Platinum complex using 2-amino-5-chlorobenzophenone thiosemicarbazone as ligand, and synthesis method and application thereof

A technology of chlorobenzophenone thiosemicarbazone and chlorobenzophenone, which is applied in the field of synthesis of metal complexes, can solve the problems of no anti-tumor activity, achieve novel structure, excellent neuroma inhibitory activity, and overcome drug The effect of drug resistance

Inactive Publication Date: 2019-04-30
GUANGXI NORMAL UNIV
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AI Technical Summary

Problems solved by technology

However, 2-amino-5-chlorobenzophenone had no appreciable antitumor activity

Method used

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  • Platinum complex using 2-amino-5-chlorobenzophenone thiosemicarbazone as ligand, and synthesis method and application thereof
  • Platinum complex using 2-amino-5-chlorobenzophenone thiosemicarbazone as ligand, and synthesis method and application thereof
  • Platinum complex using 2-amino-5-chlorobenzophenone thiosemicarbazone as ligand, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis method of C1 complex is:

[0029] 1) Dissolve 3mmol (693mg) 2-amino-5-chlorobenzophenone in 20mL ethanol, then add 3mmol (315mg) 4-methyl-3-thiosemicarbazide and mix well, add 3-4 drops of concentrated Sulfuric acid was refluxed and filtered, the filtrate was volatilized at room temperature, and light yellow crystals were precipitated, the crystals were filtered, and washed with absolute ethanol for 2-3 times to obtain compound 1;

[0030] Yield: 0.75g, 78.6%, light yellow solid; R f =0.414(Petroleum ether:EtOAc=1:1).M.p.133-135℃. 1 H NMR (400MHz, DMSO-d 6 )δ8.79(q,J=4.5Hz,1H),8.70(s,1H),7.72-7.69(m,2H),7.42-7.37(m,3H),7.29(dd,J=8.8,2.5Hz ,1H),6.92-6.90(m,2H),5.28(s,2H),3.06(d,J=4.6Hz,3H). 13 C NMR (100MHz, DMSO-d 6 )δ177.72, 145.97, 144.55, 135.86, 130.55, 129.54, 128.25, 127.55, 119.68, 117.44, 116.18, 31.30.ESI + m / z: calcd for C 15 h 16 ClN 4 S, 317 [M-H] + .

[0031] 2) Take 0.05mmol (15.9mg) of compound 1 and 23mg of Pt(DMSO) obtained in s...

Embodiment 2

[0034] The synthesis method of C2 complex is:

[0035] 1) Dissolve 3mmol (693mg) 2-amino-5-chlorobenzophenone in 20mL ethanol, then add 3mmol (543mg) 4-(2-methylphenyl)-3-thiosemicarbazide and mix well, drop Add 3-4 drops of concentrated sulfuric acid, reflux, and filter, the filtrate is volatilized at room temperature, and pale yellow crystals are precipitated, the crystals are filtered, and washed 2-3 times with absolute ethanol to obtain compound 2;

[0036] Yield: 0.71g, 60.0%, light yellow solid; R f =0.421 (Petroleum ether:EtOAc=2:

[0037] 1).M.p.140-142℃. 1 H NMR (400MHz, DMSO-d 6 )δ10.23(s,1H),9.04(s,1H),7.82-7.79(m,2H),7.43-7.37(m,3H),7.33-7.29(m,3H),7.25-7.22(m, 2H),6.99-6.93(m,2H),5.39(s,2H),2.27(s,3H). 13 C NMR (100MHz, DMSO-d 6)δ176.99,146.83,144.63,137.91,135.82,135.24,130.63,130.08,129.68,128.40,128.29,128.23,127.88,126.83,125.93,119.76,117.50,1176.7 + m / z: calcd for C 21 h 18 ClN 4 S, 393 [M-H] + .

[0038] 2) Take 0.05mmol (15.2mg) of compound 2 a...

Embodiment 3

[0041] The synthetic method of C3 complex is:

[0042] 1) Dissolve 3mmol (693mg) 2-amino-5-chlorobenzophenone in 20mL ethanol, then add 3mmol (273mg) thiosemicarbazide and mix well, add 3-4 drops of concentrated sulfuric acid, reflux, filter, and the filtrate Volatilize at room temperature, and a light yellow crystal precipitates out. The crystal is filtered and washed with absolute ethanol 2-3 times to obtain compound 3;

[0043] Yield: 0.76g, 83.3%, light yellow solid; R f =0.321(Petroleum ether:EtOAc=1:1).M.p.158-160℃. 1 H NMR (400MHz, DMSO-d 6 )δ8.61(s,2H),8.28(s,1H),7.72-7.69(m,2H),7.41-7.35(m,3H),7.28(dd,J=8.8,2.6Hz,1H),6.92 -6.90(m,2H),5.29(s,2H). 13 CNMR (100MHz, DMSO-d 6 )δ178.09, 146.40, 144.57, 135.80, 130.57, 129.60, 128.27, 127.63, 119.68, 117.45, 116.12.ESI + m / z: calcd for C 14 h 14 ClN 4 S, 303 [M-H] + .

[0044] 2) Take 0.05mmol (17.9mg) of compound 3 and 23mg of Pt(DMSO) obtained in step 1) 2 Cl 2 Place in a glass tube with one end sealed, add 2 ...

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Abstract

The invention discloses a platinum complex using 2-amino-5-chlorobenzophenone thiosemicarbazone as a ligand, and a synthesis method and an application thereof. The synthesis method of the platinum complex comprises the following steps: 1) dissolving 2-amino-5-chlorobenzophenone in ethanol, adding thiosemicarbazide, performing uniform mixing, adding 3-4 drops of concentrated sulfuric acid, refluxing the obtained solution, performing filtration, evaporating the obtained filtrate at room temperature to precipitate pale yellow crystals, filtering the obtained crystals, and washing the crystals with anhydrous ethanol 2-3 times to obtain a compound; and 2) placing the compound obtained in step 1) and Pt(DMSO)2Cl2 in a glass tube sealed at one end, dropwise adding methanol into the glass tube todissolve above two substances, carrying out vacuum sealing on the glass tube, and standing the glass tube in a 60 DEG C blast drying oven for 72 h to obtain the target complex. The complex has the advantages of novel structure, greatly improved activity, excellent anti-neuroma activity, facilitation of penetration of BBB, and overcoming of the drug resistance to a certain degree.

Description

technical field [0001] The invention relates to the synthesis of metal complexes, in particular to a platinum complex with 2-amino-5-chlorobenzophenone thiosemicarbazone as a ligand, a synthesis method and application thereof. Background technique [0002] The blood brain barrier (BBB) ​​is a dynamic interface separating the central nervous system from the circulatory system. It maintains homeostasis and normal nervous function by regulating the exchange of substances between the central nervous system and the circulatory system. According to research reports, less than 3% of central nervous system drugs can pass through the BBB to achieve therapeutic purposes, and most of them are small molecule drugs. Therefore, for drug research and development companies, the risk of developing new brain disease drugs is very high, which greatly limits the development of brain drugs. In particular, the treatment of brain tumors is still limited by the BBB. Compounds must pass through t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61P35/00
CPCA61P35/00C07F15/0086
Inventor 杨峰张琚政张振雷梁宏
Owner GUANGXI NORMAL UNIV
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