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2H-pyrazole sulfanilamide C21 steroid sapogenin derivative as well as preparation method and application thereof

A solid product and reaction technology, applied in the field of dihydropyrazole sulfonamide C21 steroidal saponin aglycon derivatives, can solve the problems of in-depth research and achieve the effects of mild experimental environment, good yield and good stability

Inactive Publication Date: 2015-09-02
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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  • 2H-pyrazole sulfanilamide C21 steroid sapogenin derivative as well as preparation method and application thereof
  • 2H-pyrazole sulfanilamide C21 steroid sapogenin derivative as well as preparation method and application thereof
  • 2H-pyrazole sulfanilamide C21 steroid sapogenin derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A

[0043] A Novel Dihydropyrazole Sulfonamide C 21 The synthetic method of steroidal saponin aglycon derivative, it has following general formula:

[0044]

[0045] Concretely consists of the following steps:

[0046] Step 1. Under stirring at room temperature, add Tenacissoside A 1 (a kind of C 21 steroidal saponins), hydrochloric acid aqueous solution, absolute ethanol, after stirring for 1 h, the reaction flask was transferred to an oil bath, and the reaction was refluxed for 7-9 h. TLC tracking reaction (developing agent V AcOEt :V PE =1:2), after the reaction was finished, filter, and the obtained solid was washed successively with dilute hydrochloric acid (3×100mL), distilled water (3×150mL), cold ethanol (3×50mL), distilled water (3×100mL), and dried. The obtained solid crude product was dissolved in absolute ethanol and recrystallized to obtain partially reduced crystalline C 21 Steroidal Saponin Aglycone 2.

[0047] Step 2. Under the action of stirring in an ice...

Embodiment 1

[0052] 4-(-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxyl)-(10a,12a-dimethyl)-(1,2-cyclo Preparation of pentyl)-1,10a-b-epoxyn-tetradecyl)-(4,5-dihydropyrazole))benzenesulfonamide (compound 10)

[0053]

[0054] Under stirring at -20°C, add the corresponding intermediate 8 (10.0mmol) and dichloromethane (25mL) obtained in step 4 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 10 was obtained as crystals.

[0055] White crystals were obtained with a yield of 63.6%. m.p.186~187℃; 1 H NMR (DMSO-d 6...

Embodiment 2

[0057] 4-(5-methyl-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)-(10a,12a-dimethyl)-(1 ,2-cyclopentyl)-1,10a-b-epoxy tetradecyl)-(4,5-dihydropyrazole))benzenesulfonamide (compound 11)

[0058]

[0059] The preparation method refers to Example 1.

[0060] White crystals were obtained with a yield of 78.6%. m.p.193~194℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:8.00(d,J=8.0Hz,2H,ArH),7.78(d,J=7.5Hz,2H,ArH),6.89(s,2H,NH 2 ),5.37(s,2H,OH),4.49(s,1H,OH),3.58~3.33(m,3H,CH),2.75~2.71(m,1H,CH),2.38~2.30(m,2H, CH 2 ), 2.01(t, J=7.3Hz, 1H, CH), 1.79~1.21(m, 18H, CH, CH 2 and CH 3 ),1.14(dd,J 1 =7.1Hz,J 2 =7.8Hz, 1H, CH), 0.89(s, 3H, CH 3 ),0.83(s,3H,CH 3 ).ESI-MS:560.7[M+H] + .Anal.Calcd for C 29 h 41 N 3 o 6 .

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Abstract

The invention discloses a compound, a preparation method of the compound and an application of the compound to preparation of an antitumor drug. The structural formula of the compound is shown in the specification, wherein R1 is H, CH3 or CH2CH3. The compound has the advantages of better biological activity, higher selectivity, lower toxicity and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a dihydropyrazolesulfonamide C 21 Steroidal saponin aglycon derivatives, and preparation methods and applications thereof. 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00C07J75/00A61K31/635A61P35/00
CPCC07J71/001C07J75/00
Inventor 杨永安魏元刚金显友钟慧朱海亮
Owner JIANGSU NAIQUE BIOLOGICAL ENG
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