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Applicationof A-nor-5 alpha-androstane compounds in preparation of malignant tumor resistant medicaments

A technology for malignant tumors and compounds, applied in anti-tumor drugs, steroids, drug combinations, etc., can solve problems such as toxic effects, lack of selective tumor inhibition, damage, etc., achieve low drug toxicity, inhibit the growth of malignant tumor cells, good treatment effect

Active Publication Date: 2012-09-26
SHANGHAI AO QI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the antineoplastic drugs currently used lack the effect of selectively inhibiting tumors. While inhibiting the growth and development of malignant tumors, they also have significant effects on normal cells in the body, especially the proliferating bone marrow cells, intestinal mucosal epithelial cells, and germ cells. It also has a certain toxic effect on the important organs of the body: liver, kidney, heart, lung, nervous system, etc.

Method used

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  • Applicationof A-nor-5 alpha-androstane compounds in preparation of malignant tumor resistant medicaments
  • Applicationof A-nor-5 alpha-androstane compounds in preparation of malignant tumor resistant medicaments
  • Applicationof A-nor-5 alpha-androstane compounds in preparation of malignant tumor resistant medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 Preparation of 2α, 17α-bisethynyl-A-abortion-5α-androstane-2β, 17β-dihydroxy compound (Ia)

[0044] Suspend 30g of KOH powder in 60ml of THF, cool to below 5°C and pass through acetylene until no absorption, then dissolve 10g of A-anorsandrostane-2,17-dione in 100ml of THF, add dropwise to the flask, pass through acetylene until thin The raw material disappeared in layer chromatography, slowly added 18ml of water dropwise under stirring, stirred for 30 minutes, separated the lower aqueous layer, concentrated the organic layer to dryness under reduced pressure, added 100mL of ethyl acetate to dissolve, washed with water until the pH was 7, and 5g of activated carbon Decolorize, filter, and concentrate the filtrate to dryness under reduced pressure. The viscous solid obtained is refluxed and dissolved in 150 mL of n-hexane-benzene mixed solvent with a volume ratio of 1:1. After cooling, crystals are precipitated, filtered, and the filter cake is dried to obtain 2...

Embodiment 2

[0045] Example 2 Preparation of 2α, 17α-bisethynyl-A-abortion-5α-androstane-2β, 17β-dihydroxydiacetate (Ib)

[0046] Dissolve 2g of Ia in 20mL of pyridine, add 20mL of acetic anhydride and 0.1g of sodium acetate, reflux for 10 hours, cool to 20°C after the reaction is complete, slowly add 30mL of methanol dropwise, add 20mL of saturated saline, and use ethyl acetate (15mL*3 ), combined organic layers, washed with water until the pH was 7, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure, and the obtained solid was dissolved in 20 mL of methanol at 65 ° C, cooled to 20 ° C and left for 24 hours, and the solid was precipitated. Filter and dry the filter cake to obtain 1.3g of 2α, 17α-diethynyl-A-carbocarb-5α-androstane-2β, 17β-bishydroxydiacetate (Ib), mp190-191°C, [α ] D 25 -39° (C=1, CHCl 3 ).

Embodiment 3

[0047] Example 3 Preparation of 2α, 17α-bisethynyl-A-abort-5α-androstane-2β, 17β-dihydroxydipropionate (Ic)

[0048] Dissolve 2g of Ia in 20mL of pyridine, add 20mL of propionic anhydride and 0.1g of sodium acetate, reflux for 10 hours, cool to 20°C after the reaction is complete, slowly add 30mL of methanol dropwise, add 20mL of saturated saline, and use ethyl acetate (15mL*3 ), combined the organic layers, washed with water until the pH was 7, dried over anhydrous sodium sulfate, filtered, and concentrated the filtrate to dryness under reduced pressure. Crystals were filtered and the filter cake was dried to obtain 2α, 17α-bisethynyl-A-aborb-5α-androstane-2β, 17β-dihydroxydipropionate (Ic) 2g, mp152-153°C, [ α] D 25 -32° (C=1, CHCl 3 ).

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Abstract

The invention discloses application of A-nor-5 alpha-androstane compounds in preparation of malignant tumor resistant medicaments. The compounds have the following general formula I, and comprise Ia, Ib, Ic, Id, Ie and If. The growth inhibition rate of the A-nor-5 alpha-androstane compounds for in-vitro human liver cancer cell Hep 3B, human breast cancer MDA-MB-231, human lung adenocarcinoma A549and mouse melanoma B16 is higher than 85% on average, and even up to 99.98% to the maximum. The in-vivo test proves that the inhibition rate of the A-nor-5 alpha-androstane compounds for mouse tumors, such as intestinal cancer C26, liver cancer H22, Lewis lung cancer, breast cancer, B16 melanoma and the like, is higher than 50% on average, and even up to 63.19% to the maximum. The result proves that the compounds disclosed by the invention have an obvious malignant tumor resistant action. The A-nor-5 alpha-androstane compounds disclosed by the invention have an obvious and broad-spectrum action on inhibiting growth of malignant tumor cells, and are novel targeted malignant tumor resistant medicaments with low drug toxicity and favorable treatment effect; and the A-nor-5 alpha-androstane compounds just specifically act on tumor cells, but not influence normal cells, thereby having a high clinical application value.

Description

technical field [0001] The invention relates to medicinal chemistry, in particular to the application of A-carbo-5α-androstane compound in the preparation of anti-malignant tumor drugs. Background technique [0002] Malignant tumors have gradually replaced cardiovascular and cerebrovascular diseases as the world's number one killer. The 2010 Cancer Report issued by the Fifth Asia-Pacific Organization for Cancer Prevention Congress warned that the number of cancer patients in the world will rise rapidly in the next 20 years. From 2008 to 2030, the number of new cancer patients worldwide will increase from 12.4 million per year to 26.4 million, of which patients in the Asia-Pacific region account for 60% of the total number of cancer patients in the world. [0003] In 2007, 7.6 million people died of malignant tumors worldwide. In developed countries, cancer mortality accounts for 21.6% of the total deaths. In China, the incidence of malignant tumors has risen significantly...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/569A61P35/00C07J61/00
CPCA61K31/568A61P35/00
Inventor 李瑞麟曹振全谌志华陈雅君
Owner SHANGHAI AO QI MEDICAL TECH
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