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Pyrazoline hydroxamic acid C21 steroid saponin aglycone derivative containing naphthalene skeleton, as well as preparation method and application of derivative

A technology of dihydropyrazole hydroxamic acid and saponin aglycone is applied in the field of dihydropyrazole hydroxamic acid C21 steroidal saponin aglycone derivatives and their preparation, which can solve the problems of insufficient research and achieve high selectivity , low toxicity, good biological activity

Inactive Publication Date: 2015-07-29
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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  • Pyrazoline hydroxamic acid C21 steroid saponin aglycone derivative containing naphthalene skeleton, as well as preparation method and application of derivative
  • Pyrazoline hydroxamic acid C21 steroid saponin aglycone derivative containing naphthalene skeleton, as well as preparation method and application of derivative
  • Pyrazoline hydroxamic acid C21 steroid saponin aglycone derivative containing naphthalene skeleton, as well as preparation method and application of derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: 4-(5-(α-naphthyl)-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))benzoylhydroxamic acid (Compound 36) Preparation

[0057]

[0058] Under stirring at -20°C, add the corresponding intermediate 26 (10.0mmol) and dichloromethane (25mL) obtained in step 6 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 51.2%. m.p.20...

Embodiment 2

[0060] Example 2: 4-(5-(5-methyl-α-naphthyl)-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 Formylhydroxamic Acid (Compound 37)

[0061]

[0062] The preparation method is the same as in Example 1. White crystals were obtained with a yield of 53.7%. m.p.212~213℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:10.50(s,1H,OH),8.2(d,J=8.3Hz,2H,ArH),7.84~7.68(m,5H,ArH and NH),7.56~7.45(m,2H,ArH ), 6.96(d, J=7.3Hz, 1H, ArH), 6.86(s, 1H, ArH), 5.37(s, 2H, OH), 5.18(t, J=7.4Hz, 1H, CH), 4.45( s,1H,OH),3.54(dd,J 1 =4.6,J 2 =4.7Hz, 1H, CH), 3.43(t, J=7.8Hz, 1H, CH), 3.34(d, J=6.9Hz, 1H, CH), 3.28~3.15(m, 2H, CH 2 ),2.62(s,3H,CH 3 ), 2.01(t, J=7.4Hz, 1H, CH), 1.75~1.21(m, 15H, CH and CH 2 ),1.10(dd,J 1 =6.4Hz,J 2 =6.1Hz,1H,CH),0.88(s,3H,CH 3 ),0.82(s,3H,CH 3 ).ESI-MS:666.8[M+H] + .Anal.Calcd for C 40 h 47 N 3 o 6 :C,H,N.

Embodiment 3

[0063] Example 3: 4-(5-(6-methyl-α-naphthyl)-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 Formylhydroxamic Acid (Compound 38)

[0064]

[0065] The preparation method is the same as in Example 1. White crystals were obtained with a yield of 52.3%. m.p.252~254℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:10.49(s,1H,OH),8.01~7.90(m,4H,ArH),7.75(d,J=6.1Hz,2H,ArH),7.64(s,1H,NH),7.43( t,J=7.4Hz,1H,ArH),7.10(d,J=7.2Hz,1H,ArH),6.92(d,J=6.6Hz,1H,ArH),5.42(s,2H,OH),5.16 (t,J=7.5Hz,1H,CH),4.48(s,1H,OH),3.55(dd,J 1 =4.6,J 2 =4.6Hz, 1H, CH), 3.41(t, J=7.8Hz, 1H, CH), 3.35(d, J=6.6Hz, 1H, CH), 3.27~3.15(m, 2H, CH 2 ),2.66(s,3H,CH 3 ), 2.01(t, J=7.1Hz, 1H, CH), 1.79~1.21(m, 15H, CH and CH 2 ),1.11(dd,J 1 =6.8Hz,J 2 =7.1Hz,1H,CH),0.88(s,3H,CH 3),0.81(s,3H,CH 3 ).ESI-MS:666.8[M+H] + .Anal.Calcd for C 40 h 47 N 3 o 6 :C,H,N.

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Abstract

The invention discloses a pyrazoline hydroxamic acid C21 steroid saponin aglycone derivative containing a naphthalene skeleton, a preparation method of the derivative and an application of the derivative in preparing an anti-tumor drug. The C21 steroid saponin aglycone derivative has a structural formula as shown as Formula IX as shown in the specification, wherein R1 is selected from H or CH3; R2 is selected from H or CH3; R3 is selected from H or CH3; and R4 is selected from H or CH3. The derivative has the advantages of better bioactivity, higher selectivity, lower toxicity and the like. The derivative has an obvious inhibiting effect on human breast cancer cells, cervical cancer cells, lung cancer cells and liver cancer cells.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to dihydropyrazole hydroxamic acid C containing a naphthalene ring skeleton 21 Steroidal saponin aglycone derivatives and their preparation methods and applications. 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, esoph...

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 严晓强朱海亮杨永安钟飞俞海荣
Owner JIANGSU NAIQUE BIOLOGICAL ENG
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