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Arenobufagin derivative, preparation method thereof, pharmaceutical composition of arenobufagin derivative and application ofarenobufagin derivative
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A technology of sandbuad toxin and its derivatives, which is applied in the field of medicine and can solve the problems of narrow therapeutic index and high toxicity
Active Publication Date: 2020-12-11
ANHUI CHINA RESOURCES JINCHAN PHARMA CO LTD
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[0007] Although sabugain has excellent anti-tumor activity, its toxicity is relatively high and the therapeutic index is relatively narrow. Therefore, it is necessary to carry out structural modification on this basis to enhance the activity of the compound and reduce toxicity, so as to discover new anti-tumor drugs.
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Embodiment 1
[0081] The preparation of embodiment 1 compound Ia
[0082]
[0083] Add sabubaptin (43mg, 0.1mmol), N-Boc-D-aminobutyric acid (101.6mg, 0.5mmol) and DMAP (48.8mg, 0.2mmol) into a 25mL flask, add 5mL di Chloromethane. Then EDCI (230mg, 1.2mmol) was added in batches, stirred overnight at room temperature, the solvent was evaporated, and 36.4mg of white solid was obtained by column chromatography with a yield of 46.3%. 1 H NMR (500MHz, CDCl 3 )δ:7.74(d,1H),7.35(s,1H),6.23(d,1H),5.39(s,1H),5.00–5.15(m,3H),3.99–4.36(m,3H),2.91 –3.02(m,1H),1.23–2.18(m,39H),0.83–1.10(m,12H).ESI-HRMS calcd C42H62N2O12[M+Na] + m / z, 809.4200; found 809.4206.
Embodiment 2
[0084] The preparation of embodiment 2 compound 1b
[0085]
[0086] Referring to the preparation method of compound Ia in Example 1, N-Boc-D-aminobutyric acid was replaced by N-Boc-D-aminobutyric acid to obtain a white solid with a yield of 44.3%. 1 H NMR (500MHz, CDCl 3 )δ:7.72(d,1H),7.38(s,1H),6.28(d,1H),5.43(d,1H),5.00–5.16(m,3H),4.03–4.32(m,3H),1.72 –2.28(m,12H),1.26–1.57(m,28H),1.15(s,3H),0.99(s,3H).ESI-HRMS calcd C40H58N2O12[M+Na] + m / z, 781.3887; found 781.3886.
Embodiment 3
[0087] The preparation of embodiment 3 compound Ic
[0088]
[0089] Referring to the preparation method of compound Ia in Example 1, N-Boc-D-aminobutyric acid was replaced by N-Boc-D-valine to obtain a white solid with a yield of 39.6%. 1 H NMR (500MHz, CDCl 3 )δ: 7.74(d,1H),7.38(s,1H),6.26(d,1H),5.38(d,1H),5.15(s,1H),4.96–5.05(m,2H),4.03–4.19 (m,3H),1.76–2.23(m,14H),1.26–1.51(m,24H),1.12(s,3H),1.03–1.07(m,6H),0.97–0.99(m,6H),0.89 (d,3H).ESI-HRMS calcd C44H66N2O12[M+Na] + m / z, 837.4513; found 837.4511.
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Abstract
The invention belongs to the technical field of medicine, and relates to an arenobufagin derivative, a preparation method thereof, a pharmaceutical composition of the arenobufagin derivative and application of the arenobufagin derivative. The arenobufagin derivative has antitumor activity; the pharmacological activity of the arenobufagin derivative enables the arenobufagin derivative to be used for preparing anti-tumor, cardiovascular and anti-nervous system drugs. The invention provides a lead compound for developing a new anti-tumor drug, and opens up a new way for deeply researching and developing the new anti-tumor drug.
Description
technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a class of sabuad toxin derivatives, a preparation method, a pharmaceutical composition and applications thereof. Background technique [0002] Arenobufagin is a bufolide compound extracted from toadvenom. Its chemical structure is as follows: [0003] [0004] Studies have shown that sabuad toxin has strong anti-tumor activity, can inhibit the adhesion, migration, invasion and angiogenesis of liver cancer HepG2 cells (Chinese Pharmacology Bulletin, 2011, 27; 19-23), and can also significantly inhibit liver cancer SMMC-7721 mitochondrial apoptosis pathway induces apoptosis of tumor cells (Chinese Medicine Emergency, 2013, 22: 1845-1883). Therefore, it is of great significance to synthesize sandbuad toxin derivatives, study their structure-activity relationship, and find sandbuad toxin derivatives with high efficiency and low toxicity. [0005] At present, there...
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