Synthesis of 9-chloro-1,2,3,4-tetrahydroacridine-platinum (II) complex targeted to liver cancer and application of the complex

A technology of tetrahydroacridine and complexes, applied in the field of medicine, can solve the problem of not conducting clinical experiments, etc., and achieve the effects of superior in vitro antitumor activity, good medicinal value, and good in vitro antitumor activity

Active Publication Date: 2018-03-02
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although compounds or drugs that inhibit the proliferation of liver cancer cells can be well discovered, these discoveries are only used in the study of anti-tumor activity in vitro, and almost no clinical trials have been carried out; therefore, it is urgent to design a series of low-toxicity, high-efficiency drugs targeting liver cancer. Active and targeted new anti-tumor drugs (including inorganic metal anti-tumor complexes)
[0004] On the other hand, 9-chloro-1,2,3,4-tetrahydroacridine is used as the upstream raw material of the clinical drug tacrine, and its parent ring structure has good aromatic planarity, which is an excellent organic ligand However, it has not yet been seen that 9-chloro-1,2,3,4-tetrahydroacridine and dichloro two (dimethyl sulfoxide) platinum (II) carry out coordination reaction to obtain dichloro two Related reports on the synthesis and application of methylsulfoxide·9-chloro-1,2,3,4-tetrahydroacridinium platinum(II)

Method used

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  • Synthesis of 9-chloro-1,2,3,4-tetrahydroacridine-platinum (II) complex targeted to liver cancer and application of the complex
  • Synthesis of 9-chloro-1,2,3,4-tetrahydroacridine-platinum (II) complex targeted to liver cancer and application of the complex
  • Synthesis of 9-chloro-1,2,3,4-tetrahydroacridine-platinum (II) complex targeted to liver cancer and application of the complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Weigh 1.0mmol cis-PtCl 2 (DMSO) 2 Dissolve in 10mL of water; heat and dissolve 1.0mmol of Ligand L in 30mL of methanol, mix and react the two solutions, and reflux at 65°C for 12 hours. After the reaction, the yellow target product (yellow crystal) is obtained, cooled, After filtering, the obtained yellow solid was washed with water, methanol and ether in sequence, and dried to finally obtain a yellow solid product (yield 98.5%).

[0041] Identify the resulting yellow blocky crystals:

[0042] (1) Infrared spectrum, its spectrogram is as follows Figure 4 shown.

[0043] IR(KBr):3924,3777,3439,3005,2924,2871,1616,1567,1487,1452,1408,1369,1307,1146,1024,968,920,868,825,765,693,635,591,501,440cm -1 .

[0044] (2) X-ray single crystal diffraction spectrum, its spectrogram is as follows Figure 5 shown.

[0045] (3) Elemental analysis results are shown in Table 1 above.

[0046] Therefore, it can be determined that the obtained yellow blocky crystals are the target ...

Embodiment 2

[0049] Weigh 3.0mmol cis-PtCl 2 (DMSO) 2 Dissolve in 5mL of dimethyl sulfoxide; heat and dissolve 1.0mmol of ligand L in 100mL of acetonitrile, mix and react the two solutions, and reflux at 90°C for 48 hours to obtain the yellow target product (yellow crystal), cooled, filtered, washed and filtered yellow solid with water, methanol, and ether in turn, and dried to finally obtain a yellow solid product (yield 85.0%).

Embodiment 3

[0051] Weigh 0.5mmol cis-PtCl 2 (DMSO) 2 Dissolve in 20mL of acetone; heat and dissolve 1.0mmol of ligand L in 60mL of ethanol, mix and react the two solutions, and reflux at 45°C for 28 hours. After the reaction, the yellow target product (yellow crystal) is obtained, and cooled , filtered, and the yellow solid obtained by washing and filtering with water, methanol, and ether successively was dried to finally obtain a yellow solid product (yield 87.1%)

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Abstract

The invention discloses synthesis of a 9-chloro-1,2,3,4-tetrahydroacridine-platinum (II) complex targeted to liver cancer and an application of the complex and belongs to the technical field of medicines. The invention aims to provide a dichloro-dimethyl-sulfoxide-9-chloro-1,2,3,4-tetrahydroacridine-platinum (II) complex having a novel structure, and a synthesis method and an application thereof.The chemical structure formula of the dichloro-dimethyl-sulfoxide-9-chloro-1,2,3,4-tetrahydroacridine-platinum (II) complex is represented as follow. The complex can be used for producing antitumor medicines.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to the synthesis and application of a 9-chloro-1,2,3,4-tetrahydroacridine-platinum (II) complex targeting liver cancer. Background technique [0002] Since the 1970s, cisplatin has been widely used clinically to treat various malignant tumors such as testicular cancer, cervical cancer, bladder cancer, ovarian cancer, head and neck cancer, and small cell or non-small cell lung cancer. One of the most effective and commonly used drugs for tumors (Rosenberg, B.; et al. Nature, 1965, 205:698-699.), but serious adverse reactions in normal tissues often limit its clinical application, and the adverse reactions of cisplatin have Ototoxicity, gastrointestinal toxicity, myelosuppression, allergy and nephrotoxicity (Liang H.; et al. Eur. J. Med. Chem., 2015, 92:302-313.). Therefore, it is imminent to develop new platinum-based anti-tumor chemotherapy drugs with high efficiency, low toxicity...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61P35/00
CPCC07F15/0093
Inventor 覃其品谭明雄王书龙罗旭健
Owner YULIN NORMAL UNIVERSITY
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