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Pregnane alkaloid derivative with effect of resisting breast cancer metastasis and medical application of pregnane alkaloid derivative

A technology of alkaloid derivatives and pregnane, which is applied in the field of medicinal chemistry research and can solve problems such as toxic and side effects

Inactive Publication Date: 2015-07-01
TIANJIN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the limitations of the curative effect and toxic and side effects of the current anti-tumor metastases chemotherapeutic drugs

Method used

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  • Pregnane alkaloid derivative with effect of resisting breast cancer metastasis and medical application of pregnane alkaloid derivative
  • Pregnane alkaloid derivative with effect of resisting breast cancer metastasis and medical application of pregnane alkaloid derivative
  • Pregnane alkaloid derivative with effect of resisting breast cancer metastasis and medical application of pregnane alkaloid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The synthetic method of compound 1 and 2

[0043] Weigh 4 equivalents of potassium tert-butoxide and 4 equivalents of ethyltriphenylphosphine bromide into a reaction flask, add an appropriate amount of anhydrous THF, and stir at room temperature for 1 hour. Add 1 equivalent of epiandrosterone or androsterone to the reaction solution, reflux under nitrogen protection, and TLC monitors that the reaction is complete. Add saturated ammonium chloride aqueous solution to terminate the reaction, extract with dichloromethane, wash with water three times, combine the organic phases, dry over anhydrous magnesium sulfate, filter, and concentrate to obtain a crude product. The crude product was recrystallized from dichloromethane-methanol to obtain pure product.

[0044] Synthesis of (Z)-3β-hydroxypregna-17(20)-ene(1)

[0045]

[0046] Using epiandrosterone as a raw material, it was prepared according to the above method, and the crude product was recrystallized from methanol ...

Embodiment 2

[0051] The synthetic method of compound 3 and 4

[0052] Weigh 1.13 equivalents of triphenylphosphine, 1.1 equivalents of phthalimide and 1 equivalent of compound 1 or 2 in a reaction flask, add an appropriate amount of anhydrous tetrahydrofuran and stir for 1 hour under an ice bath. Add 2 equivalents of diisopropyl azodicarboxylate to the reaction solution, stir at room temperature under seal, and monitor by TLC until the reaction is complete. Add water to quench the reaction, concentrate under reduced pressure to remove THF, extract with dichloromethane, wash with water three times, combine organic phases, dry over anhydrous magnesium sulfate, filter, and concentrate to obtain a crude product. The crude product was recrystallized to obtain pure product.

[0053] Synthesis of (Z)-3β-phthalimidopregna-17(20)-ene(3)

[0054]

[0055] Using 9.66 g of compound 2 as a raw material, it was prepared according to the above method, and the crude product was recrystallized from a ...

Embodiment 3

[0060] The synthetic method of compound 5,6,11 and 12

[0061] Weigh 1 equivalent of raw materials into a reaction flask, add an appropriate amount of methanol and 40 equivalents of 80% hydrazine hydrate to reflux. TLC monitored the end of the reaction. Cool to room temperature, add an appropriate amount of sodium hydroxide aqueous solution (4-6mol / L) until the solution turns white and turbid. Filtrate with suction, wash with water, and dry to obtain a crude product, which is purified by HW-40 gel column chromatography to obtain a pure product.

[0062] Synthesis of (Z)-3β-aminopregna-17(20)-ene(5)

[0063]

[0064] Using compound 3 as raw material, it was prepared according to the above method, and the crude product was purified by HW-40 gel column chromatography (DCM:MeOH=2:1, V / V) to obtain a white solid with a yield of 68.3%. 1 H NMR (400MHz, CDCl 3 )δ5.10(qt, J=2.0, 6.8Hz, 1H), 2.67(br s, 1H), 1.64(dt, J=2.0, 6.8Hz, 3H), 0.86(s, 3H), 0.79(s, 3H). 13 C NMR (100MHz...

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Abstract

The invention provides a pregnane alkaloid derivative with an effect of resisting breast cancer cell metastasis or a pharmaceutically acceptable salt thereof. The structure of the pregnane alkaloid derivative is shown by a general formula I in the specification, wherein R1 and R2 are independently selected from hydrogen, straight-chain or branched alkyl with the carbon atom number of 1-8, naphthenic base, unsaturated alkyl, benzyl and benzene ring substituted benzyl respectively; or R1R2N is piperidyl or pyrrolyl; R3 and R4 are independently selected from hydrogen and hydroxyl respectively; or R3R4 together represents carbonyl oxygen atoms; R5 and R6 are different substituting groups and are independently selected from hydrogen or methyl respectively; and the pharmaceutically acceptable salt is a salt formed with inorganic acid or organic acid, wherein the inorganic acid or organic acid is selected from hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methane sulfonic acid, benzene methane sulfonic acid, oxalic acid, tartaric acid, maleic acid, citric acid or ascorbic acid. The invention also provides an application of the pregnane alkaloid derivative in preparation of a medicament for resisting breast cancer metastasis.

Description

technical field [0001] The invention relates to a pregnane alkaloid derivative, a preparation method and its application as an anti-tumor breast cancer metastasis drug, which belongs to the field of medicinal chemistry research. Background technique [0002] In recent years, the incidence of tumor has been increasing, and it has become the number one killer that endangers people's health. Tumor metastasis is the main obstacle in tumor treatment. According to incomplete statistics, about 60% of clinically diagnosed tumor patients have metastasized. Tumor has become one of the major diseases that seriously threaten human health today. With the advancement of life sciences and the development of medicine, human beings' understanding of tumors has penetrated to the molecular and cellular level, and various new surgical treatment methods and chemotherapy drugs are constantly coming out. However, according to statistics from the American Institute of Cancer Research, over the pa...

Claims

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Application Information

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IPC IPC(8): C07J41/00C07J43/00A61K31/56A61K31/58A61P35/04
CPCC07J41/0005C07J41/0011C07J43/003
Inventor 段宏泉秦楠靳美娜寿晓媛甘椿椿刘倩
Owner TIANJIN MEDICAL UNIV
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