A novel rhein-platinum (iv) precursor anticancer complex and its synthesis method and application
A technology of complexes and acids, applied in the direction of active ingredients of platinum-based organic compounds, platinum-group organic compounds, and heavy metal compounds, which can solve problems affecting long-term clinical use and curative effect, low bioavailability, and easy drug resistance , to achieve good medicinal value, simple synthetic route, and good antitumor effect
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Embodiment 1
[0039] Weigh 2.0 mmol of benzoic acid (BA-COOH) and 1.0 mmol of cisplatin oxyhydroxide, put them in a 100 mL round-bottomed flask, dissolve them in 50.0 mL of acetic acid, protect from light, and carry out a coordination reaction at 37 °C for 12 h. After drying (45°C), the yellow target product Pt-1 was obtained. The yield was 35.6%.
[0040] The obtained yellow product Pt-1 was identified:
[0041] (1) Electrospray mass spectrometry, the spectrum is as follows figure 1 shown.
[0042] ESI-MS m / z:647.0for[M-Cl+DMSO+2CH 3 OH] + , where M is the molecular weight of compound Pt-1.
[0043] (2) H NMR spectrum, such as figure 2 shown.
[0044] 1 H NMR (500MHz, DMSO-d 6 )δ7.95(d,J=8.3Hz,4H),7.62(t,J=7.4Hz,2H),7.50(t,J=7.7Hz,4H),1.92(s,6H).
[0045](3) C NMR spectrum, such as image 3 shown.
[0046] 13 C NMR (126MHz, DMSO-d 6 )δ178.73,172.45,167.85,133.20,131.49,129.72,128.98,23.35,21.52.
[0047] (4) The infrared spectrum data of the complex Pt-1 are shown below.
...
Embodiment 2
[0055] Weigh 2.0 mmol of ferulic acid (FA-COOH) and 1.0 mmol of cisplatin oxyhydroxide, put them in a 100 mL round-bottomed flask, and dissolve them in 30.0 mL of a mixed solution of acetic acid and methanol (v:v=10:1) , protected from light, carried out the coordination reaction at 80°C for 90h, and dried (45°C) to obtain the yellow target product Pt-2. The yield was 55.7%.
[0056] The obtained yellow product Pt-2 was identified:
[0057] (1) Electrospray mass spectrometry, the spectrum is as follows Figure 4 shown.
[0058] ESI-MS m / z: 647.6 for [M-Cl] + , where M is the molecular weight of compound Pt-2.
[0059] (2) H NMR spectrum, such as Figure 5 shown.
[0060] 1 H NMR (500MHz, DMSO-d 6 )δ9.78(s, 2H), 7.48(d, J=15.8Hz, 2H), 7.28(s, 2H), 7.08(d, J=7.6Hz, 2H), 6.80(d, J=7.9Hz, 2H), 6.37(d, J=15.9Hz, 2H), 3.82(s, 6H), 1.91(s, 6H).
[0061] (3) C NMR spectrum, such as Image 6 shown.
[0062] 13 C NMR (126MHz, DMSO-d 6 )δ178.74,168.52,149.55,148.40,144.80,1...
Embodiment 3
[0069] Weigh 2.0 mmol of rhein (RH-COOH) and 1.0 mmol of cisplatin oxyhydroxide, put them in a 100 mL round-bottomed flask, and dissolve them in 85.0 mL of a mixed solution of acetic acid and dimethyl sulfoxide (v:v=100 : 3), protected from light, carried out the coordination reaction at 120°C for 72h, and dried (45°C) to obtain the yellow target product Pt-3. The yield was 50.1%.
[0070] The obtained yellow product Pt-3 was identified:
[0071] (1) Electrospray mass spectrometry, the spectrum is as follows Figure 7 shown.
[0072] ESI-MS m / z:696.4for[M-(OC-RH)+3CH 3 OH] - , where M is the molecular weight of the compound Pt-3.
[0073] (2) H NMR spectrum, such as Figure 8 shown.
[0074] 1 H NMR (500MHz, DMSO-d 6 )δ11.90(s,2H),8.16–8.09(m,1H),7.83(td,J=7.9,2.9Hz,1H),7.78–7.68(m,2H),7.40(dd,J=8.2, 3.2Hz, 1H), 6.54(s, 6H).
[0075] (3) C NMR spectrum, such as Figure 9 shown.
[0076] 13 C NMR (126MHz, DMSO-d 6 ) Δ191.81,178.69,172.51,165.98,161.91,161.59,138....
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