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

A dihydropyrazole sulfonamide and saponin aglycone technology, which is applied in the field of dihydropyrazole sulfonamide C21 steroidal saponin aglycon derivatives, can solve problems such as easy drug resistance, limited application range, and reduced use range. To achieve the effect of novel structure, low toxicity and short residual effect

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

However, this type of medicine is a bacteriostatic agent without bactericidal effect, and it is easy to produce drug resistance and often use many adverse reactions, so its application range is greatly limited.
And because it is easy to produce drug resistance, the scope of use has been gradually reduced

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] 4-(5-(2-thiophene)-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)-(10a,12a-dimethyl) Preparation of -(1,2-cyclopentyl)-1,10a-b-epoxyn-tetradecyl)-(4,5-dihydropyrazole))benzenesulfonamide (compound 22)

[0044]

[0045] Under stirring at -20°C, add the corresponding intermediate 13 (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.

[0046] White crystals were obtained with a yield of 43.9%. m.p.194~195℃; 1...

Embodiment 2

[0048] 4-(5-(2-(5-methyl-thiophene))-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)-(10a ,12a-Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxy n-tetradecyl)-(4,5-dihydropyrazole))benzenesulfonamide ( Compound 23) Preparation

[0049]

[0050] White crystals were obtained with a yield of 43.9%. m.p.198~199℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:8.01(d,J=7.9Hz,2H,ArH),7.73(d,J=7.3Hz,2H,ArH),6.89(s,2H,NH 2 ), 6.80(d, J=6.7Hz, 1H, CH), 6.55(d, J=5.8Hz, 1H, CH), 5.34(s, 2H, OH), 4.55(s, 1H, OH), 3.88( t,J=6.6Hz,1H,CH),3.54(dd,J 1 =4.7,J 2 =4.8Hz,1H,CH),3.44(t,J=8.1Hz,1H,CH),3.34(d,J=6.8Hz,1H,CH),2.79(dd,J 1 =3.7,J 2 =3.4Hz,2H,CH 2 ),2.37(s,3H,CH 3 ), 2.01(t, J=7.1Hz, 1H, CH), 1.85~1.23(m, 15H, CH and CH 2 ),1.14(dd,J 1 =7.2Hz,J 2 =7.1Hz,1H,CH),0.89(s,3H,CH 3 ),0.84(s,3H,CH 3 ).ESI-MS:642.8[M+H] + .Anal.Calcd for C 33 h 43 N 3 o 6 S 2 :C,H,N.

Embodiment 3

[0052] 4-(5-(2-(5-fluoro-thiophene))-3-((3aR,4aS,8S,10aS,11S,12S,12aS)-(8,11,12-trihydroxy)-(10a, 12a-Dimethyl)-(1,2-cyclopentyl)-1,10a-b-epoxy-n-tetradecyl)-(4,5-dihydropyrazole))benzenesulfonamide (compound 24) Preparation

[0053]

[0054] The preparation method is the same as in Example 1. White crystals were obtained with a yield of 56.2%. m.p.218~219℃; 1 H NMR (DMSO-d 6 ,300MHz)δ:8.04(d,J=6.5Hz,2H,ArH),7.70(d,J=7.4Hz,2H,ArH),6.89(s,2H,NH 2 ), 6.46(d, J=6.7Hz, 1H, CH), 5.32(s, 2H, OH), 5.19(t, J=7.3Hz, 1H, CH), 4.35(s, 1H, OH), 3.82( t,J=5.3Hz,1H,CH),3.54(dd,J 1 =4.7,J 2 =4.8Hz,1H,CH),3.44(t,J=8.1Hz,1H,CH),3.34(d,J=6.8Hz,1H,CH),2.79(dd,J 1 =3.7,J 2 =3.4Hz,2H,CH 2 ), 2.01(t, J=7.4Hz, 1H, CH), 1.76~1.13(m, 15H, CH and CH 2 ),1.11(dd,J 1 =6.7Hz,J 2 =7.3Hz,1H,CH),0.89(s,3H,CH 3 ),0.84(s,3H,CH 3 ).ESI-MS:646.8[M+H] + .Anal.Calcd for C 32 h 40 FN 3 o 6 S 2 :C,H,N.

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Abstract

The invention discloses a pyrazoline sulfanilamide C21 steride saponin aglycone derivative containing a thiophene skeleton, as well as a preparation method and an application of the derivative. The derivative takes a compound with a C21 steroid saponin mother nucleusas a starting compound, a structural modification research is carried out on the compound to form a compound as shown as the following formula as shown in the specification, R1 is H, CH3, F, Cl or Br, and R2 is H, CH3, F, Cl or Br. A pharmacological research shows that the compound 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 drug synthesis, in particular to a dihydropyrazolesulfonamide C containing a thiophene skeleton 21 Steroidal saponin aglycon derivatives, and preparation methods and applications thereof. Background technique [0002] Thiophenes are sulfur-containing heterocyclic compounds that are widely distributed in many species of the Asteraceas family (Asteraceae), including many species with known medicinal uses. Natural thiophene compounds are believed to play an important role in phytochemical defense against herbivorous insects and other pests. Natural thiophenes have been described to have cytotoxic activity upon exposure to long-wave ultraviolet light. Photochemical studies have shown that the phototoxicity of thiophene is mainly due to the generation of toxic single oxygen through a type II photodynamic process. [0003] Sulfonamides have a variety of biological activities and have been studied in the field of medic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61P35/00
CPCC07J71/001C07J75/00
Inventor 魏元刚严晓强金显友钟慧杨永安
Owner JIANGSU NAIQUE BIOLOGICAL ENG
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