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

A technology of dihydropyrazole sulfonamide and saponin aglycone, which is applied in the direction of medical preparations containing active ingredients, steroids, drug combinations, etc., can solve the problems of in-depth research and achieve good repeatability, high selectivity, The effect of low toxicity

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

[0048] 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))benzenesulfonamide (Compound 32 ) preparation

[0049]

[0050] Under stirring at -20°C, add the corresponding intermediate 18 (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. 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.

[0051] White crystals were obtained with a yield of 56.7%. m.p.214~2...

Embodiment 2

[0052] 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 sulfonamide (compound 33)

[0053]

[0054] The preparation method is the same as in Example 1. White crystals were obtained with a yield of 55.4%. m.p.229~230℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:8.2(d,J=8.3Hz,2H,ArH),7.84~7.68(m,4H,ArH),7.56~7.45(m,2H,ArH),6.96(d,J=7.3Hz, 1H, ArH), 6.88 (d, J=5.1Hz, 2H, NH 2 ), 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:686.9[M+H] + .Anal.Calcd for C 39 h 47 N 3 o 6 S: C, H, N.

Embodiment 3

[0055] 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 sulfonamide (compound 34)

[0056]

[0057] 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:8.01~7.90(m,4H,ArH),7.75(d,J=6.1Hz,2H,ArH),7.43(t,J=7.4Hz,1H,ArH),7.10(d,J= 7.2Hz, 1H, ArH), 6.92(d, J=6.6Hz, 1H, ArH), 6.88(s, 2H, NH 2 ),5.37(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:686.9[M+H] + .Anal.Calcd for C 39 h 47 N 3 o 6 S: C, H, N.

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Abstract

The invention discloses a pyrazoline sulfanilamide C21 steroid saponin aglycone derivative containing a naphthalene skeleton, a preparation method of the derivative, and an application in preparing an anti-tumor drug. A structural formula of the derivative is as shown as Formula VI as shown in the specification, wherein R1 is selected from H or CH3; R2 is selected from H, CH3, CF2, Cl or Br; R3 is selected from H, CH3 or Br; and R4 is selected from H or CH3. The derivative has the advantages of better bioactivity, higher selectivity, lower toxicity and the like and 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 dihydropyrazolesulfonamide C containing a naphthalene ring skeleton 21 Steroidal saponin aglycone derivatives and their preparation methods and applications. 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, et...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61K31/58A61P35/00
CPCC07J43/003
Inventor 朱海亮严晓强杨永安俞海荣钟飞
Owner JIANGSU NAIQUE BIOLOGICAL ENG
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