) of acetic acid , refluxed at 85° C. for 10 h, concentrated under reduced pressure at the end of the reaction, extracted with ethyl acetate, washed with saturated sodium bicarbonate and water successively, and separated by silica gel column chromatography eluent (the eluent was a mixture of petroleum ether and ethyl acetate, petroleum The volume ratio of ether and ethyl acetate is 10:1), to obtain ligand L2 (0.520g, 83.3%, pale yellow solid);

[0036] Yield: 0.520g, 83.3%, C 8 h 10 N 4S: C, 51.90; H, 5.81; N, 26.90; S, 15.39. Found: C, 51.87; H, 5.80; N, 26.92; (s,NH),3143(m,aromatichydrogen),1599(m),1511(s),1450(s,aromatic),1388(m,C=N),1293(s,thioamide),1157(s) ,1101(s),883(m,C-H),715(m,C=S),594(m). 1 H NMR (400MHz, DMSO-d 6 )δ10.34(s...

Embodiment 3

[0040] 1) Dissolve 2-acetylpyridine (363mg, 3mmol) in a mixture of 10mL methanol and 10mL acetonitrile, add 4,4-dimethylthiosemicarbazide (357mg, 3mmol), drop 3-4 drops (approx. 1mL) acetic acid, reflux at 85°C for 10h, concentrate under reduced pressure after the reaction, extract with ethyl acetate, wash with saturated sodium bicarbonate and water successively, and separate the eluent from silica gel column chromatography (the eluent is petroleum ether and ethyl acetate) The mixture, the volume ratio of petroleum ether and ethyl acetate is 10:1), to obtain ligand L3 (0.531g, 79.72%, pale yellow solid);

[0041] Yield: 0.531g, 79.72%, C 10 h 14 N 4 S: C, 54.03; H, 6.35; N, 25.20; S, 14.42. Found: C, 54.01; H, 6.36; N, 25.21; (s,NH),3155(m,aromatichydrogen),1596(m),1503(s),1458(s,aromatic),1397(m,C=N),1292(s,thioamide),1154(s) ,1105(s),883(m,C-H),714(m,C=S),593(m). 1 H NMR (400MHz, DMSO-d 6 )δ8.71(dd, J=5.5,1.3Hz,1H),8.28(td,J=7.8,1.7Hz,1H),8.09(d,J=8.1Hz,1H),7.81–7.78(m...

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Abstract

The invention discloses an indium complex taking APT as a ligand and having a potential leaving group as well as a synthesis method and application of the indium complex. The synthesis method comprises the following steps: dissolving 2-acetylpyridine in a mixed solution of methanol and acetonitrile, adding aminothiourea, uniformly mixing the mixture, dropwise adding acetic acid, uniformly mixing the mixture, refluxing the mixed solution, performing vacuum concentration to obtain a concentrate, extracting the concentrate with ethyl acetate, washing a product with saturated sodium bicarbonate and water in order after the extraction step, and carrying out silica gel column chromatography separation to obtain a ligand; adding the ligand obtained in the step 1) and INCl3 into a closed reactionkettle, dropwise adding a mixed solution of methanol and ethanol for dissolving, sealing the reaction kettle after dissolving, and standing the reaction kettle in a vacuum drying oven at 65-80 DEG C for 72 hours to obtain the indium complex. The complex shows good inhibition activity on a cisplatin drug-resistant strain, new data is provided for application of the novel metal-based complex to drug-resistant tumor cell strains, and the synthesis method is simple to operate and convenient to implement.

Description

technical field [0001] The invention relates to the synthesis of indium complexes, in particular to an indium complex with APT as a ligand and a potential leaving group, its synthesis method and application. Background technique [0002] The applicability of thiosemicarbazide as an antineoplastic drug has been studied for more than half a century. Rosenberg found that cisplatin (cis-[PtCl 2 (NH 3 ) 2 ]) have good anti-tumor activity, the introduction of metal ions into thiosemicarbazide ligands has become an important research direction for the study of new anti-cancer metal-based drugs. Due to the serious drug resistance of platinum-based metal compounds, it is imminent to develop new anti-cancer metal-based compounds that have no cross-resistance to cisplatin. As a novel thiosemicarbazide ligand, the Schiff base formed by (2-acetylpyridine) APT and thiosemicarbazide exhibited good antitumor activity, and its main mechanism was to inhibit the activity of nucleoside reduc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/00A61P35/00A61K31/555
CPCA61P35/00C07F5/003
Inventor 杨峰李艳萍张琚政梁宏
Owner GUANGXI NORMAL UNIV
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