A kind of tetravalent platinum polyamine complex, its preparation method and application

A technology of complexes and tetravalent platinum, applied in platinum-based organic compounds, platinum-group organic compounds, chemical instruments and methods, etc., to improve bioavailability, enhance the effect on innate and acquired drug-resistant cells, and improve stability Effect

Active Publication Date: 2020-05-29
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Existing studies have found that 65%-98% of platinum-based drugs are excreted from the body after being combined with various proteins, especially sulfur-containing proteins (glutathione GSH and metallothionein, etc.). Platinum finally combines with DNA to play an anti-tumor effect, which largely limits the amount of active platinum

Method used

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  • A kind of tetravalent platinum polyamine complex, its preparation method and application
  • A kind of tetravalent platinum polyamine complex, its preparation method and application
  • A kind of tetravalent platinum polyamine complex, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Example 1: 5f 1

[0079]

[0080] 1 H NMR (300MHz,MeOD)δ=3.36–2.91(m,13H),2.88–2.04(m,6H),1.56(d,J=28.0,5H),1.42(d,J=7.2,28H),1.26 (m,19H),0.94(t,J=34.0,3H). 13 C NMR (300MHz,MeOD)δ=175.08,174.30,164.74,158.27,157.17,80.47,80.10,55.67,40.87,40.39,40.08,37.00,32.95,30.71,30.37,28.77,28.18,247.51,267.51, .

[0081] Its preparation method is as follows:

[0082]

[0083]The preparation method is as follows: oxidize the divalent platinum compound cisplatin Cis. with hydrogen peroxide at 60-70°C and react for 4 hours to prepare the tetravalent cisplatin compound Oxide-Cis.; the tetravalent cisplatin compound Oxide-Cis. -Cis. (1equiv) and palmitic anhydride (4equiv) were dissolved in DMF, reacted overnight at 70°C under nitrogen protection, and then the oil pump was pumped dry. After adding dichloromethane to precipitate a solid, the compound Cis could be prepared by washing with chloroform, ether, etc. (IV)-COOH; DMF solution of Cis(IV)-COOH and 2-(7-azobenzotria...

Embodiment 2

[0084] Example 2: 5b 1

[0085]

[0086] 1 H NMR (300MHz,MeOD)δ=3.22–3.00(m,14H),2.61–2.44(m,2H),2.36(d,J=7.0,2H),2.24(t,J=7.5,2H),1.56 (m,8H),1.36(s,27H),1.29–1.12(m,24H),1.00(t,J=7.0,3H),0.79(t,J=6.5,3H). 13 C NMR (300MHz, MeOD) δ=175.19, 174.37, 157.15, 151.31, 80.92, 80.89, 80.71, 55.75, 46.25, 46.19, 45.82, 37.01, 34.93, 33.03, 32.73, 30.78, 30.730, 30.63, 535, 3 ,30.20,28.83,26.97,26.05,23.70,19.32,14.51,13.21.

Embodiment 3

[0087] Example 3: 5c 1

[0088]

[0089] 1 H NMR (300MHz,MeOD)δ=3.35–3.16(m,2H),3.09(d,J=11.2,11H),2.63–2.42(m,2H),2.35(d,J=7.5,2H),2.23 (s,2H),1.96–1.40(m,8H),1.35(s,27H),1.28–0.87(m,22H),0.78(t,J=6.1,3H). 13 C NMR (300MHz, MeOD) δ=175.19, 174.36, 157.16, 156.55, 81.57, 80.94, 73.18, 46.24, 46.04, 45.81, 37.99, 37.01, 33.02, 32.73, 32.50, 30.76, 30.62, 30.439, 3 ,28.83,26.97,25.99,23.69,19.34,14.51.

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Abstract

The invention belongs to the technical field of pharmaceutical chemistry, in particular to tetravalent platinum polyamine complexes, a preparation method and application thereof. The aim of the invention is to provide a tetravalent platinum antitumor drug modified by a polyamine with high stability and high targeting and the preparation method thereof so as to overcome shortcomings existing in theprior art. The synthesized compounds have good antitumor activity, the anti-tumor activity is better than that of cisplatin and oxaliplatin, and the stability is better than that of bivalent platinumsuch as cisplatin, carboplatin, oxaliplatin and the like. The cancer cell targeting of the polyamine modified tetravalent platinum is relatively good, and the high selectivity of cancer cells is improved. The compounds solve the existing problems that divalent platinum antitumor drugs have poor solubility and complicated clinical compatibility, and the compounds have relatively good liposolubility and water solubility.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a tetravalent platinum polyamine complex, its preparation method and application. Background technique [0002] In recent years, tetravalent platinum-based antineoplastic drugs as prodrugs of divalent platinum-based drugs have become the focus of research and development of platinum-based drugs. The tetravalent platinum center platinum ion belongs to d 6 electron configuration, in d 2 sp 3 The hybridized orbitals are bonded to form a stable inner orbital complex, which not only retains the broad-spectrum and high-efficiency anti-tumor properties of divalent platinum-based drugs, but also has high stability, less accumulation in the body, low toxicity and side effects, and targeted Strong, no cross-resistance, etc., and the characteristics of easy modification of tetravalent platinum axial ligands provide more possibilities for the research diversity of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61P35/00
CPCA61P35/00C07F15/0093Y02P20/55
Inventor 马静谢松强王超杰刘瀚方
Owner HENAN UNIVERSITY
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