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Isosteviol amide derivatives and preparation method therefor

A technology for isosteviol amide and its derivatives, which is applied in the field of isosteviol amide derivatives and its preparation, can solve problems such as rare reports, and achieve simple preparation methods, good application prospects, and high yields Effect

Active Publication Date: 2020-01-03
ZHENGZHOU INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the amide structural unit exhibits such a broad spectrum of activities, there are few reports on the introduction of amide substructural units into the molecular backbone of isosteviol.

Method used

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  • Isosteviol amide derivatives and preparation method therefor
  • Isosteviol amide derivatives and preparation method therefor
  • Isosteviol amide derivatives and preparation method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] General method for the preparation of embodiment 1 compound I-1~I-3, II-9

[0039] Compounds 4, 8, 12, 14 (10 mmol) and propionic anhydride (11 mmol) were weighed and dissolved in 100 mL of pyridine solution, and the reaction was stirred at room temperature until the reaction was detected by TLC. A large amount of distilled water was added to the system, a white solid was precipitated, filtered, washed with water until neutral to obtain the crude compound, and recrystallized from ethanol to obtain the corresponding white solid compounds I-1~I-3 and II-9.

[0040]Among them, compounds 4, 8, 12, and 14 (refer to the paper European Journal of Medicinal Chemistry 115 (2016) 26-40 for synthetic conditions).

[0041]

[0042] Compound I-1: Yield: 89%; 1 H NMR (400MHz, CDCl 3, ppm): δ5.51(d, J=8.6Hz, 1H), 4.12–4.00(m, 2H), 2.22(q, J=7.6Hz, 2H), 2.16(d, J=13.3Hz, 1H), 1.91–1.77(m,3H),1.70–1.54(m,6H),1.40–1.29(m,5H),1.24(t,J=7.1Hz,3H), 1.16(t,J=7.6Hz,3H) ,1.15(s,3H),1.10–...

Embodiment 2

[0046] General method for the preparation of embodiment 2 compound I-4 and I-5

[0047] Compounds 8 and 12 (10 mmol) and propionic anhydride (22 mmol) were weighed and dissolved in 100 mL of pyridine solution, stirred at room temperature for reaction, and detected by TLC until the reaction was complete. A large amount of distilled water was added to the system, a white solid was precipitated, filtered, and the solid was washed with water until neutral to obtain the crude compound, which was recrystallized from ethanol to obtain the corresponding white solid compounds I-4 and I-5.

[0048] Compound I-4: Yield: 97%; 1 H NMR (400MHz, CDCl 3 ,ppm): δ5.41(d,J=9.8Hz,1H),4.28(dd,J=10.9,5.7Hz,1H),4.13–4.04(m,3H),3.95(dd,J=9.8,6.0 Hz,1H),2.33–2.27(m,2H),2.23–2.14(m,3H),2.05–2.01(m,1H),1.87–1.67(m,6H),1.57(d,J=11.6Hz, 2H),144–1.29(m,2H),1.25(t,J=7.1Hz,3H),1.16(t,J=8.0Hz,3H),1.15(s,3H),1.12(t,J=7.7 Hz,3H),1.08–0.90(m,6H),0.88(s,3H),0.76(s,3H); 13 C NMR (100MHz, CDCl 3 , ppm): δ177....

Embodiment 3

[0050] General method for the preparation of embodiment 3 compound I-6~I-8, II-10

[0051]Weigh compounds 4, 8, 12, 14 (10mmol) and dissolve them in 100mL of dichloromethane, add 1mL of acid-binding agent DIPEA and benzoyl chloride (1.6g, 11mmol) respectively, stir and react at room temperature for 2 hours, detect by TLC, and react complete. After the solvent was evaporated under reduced pressure, ethyl acetate and saturated brine were added for extraction, the organic phase was washed three times with saturated brine, the organic phase was dried with anhydrous sodium sulfate, filtered, concentrated, fried, and separated by column chromatography to obtain the corresponding White solid compounds I-6 to I-8 and II-10.

[0052]

[0053] Compound I-6: Yield: 92%; 1 H NMR (400MHz, CDCl 3 , ppm): δ7.75(d, J=7.0Hz, 2H), 7.50(t, J=7.3Hz, 1H), 7.44(t, J=7.2Hz, 1H), 6.10(d, J=8.4Hz ,1H), 4.26–4.20(m,1H),4.13–3.99(m,2H),2.16(d,J=13.2Hz,1H),2.00(dd,J=14.1, 11.6Hz,1H),1.84– 1.59(m,...

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Abstract

The invention provides isosteviol amide derivatives represented by structural formulae I-IV shown in the description and pharmaceutically acceptable salts thereof. Amide fragment containing novel isosteviol derivatives are synthesized through introducing an amide substructure unit to a molecular skeleton of isosteviol, carrying out structural modification by 16-position carbonyl and 19-position carboxyl of the isosteviol, and carrying out D-ring ring opening and ring enlargement reactions. Another object of the invention is to provide a synthesis method for the compounds and an application ofthe compounds in the aspect of antitumor performance.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to isosteviolamide derivatives and a preparation method thereof. Background technique [0002] Cancer has seriously threatened human health, and its mortality rate is second only to cardiovascular and cerebrovascular diseases, ranking second in the world. At present, cancer treatment methods mainly include radiotherapy, surgery and drug therapy, among which drug therapy is still the most important method for treating cancer. Therefore, the development of new anticancer drugs with high efficiency and low toxicity has become the focus of research and development, and significant progress has been made. With the continuous deepening of the research and development of new anticancer drugs, anticancer active ingredients with low toxicity and high curative effect are found from animals and plants, and further structural modifications are carried out on the active ingredient...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/52C07C233/81C07C233/58C07D221/22C07C233/61C07C231/02C07C231/24A61P35/00
CPCC07C233/52C07C233/81C07C233/58C07D221/22C07C233/61C07C231/02C07C231/24A61P35/00C07C2603/86
Inventor 刘从军卢奎李靖靖刘彦平闵玉涛姜巧娟李玉玲王保玉
Owner ZHENGZHOU INST OF TECH
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