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Eudistomins Y derivative with anti-tumor activity as well as preparation method and application of Eudistomins Y derivative

A technology of antineoplastic drugs and derivatives, applied in antineoplastic drugs, chemical instruments and methods, organic chemistry, etc., can solve the problems of individual differences in drug action and drug resistance, and achieve the effect of expanding the scope of drug use

Active Publication Date: 2020-07-17
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemotherapy is a common and effective means of tumor treatment in clinical practice. However, due to the adverse reactions of traditional drugs, individual differences in drug action and drug resistance, the design and development of innovative anti-tumor drugs has become a major challenge in the global drug market.

Method used

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  • Eudistomins Y derivative with anti-tumor activity as well as preparation method and application of Eudistomins Y derivative
  • Eudistomins Y derivative with anti-tumor activity as well as preparation method and application of Eudistomins Y derivative
  • Eudistomins Y derivative with anti-tumor activity as well as preparation method and application of Eudistomins Y derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040] Tryptamine (128mg, 0.8mmol), p-hydroxyacetophenone (96mg, 0.8mmol) and I 2 (162 mg, 0.64 mmol) was dissolved in DMSO (3 mL), and H was added at room temperature 2 o 2 (30%, 1.5eq), after stirring and dissolving, the temperature rose to 110°C, and TLC tracked and detected the reaction. After the reaction was completed, the reaction was cooled to room temperature, ethyl acetate, saturated brine, 10% Na 2 S 2 o 3 , saturated ammonium chloride, extracted, dried with anhydrous sodium sulfate, filtered, concentrated, separated and purified by column chromatography to obtain EudistominY1 (138mg, 0.48mmol, 60%) as a yellow solid.

[0041] Eudistomin Y1, 1 H NMR (400MHz, DMSO-d 6 )δ11.90(s,1H),8.48(d,J=5.0Hz,1H),8.36(d,J=4.9Hz,1H),8.27(d,J=7.9Hz,1H),8.22(ddd, 2H),7.75(d,J=8.2Hz,1H),7.55(ddd,J=8.3,7.1,1.2Hz,1H),7.25(td,1H),6.90(ddd,2H).

[0042]

[0043] Under argon protection, EudistominY1 (289mg, 1mmol) and K 2 CO 3 (690mg, 5mmol) was dissolved in anh...

Embodiment 2

[0047] Preparation of compound 3

[0048]

[0049] Under argon protection, compound 2 (30mg, 0.09mmol) and K 2 CO 3 (62mg, 0.45mmol) was dissolved in anhydrous DMF (1mL), and methyl iodide (28μL, 0.45mmol) was slowly added in an ice bath, stirred at room temperature, and the reaction was monitored by TLC. It was extracted with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and column chromatographed to obtain compound 3 (27mg, 0.08mmol, 90%) as a white solid.

[0050] Compound 3, 1 HNMR (400MHz, CDCl 3 )δ8.51(d,J=5.1Hz,1H),8.19(d,J=7.9Hz,1H),8.13–8.10(m,1H),8.09–8.04(m,2H),7.69–7.61(m ,1H),7.49(d,J=8.3Hz,1H),7.37–7.30(m,1H),7.09–7.04(m,2H),4.78(d,J=2.4Hz,2H),3.77(s, 3H),2.59–2.52(m,1H).

Embodiment 3

[0053]

[0054] Tryptamine (161mg, 1mmol), p-methoxyacetophenone (150mg, 1mmol) and I 2 (203 mg, 0.8 mmol) was dissolved in DMSO (4 mL), and H was added at room temperature 2 o 2 (30%, 1.5eq), stir to dissolve, raise the temperature to 120°C, and track and detect the reaction by TLC. After the reaction was completed, the reaction was cooled to room temperature, ethyl acetate, saturated brine, 10% Na 2 S 2 o 3 , saturated ammonium chloride, extracted, dried over anhydrous sodium sulfate, filtered, concentrated, separated and purified by column chromatography to obtain yellow solid compound 4 (151 mg, 0.5 mmol, 50%).

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Abstract

The invention discloses a Eudistomins Y derivative with anti-tumor activity as well as a preparation method and application of the Eudistomins Y derivative. A tryptamine derivative (i) is used as a raw material and is subjected to a feeding reaction with acetophenone derivatives (ii), I2 and H2O2 to obtain a compound represented by a general formula (iii), and the compound represented by the general formula (iii) is subjected to a feeding reaction with R-X and K2CO3 according to the molar ratio of 1:(2-6):(2-6) to obtain a compound represented by a general formula (I). The invention provides the Eudistomins Y derivative represented by a general formula (I) and a medically acceptable salt thereof. The Eudistomins Y derivative has the antitumor activity, and is obviously superior to an Eudistomin Y1 prototype compound in the aspect of inhibiting tumor cell proliferation; compared with the non-fluorescence activity of a natural Eudistomins Y compound, the Eudistomins Y derivative represented by the general formula (I) provided by the invention has a fluorescence characteristic and can effectively trace the distribution of the Eudistomins Y derivative in cells and tissues.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a new class of Eudistomins Y derivatives, a drug combination containing them, a preparation method thereof, and an application thereof in the field of antitumor. Background technique [0002] At present, the incidence of cancer is increasing year by year, and it has become one of the major diseases that threaten human health and even life. Chemotherapy is a common and effective means of tumor treatment in clinical practice. However, due to the adverse reactions of traditional drugs, individual differences in drug action and drug resistance, the design and development of innovative anti-tumor drugs has become a major challenge in the global drug market. [0003] Due to the complexity of the living environment of marine organisms and the diversity of species, the natural products extracted from them have many new structural skeletons, unique chemical struct...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61P35/00C09K11/06G01N21/64
CPCC07D471/04A61P35/00C09K11/06G01N21/6428G01N21/6402G01N21/6458C09K2211/1044G01N2021/6432Y02P20/55
Inventor 杨刚强王聪慧高洪艳章琛高萌任瑞银邹宗吉
Owner YANTAI UNIV
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