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Sapogenin derivative, preparation method of derivative and application thereof in preparation of antitumor drugs

A technology for saponin aglycone and derivatives, which is applied to saponin aglycone derivatives, its preparation, and the application field in the preparation of anti-tumor drugs, can solve problems such as lack of in-depth research, and achieves mild experimental environment, simple required conditions, and high performance. selective effect

Active Publication Date: 2015-04-29
JIANGSU NAIQUE BIOLOGICAL ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently for such C 21 The research on steroidal saponins is still not in-depth, mainly based on their physical and chemical properties, separation, purification, analysis and detection research, structural modification research on its mother nucleus, and pharmacological activity research on its structural characteristics

Method used

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  • Sapogenin derivative, preparation method of derivative and application thereof in preparation of antitumor drugs
  • Sapogenin derivative, preparation method of derivative and application thereof in preparation of antitumor drugs
  • Sapogenin derivative, preparation method of derivative and application thereof in preparation of antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] 4-(5-(1,3-Benzodioxane)-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)-(10a,12a- Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole))benzoylhydroxamic acid ( Compound 33) Preparation

[0057]

[0058] Under stirring at -20°C, add the corresponding intermediate 27 (10.0mmol) and dichloromethane (25mL) obtained in step 7 to a 50mL round bottom flask in turn, and gradually add boron tribromide (5mmol) dropwise to continue the reaction with stirring After 1 h, the reaction flask was transferred to room temperature, and the reaction was continued for 12 h. TLC tracking reaction (developing agent V AcOEt :V 正己烷 =1:2), after the reaction was completed, filtered, the solid was washed with distilled water, and finally dried in vacuo, and the obtained solid was dissolved in absolute ethanol for recrystallization and purification to obtain the crystalline target compound.

[0059] White crystals were obtained with a yield of 54.5%. m.p.233~234℃...

Embodiment 2

[0061] 4-(5-(4-methyl-1,3-benzodioxane)-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)- (10a,12a-Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole))Benzene Preparation of Acylhydroxamic Acid (Compound 34)

[0062]

[0063] The preparation method refers to Example 1. White crystals were obtained with a yield of 42.6%. m.p.222~224℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:10.47(s,1H,OH),8.00(d,J=7.5Hz,2H,ArH),7.76(d,J=7.5Hz,2H,ArH),7.72(s,1H,NH) ,5.91(d,J=4.7Hz,1H,ArH),5.78~5.62(m,2H,ArH),5.50(s,1H,CH 2 ),5.40(dd,J 1 =11.3Hz,J 2 =11.1Hz,1H,CH 2 ), 5.39(s, 2H, OH), 4.48(s, 1H, OH), 4.16(d, J=10.1Hz, 1H, CH), 3.53~3.29(m, 5H, CH and CH 2 ),2.24~2.15(m,2H,CH 2 ), 2.01(t, J=4.5Hz, 1H, CH), 1.80~1.10(m, 18H, CH and CH 2 ),0.88(s,3H,CH 3 ),0.84(s,3H,CH 3 ).ESI-MS:662.8[M+H] + .Anal.Calcd for C 37 h 47 N 3 o 8 :C,H,N.

Embodiment 3

[0065] 4-(5-(7-Methyl-1,3-benzodioxane)-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)- (10a,12a-Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole))Benzene Preparation of Acyhydroxamic Acid (Compound 35)

[0066]

[0067] The preparation method refers to Example 1. White crystals were obtained with a yield of 45.4%. m.p.215~216℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:10.52(s,1H,OH),7.95(d,J=7.2Hz,2H,ArH),7.75(d,J=6.8Hz,2H,ArH),7.45(s,1H,NH) ,5.97(d,J=4.7Hz,1H,ArH),5.82~5.61(m,2H,ArH),5.40(s,1H,CH 2 ),5.36(dd,J 1 =11.8Hz,J 2 =11.4Hz,1H,CH 2), 5.32(s, 2H, OH), 4.59(s, 1H, OH), 4.13(d, J=10.3Hz, 1H, CH), 3.58~3.29(m, 5H, CH and CH 2 ),2.28~2.15(m,2H,CH 2 ), 2.01(t, J=4.8Hz, 1H, CH), 1.87~1.16(m, 18H, CH and CH 2 ),0.89(s,3H,CH 3 ),0.78(s,3H,CH 3 ).ESI-MS:662.8[M+H] + .Anal.Calcd for C 37 h 47 N 3 o 8 :C,H,N.

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Abstract

The invention discloses a sapogenin derivative shown as a structural formula IX, a preparation method of the sapogenin derivative, and application thereof in preparation of antitumor drugs. The structural formula is as shown in the specification, wherein R1 is selected from H and CH3; R2 is selected from H and CH3; and n refers to 1 and 2. The sapogenin derivative disclosed by the invention has the advantages of high biological activity, high selectivity, low toxicity and the like and has obvious effects of inhibiting human breast cancer cells, cervical cancer cells, lung carcinoma cells and hepatoma carcinoma cells.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a saponin aglycone derivative, its preparation method and its application in the preparation of antitumor drugs. Background technique [0002] The steroidal saponins obtained by extracting, separating and purifying from the traditional Chinese medicine Tongguanteng, its aglycone is a unique steroidal saponin structure composed of 21 C atoms, so it is called C 21 steroidal saponins. Existing studies have shown that with C 21 Steroidal saponin core compounds have pharmacological activities such as immunoregulation and anti-asthma, and have been widely used clinically as the index active ingredients of drugs. [0003] The inventor finds through research: have C 21 The compound of steroidal saponin core has good antitumor activity, and has good inhibitory effect on various tumors, such as liver cancer, lung cancer, esophageal cancer, etc., has good inhibitory activity. Currentl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61K31/58A61P35/00
CPCC07J71/001
Inventor 杨永安朱海亮严晓强俞海荣钟飞
Owner JIANGSU NAIQUE BIOLOGICAL ENG
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