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B-norcholestane benzimidazole compound as well as preparation method and application thereof

A benzimidazole and compound technology, applied in the field of compound preparation, can solve the problems of high toxicity and limited use range, and achieve the effects of low damage, simple preparation method, and increased inhibition rate

Inactive Publication Date: 2015-03-25
NANJING GREEPHARMA INC LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, various types of anti-tumor drugs continue to emerge and have been applied clinically, but the clinically used anti-tumor drugs have greatly limited their scope of use due to their high toxicity to human tissues

Method used

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  • B-norcholestane benzimidazole compound as well as preparation method and application thereof
  • B-norcholestane benzimidazole compound as well as preparation method and application thereof
  • B-norcholestane benzimidazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Preparation of 2-(B-nor-3',5'-dihydroxy-6'-cholestanyl)-5-fluorobenzimidazole.

[0055] Step 1. Put 400mg of cholesterol in a large test tube, add 20mL of dichloromethane and 5mL of methanol, mix, place in a liquid nitrogen-cooled Dewar flask, cool to -60°C, and pass through an ozone-rich Oxygen flowed until the reaction was completed, and ozone was stopped after 20 minutes. At this time, the solution turned light blue, and then 1 mL of dimethyl sulfide was added, and the temperature was raised to 20 ° C. Stirring, the solvent was removed from the stirred substance to obtain a colorless The oily substance is the first compound;

[0056] Step 2. Put 400mg of the first compound in a 100mL round bottom flask, add 20mL of benzene and 2g of neutral alumina, mix and stir at 25°C, and separate the reacted material on a silica gel column. The substance after removing the solvent is purified to obtain the second compound;

[0057] Step 3. Put 350mg of the second compound in a ...

Embodiment 2

[0064] Preparation of 2-(B-nor-3',5'-dihydroxy-6'-cholestanyl)-5-nitrobenzimidazole.

[0065] Step 1. Put 600mg of cholesterol in a large test tube, add 60mL of dichloromethane and 15mL of methanol, mix, place in a liquid nitrogen-cooled Dewar flask, cool to -90°C, and pass through an ozone-rich Oxygen flowed until the reaction was completed, and ozone was stopped after 40 minutes. At this time, the solution turned light blue, and then 8 mL of dimethyl sulfide was added, heated to 35 ° C, stirred, and the solvent was removed from the stirred substance to obtain a colorless The oily substance is the first compound.

[0066] Step 2. Put 600mg of the first compound in a 100mL round bottom flask, add 40mL of benzene and 7g of neutral alumina, mix and stir at 25°C, and separate the reacted material on a silica gel column. The resulting substance was removed from the solvent and purified to obtain the second compound.

[0067] Step 3. Put 500mg of the second compound in a 100mL ro...

Embodiment 3

[0074] Preparation of 2-(B-nor-3',5'-dihydroxy-6'-cholestanyl)-5-trifluoromethylbenzimidazole.

[0075] Step 1. Put 500mg of cholesterol in a large test tube, add 40mL of dichloromethane and 10mL of methanol, mix, place in a liquid nitrogen-cooled Dewar flask, cool to -78°C, and pass through an ozone-rich Oxygen flowed until the reaction was completed, and ozone was stopped after 30 minutes. At this time, the solution turned light blue, and then 4 mL of dimethyl sulfide was added, heated to 25 ° C, stirred, and the solvent was removed from the stirred substance to obtain a colorless The oily substance is the first compound.

[0076] Step 2. Put 566mg of the first compound in a 100mL round bottom flask, add 30mL of benzene and 5g of neutral alumina, mix and stir at 25°C, and separate the reacted material on a silica gel column. The resulting substance was removed from the solvent and purified to obtain the second compound.

[0077] Step 3: Put 327mg of the second compound in ...

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Abstract

The invention provides a B-norcholestane benzimidazole compound as well as a preparation method and application thereof. The general structural formula of the compound is as shown in the specification, wherein R refers to any one of H or COCH3; R1 refers to F, NO2, CF3, H, CH3 or OCH3; and R2 refers to H or CH3. The B-norcholestane benzimidazole compound disclosed by the invention has high inhibitory activity on human cervical carcinoma cell lines, human lung carcinoma cell lines and human liver cancer cells. The B-norcholestane benzimidazole compound disclosed by the invention is low in toxicity and low in injury of normal cells, has an effective effect of inhibiting the cancer cells during low concentration, basically does not cause drug injury to normal cells and can be applied to preparing medicines for treating the cancers.

Description

technical field [0001] The invention relates to the field of compound preparation, more specifically, the invention relates to a B-norcholestane benzimidazole compound and its preparation method and application. Background technique [0002] Cancer is a major disease that endangers human health. Overcoming malignant tumors is a difficult problem in modern medicine, and it is also the biggest challenge for the pharmaceutical industry today. At present, various types of anti-tumor drugs are continuously emerging and used clinically, but the anti-tumor drugs used in clinical practice are highly toxic to human tissues, which greatly limits their scope of use. Therefore, finding anticancer drugs with high efficiency, high selectivity and small side effects is the main direction of anticancer drug development. [0003] Among the antineoplastic drugs, finasteride (Finasteride), which is currently clinically used to treat benign prostatic hyperplasia, and estramustine phosphate sod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J61/00A61P35/00
CPCC07J61/00
Inventor 崔建国戚斌斌黄燕敏甘春芳刘志平
Owner NANJING GREEPHARMA INC LTD
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