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Furan skeleton-containing dihydropyrazolsulfanilamide C21 steroid sapogenin derivative, and preparation method and application thereof

A technology of dihydropyrazole sulfonamide and saponin aglycone, applied in the direction of medical preparations containing active ingredients, steroids, drug combinations, etc., can solve the problems of high toxicity, low biological activity and selectivity, and achieve low toxicity , good biological activity, novel structure effect

Inactive Publication Date: 2015-08-12
JIANGSU NAIQUE BIOLOGICAL ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the existing products still have disadvantages such as low biological activity and selectivity, and high toxicity.

Method used

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  • Furan skeleton-containing dihydropyrazolsulfanilamide C21 steroid sapogenin derivative, and preparation method and application thereof
  • Furan skeleton-containing dihydropyrazolsulfanilamide C21 steroid sapogenin derivative, and preparation method and application thereof
  • Furan skeleton-containing dihydropyrazolsulfanilamide C21 steroid sapogenin derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: 4-(5-(2-furan)-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)-(10a,12a- Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole))benzenesulfonamide (Compound 10) preparation of

[0048]

[0049] Under stirring at -20°C, add the corresponding intermediate 7 (10.0mmol) and dichloromethane (25mL) obtained in step 4 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. The reaction was tracked by TLC (developer VAcOEt:V n-hexane=1:2). After the reaction, it was filtered, the solid was washed with distilled water, and finally dried in vacuum. The obtained solid was dissolved in absolute ethanol for recrystallization and purification to obtain the crystalline target compound.

[0050] White crystals were obtained with a yield of 48.9%. m.p.196~197℃; 1H N...

Embodiment 2

[0051] Example 2: 4-(5-(2-(5-methyl-furan))-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy )-(10a,12a-dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxytetradecyl)-(4,5-dihydropyrazole)) Preparation of Benzenesulfonamide (Compound 11)

[0052]

[0053] The preparation method is the same as in Example 1 (using furan-2-carbaldehyde with different substituents from Example 1). White crystals were obtained with a yield of 44.2%. m.p.200~201℃; 1H NMR(DMSO-d6,300MHz)δ:8.03(d,J=7.5Hz,2H,ArH),7.73(d,J=7.6Hz,2H,ArH),6.88(s,2H ,NH2),6.17(d,J=5.2Hz,1H,CH),6.02(d,J=5.6Hz,1H,CH),5.58(t,J=4.4Hz,1H,CH),5.39(s, 2H, OH), 4.48(s, 1H, OH), 3.54(dd, J1=4.7, J2=4.2Hz, 1H, CH), 3.44(t, J=8.1Hz, 1H, CH), 3.34(d, J=6.8Hz, 1H, CH), 2.79(dd, J1=4.8, J2=5.1Hz, 2H, CH2), 2.20(s, 3H, CH3), 2.01(t, J=7.1Hz, 1H, CH) ,1.72~1.31(m,15H,CH and CH2),1.13(dd,J1=7.2Hz,J2=7.1Hz,1H,CH),0.84(s,3H,CH3),0.80(s,3H,CH3) .ESI-MS:626.8[M+H]+.Anal.Calcd for C33H43N3O7S:C,H,N.

Embodiment 3

[0054] Example 3: 4-(5-(2-(5-fluoro-furan))-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))benzene Preparation of sulfonamide (compound 12)

[0055]

[0056] The preparation method is the same as in Example 1 (using furan-2-carbaldehyde with different substituents from Example 1). White crystals were obtained with a yield of 53.1%. m.p.215~216℃; 1H NMR (DMSO-d6, 300MHz) δ: 7.94(d, J=7.1Hz, 2H, ArH), 7.77(d, J=7.9Hz, 2H, ArH), 7.68(d, J =5.1Hz,1H,CH),6.87(s,2H,NH2),6.50(t,J=5.5Hz,1H,CH),5.58(t,J=5.3Hz,1H,CH),5.34(s, 2H, OH), 4.44(s, 1H, OH), 3.58(dd, J1=4.5, J2=4.1Hz, 1H, CH), 3.44(t, J=8.1Hz, 1H, CH), 3.34(d, J=6.8Hz, 1H, CH), 2.79(dd, J1=3.7, J2=3.4Hz, 2H, CH2), 2.01(t, J=7.1Hz, 1H, CH), 1.79~1.21(m, 15H, CH2 and CH), 1.14(dd, J1=7.2Hz, J2=7.1Hz, 1H, CH), 0.89(s, 3H, CH3), 0.84(s, 3H, CH3). ESI-MS: 630.7[M+ H]+.Anal.Calcd for C32H40FN3O7S:C,H,N.

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Abstract

The invention discloses a furan skeleton-containing dihydropyrazolsulfanilamide C21 steroid sapogenin derivative, and a preparation method and an application thereof. The structure of the furan skeleton-containing dihydropyrazolsulfanilamide C21 steroid sapogenin derivative is represented by formula VII shown in the specification; and in the formula VII, R1 is selected from H and CH3, and R2 is selected from H and F. The derivative has an obvious inhibition effect on human breast cancer cells (MCF-7), cervical carcinoma cells (HeLa), lung cancer cells (A549) and liver cancer cells (HepG2), has same or better cytotoxicity on human renal epithelial cells (293T) than positive control drug Celecoxib, and can be used to prepare antitumor drugs.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to dihydropyrazolesulfonamide C containing a furan skeleton 21 Steroidal saponin aglycone derivative, its preparation method and application. Background technique [0002] C21 steroidal saponin is a steroidal saponin component obtained through extraction, separation and purification from the traditional Chinese medicine Tongguanteng. Its aglycone is a unique steroidal saponin structure composed of 21 C atoms, so it is called C21 steroidal saponin. Compounds with a C21 steroidal saponin core have pharmacological activities such as immune regulation and antiasthma, and have been widely used clinically as index active ingredients of drugs. [0003] After in-depth research by the applicant, it is found that the compound with C21 steroidal saponin core may have good anti-tumor activity. The current research content on this type of C21 steroidal saponins mainly includes: separation, p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61K31/58A61P35/00
CPCC07J71/0021
Inventor 杨永安魏元刚金显友钟慧朱海亮
Owner JIANGSU NAIQUE BIOLOGICAL ENG
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