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C21 steroid saponin aglycone derivative as well as preparation method and application thereof in preparing anti-tumor drugs

A technology of saponin aglycone and derivatives, applied in the preparation of antitumor drugs, in the field of C21 steroidal saponin aglycone derivatives, can solve problems such as lack of in-depth research, and achieve a mild experimental environment, high selectivity, and good biological active 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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  • C21 steroid saponin aglycone derivative as well as preparation method and application thereof in preparing anti-tumor drugs
  • C21 steroid saponin aglycone derivative as well as preparation method and application thereof in preparing anti-tumor drugs
  • C21 steroid saponin aglycone derivative as well as preparation method and application thereof in preparing anti-tumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] N-methyl-4-(5-phenyl-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)-(10a,12a-dimethyl base)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole))benzoylpiperazine (compound 22) preparation of

[0065]

[0066] Under stirring at -20°C, add the corresponding intermediate 18 (10.0mmol) and dichloromethane (25mL) obtained in step 7 to a 50mL round bottom flask in turn, and gradually add boron tribromide (5.0mmol) dropwise and continue stirring After reacting for 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 vacuum, the obtained solid was dissolved in absolute ethanol, purified by recrystallization, and the target compound 22 was obtained as crystals.

[0067] White crystals were obtained with a yield of 47.3%. m.p.221~223℃; ...

Embodiment 2

[0069] N-methyl-4-(5-(4-fluoro-phenyl)-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxyl)-( 10a,12a-Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole))benzoyl Preparation of piperazine (compound 23)

[0070]

[0071] The preparation method refers to Example 1. White crystals were obtained with a yield of 45.5%. m.p.226~227℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:8.03(d,J=8.3Hz,2H,ArH),7.73(d,J=8.1Hz,2H,ArH),7.35~7.18(m,4H,ArH),5.35(s,2H, OH), 5.19(t, J=7.1Hz, 1H, CH), 4.49(s, 1H, OH), 3.56~3.41(m, 6H, CH and CH 2 ), 3.32(d, J=6.8Hz, 1H, CH), 2.97~2.71(m, 2H, CH 2 ), 2.28(t, J=7.7Hz, 4H, CH 2 ),2.15(s,3H,CH 3 ), 2.04(t, J=5.7Hz, 1H, CH), 1.81~1.20(m, 15H, CHand CH 2 ),1.14(dd,J 1 =7.0Hz,J 2 =7.6Hz,1H,CH),0.89(s,3H,CH 3 ),0.78(s,3H,CH 3 ).ESI-MS:687.9[M+H] + .Anal.Calcd for C 40 h 51 FN 4 o 5 :C,H,N.

Embodiment 3

[0073] N-methyl-4-(5-(2-fluoro-phenyl)-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxyl)-( 10a,12a-Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole))benzoyl Preparation of piperazine (compound 24).

[0074]

[0075] The preparation method refers to Example 1. White crystals were obtained with a yield of 44.9%. m.p.212~213℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:10.56(s,1H,OH),8.03(d,J=8.1Hz,2H,ArH),7.74~7.55(m,5H,ArH and NH),7.29~7.23(m,1H,ArH ),7.15~7.07(m,1H,ArH),5.37(s,2H,OH),5.19(t,J=7.3Hz,1H,CH),4.48(s,1H,OH),3.55~3.42(m ,6H,CH and CH 2 ), 3.34(d, J=6.8Hz, 1H, CH), 2.95~2.73(m, 2H, CH 2 ), 2.32(t, J=7.7Hz, 4H, CH 2 ), 2.01(t, J=5.4Hz, 1H, CH), 1.79~1.21(m, 15H, CH and CH 2 ),1.14(dd,J 1 =7.1Hz,J 2 =7.9Hz,1H,CH),0.84(s,3H,CH 3 ),0.81(s,3H,CH 3 ).ESI-MS:687.9[M+H] + .Anal.Calcd for C 40 h 51 FN 4 o 5 :C,H,N.

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Abstract

The invention discloses a C21 steroid saponin aglycone derivative as well as a preparation method and an application thereof in preparing anti-tumor drugs. The structural formula of the C21 steroid saponin aglycone derivative is as shown in formula IX. The C21 steroid saponin aglycone derivative disclosed by the invention has the advantages of being better in bioactivity, higher in selectivity, lower in toxicity and the like. The C21 steroid saponin aglycone derivative has a significant inhibitory effect on human breast cancer cells, cervical cancer cells, lung cancer cells and liver cancer cells (as shown in Specification), wherein R1 is selected from H and F, R2 is selected from H and F, and R3 is selected from H and F.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, especially a C 21 Steroidal saponin aglycone derivative, its preparation method and its application in the preparation of antitumor drugs. Background technique [0002] Steroidal saponins can be obtained through extraction, separation and purification from the traditional Chinese medicine Tongguanteng. The 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 inhibitor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61P35/00
CPCC07J71/001
Inventor 严晓强朱海亮杨永安钟飞俞海荣
Owner JIANGSU NAIQUE BIOLOGICAL ENG
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