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Application of (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide in medicament pharmacy

A kind of chloropyridine, piperonyl technology, applied in (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbonyl The application field of hydrazine in pharmaceuticals has the effect of inhibiting the formation of microtubules and having good development and application prospects.

Inactive Publication Date: 2015-06-10
SHANDONG UNIV QILU HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the introduction of the acylhydrazone chemical structure pyrazoles form the newly synthesized (E)-N-piperonyl-1-(3-(6-chloropyridyl)methyl)-3-phenyl-

Method used

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  • Application of (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide in medicament pharmacy
  • Application of (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide in medicament pharmacy
  • Application of (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide in medicament pharmacy

Examples

Experimental program
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Example Embodiment

[0034] Example 1:

[0035] (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide

[0036] 1) Add potassium carbonate (0.005 mol), 3-phenyl-1H-pyrazole-5-ethyl carboxylate (0.005 mol), 2-chloro-5-chloromethylpyridine (0.005 mol) to a 100 ml round bottom flask Mol) and acetonitrile (25 ml), the device reflux condenser, the upper part is connected to the drying tube. Heat to reflux for 4 hours, react until the raw materials are completely consumed, and detect the end of the reaction by TLC. Concentrate under reduced pressure, remove the solvent, add ethyl acetate (30 ml), filter, and concentrate the filtrate. Use ethyl acetate-petroleum ether (V / V=1 / 2) as the eluent to separate the residue (100~ 200 mesh silica gel) to obtain 1-(3-(6-chloropyridine)methyl)-3-phenylpyrazole-5-carboxylic acid ethyl ester with a yield of 87%.

[0037] 2) To 0.341 g (0.001 mole) of 1-(3-(6-chloropyridine)methyl)-3-phenylpyrazole-5-carboxylic acid ethyl ester in methanol (5 ...

Example Embodiment

[0051] Example 2:

[0052] Determination of (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide on the half-inhibitory concentration of rhabdomyosarcoma cell growth by SRB method

[0053] At 37°C and 5% CO 2 Under the environment, human rhabdomyosarcoma RD cells were cultured with DMEM / 10% fetal bovine serum medium. Collect logarithmic phase human rhabdomyosarcoma RD cells, inoculate them in 96-well plates, and incubate for 24h. Add (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H at different concentrations (20, 10, 5, 1, 0.1, 0.05, 0.01μM) -Pyrazole-5-carbohydrazide was incubated for 48h, 50μL of trichloroacetic acid solution (30%) was added and fixed at 4°C for one hour. Shake off the solution, rinse with high-purity water five times, add 100 μL of sulforhodamine B to stain for 30 minutes after drying, and rinse with 1% acetic acid solution five times after spin-drying. After drying, add 100μL of Tris solution to fully dissolve, and ...

Example Embodiment

[0055] Example 3:

[0056] PI staining flow cytometry determination of (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide on rhabdomyosarcoma cells Cycle impact

[0057] Human rhabdomyosarcoma RD cells in the logarithmic growth phase were inoculated into 6 cm petri dishes at an amount of 200,000 cells per 3 mL of medium volume, and a total of 8 petri dishes were inoculated. After 24 hours, the 8 petri dishes were equally divided into two groups. DMSO was added to two petri dishes of each group, and 5.0 μM compound (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl- was added to two petri dishes. 1H-pyrazole-5-carbohydrazide. After continuously incubating for 24 hours, the cells were digested on ice, the cell suspension was collected, centrifuged and washed twice with PBS. Add 10 ml of 70% ice ethanol and suspend it at -20°C overnight. The cell suspension was centrifuged, washed twice with PBS, 500μL PI / 5μL RNAaseA was added to the cells a...

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Abstract

The invention discloses an application of a compound (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide in preparation of medicaments for resisting rhabdomyosarcoma. Experiments prove that the compound with a size of 0.80mu m can arouse a 50% growth inhibition effect of RD cells of human rhabdomyosarcoma, and the compound with a size of 5.0mu m can cause the cell cycle arrest and apoptosis-inducing of RD cells of human rhabdomyosarcoma, and through the investigation of action targets, the compound acts on tubulin so as to inhibit the formation of microtubules, therefore, the compound has a good development and application prospect in preparing medicaments for resisting rhabdomyosarcoma, and is expected to become an effective medicament for the treatment of rhabdomyosarcoma.

Description

technical field [0001] The present invention relates to the use of (E)-N-piperonyl-1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazole-5-carbohydrazide in the preparation of anti-rhabdomyosarcoma drugs application. Background technique [0002] Rhabdomyosarcoma (rhabdomyosarcoma) is a malignant tumor that occurs from embryonic mesenchymal tissue. Its incidence rate is second to malignant fibrous histiocytoma and liposarcoma, ranking third among soft tissue sarcomas. Rhabdomyosarcoma treatment mainly includes surgery, chemotherapy, radiation therapy, magnetic induction therapy and so on. Chemotherapy is an essential treatment in the treatment of cancer. Currently commonly used chemotherapeutic drugs are mainly vincristine, dactinomycin and cyclophosphamide, and new drugs include ifosfamide, etoposide and topotecan. But in use, because chemotherapy drugs kill some normal cells, it can cause many side effects, such as hair loss, nausea and vomiting, loss of appetite, fatigue...

Claims

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Application Information

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IPC IPC(8): A61K31/4439A61P35/00
Inventor 邵梅英刘德山高伟张艳霞
Owner SHANDONG UNIV QILU HOSPITAL
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