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Tetra hydro iso quinoline compounds possessing anti breed and anti fungus activity and its salt

A tetrahydroisoquinoline, anti-fertility technology, applied in the field of medicine, can solve the problems of affecting clinical treatment, high toxicity of drugs, limiting clinical application and the like

Inactive Publication Date: 2006-06-14
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, azole antifungal drugs are highly toxic and prone to drug resistance, which seriously affects clinical treatment.
[0003] Oral contraceptives currently clinically used are mainly steroid hormones, which have side effects of hormones; external contraceptives are mainly nonionic surfactants, such as nonoxynol, which are irritating to the mucous membranes. Side effects such as injury also limit its clinical application

Method used

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  • Tetra hydro iso quinoline compounds possessing anti breed and anti fungus activity and its salt
  • Tetra hydro iso quinoline compounds possessing anti breed and anti fungus activity and its salt
  • Tetra hydro iso quinoline compounds possessing anti breed and anti fungus activity and its salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation of embodiment 1,2-dodecyl-6,7-dihydroxyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (compound 1 in table 1)

[0037] Add 20ml of 3,4-dimethoxy-phenylethylamine and 3.60g of paraformaldehyde to absolute ethanol, stir and react at room temperature until the paraformaldehyde is completely reacted, adjust the pH of the solution to 2 with dilute hydrochloric acid, and heat to reflux for 4 hours , cooled, precipitated solid, filtered, added the resulting solid to 10% NaOH solution, and then added CH 2 Cl 2 100ml, shake, separate CH 2 Cl 2 layer, anhydrous K 2 CO 3 Dry, filter, and remove the solvent under reduced pressure to obtain 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline as a pale yellow solid.

[0038] Take the compound 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 1g and 0.6g dodecane bromide obtained above, K 2 CO 3 1g was dissolved in 30ml of absolute ethanol, stirred and refluxed for 8h, allowed to cool, filtered, and the solvent was evaporat...

Embodiment 2

[0056] The preparation of embodiment 2,2-dodecyl-6,7-diacetoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (compound 4 in table 1)

[0057] Get 3.5g 6,7-dihydroxyl-2-dodecyl-1,2,3,4-tetrahydroisoquinoline hydrobromide and join in 5ml pyridine and 30ml dichloromethane solution, ice bath cooling, Slowly add 8ml of acetic anhydride dropwise under stirring, after the addition is complete, stir at room temperature for 4h, then heat to reflux for 3h. Let it cool, and the reaction solution was washed with NaHCO 3 Aqueous solution and water wash. Na for reaction solution 2 CO 3 After drying, the solvent was evaporated to obtain a yellow solid. The solid was dissolved in 30ml of absolute ethanol, and HCl gas was introduced to saturation under an ice bath, and the solid was precipitated after standing, filtered, and dried to obtain 6,7-diacetoxy-2-dodecyl-1,2, 3,4-tetrahydroisoquinoline hydrochloride.

[0058] The following compounds are prepared by the method of Example 2:

[0...

Embodiment 3

[0060] Embodiment 3, the preparation of 2-decyl-6,8-dihydroxyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (compound 22 in table 1)

[0061] 18 g of 3,5-dihydroxyphenethylamine was reacted with 3.6 g of paraformaldehyde, and the method was the same as in Example 1 to obtain 6,8-dihydroxy-1,2,3,4-tetrahydroisoquinoline.

[0062] The intermediate 6.1g prepared above, bromodecane 6.2g, anhydrous K 2 CO 3 5.6 g and 150 ml of acetonitrile, stirred at room temperature for 16 hours, removed the solvent under reduced pressure, dissolved in ethyl acetate, washed with water, dried, and passed through HCl gas to obtain 2-decyl-6,8-dihydroxy-1,2,3 , 4-tetrahydroisoquinoline hydrochloride.

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Abstract

The present invention relates to a kind of new-type tetrahydroisoquinoline compound with antifertility activity and antifungal activity and its pharmaceutically-acceptable salt. Said compound can be used for preparing antifertility medicine and antifungal medicine. Said invention also provides the structure general formula of said compound.

Description

technical field [0001] The invention relates to the technical field of medicine, and relates to a class of novel tetrahydroisoquinoline compounds and their addition salts with antifertility and antifungal activities. Background technique [0002] Fungal diseases are common and frequently-occurring diseases. In recent years, the incidence of deep fungal infection has increased significantly. The antifungal drugs currently used clinically are mainly nitrogen azoles such as fluconazole and ketoconazole. The antifungal mechanism of this class of drugs is as follows: nitrogen azoles pass through the N in their structure 3 or N 4 Unused electron pairs on atoms and fungal C 14α The heme prosthetic group Fe atom of the demethylase binds to inhibit the enzyme activity, thereby exerting antifungal effect. But because this enzyme belongs to the member of cytochrome P450 superfamily protein, cytochrome P450 enzyme system is common in human body, and azol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/04A61K31/472A61P15/18A61P31/10
Inventor 周有骏吕加国朱驹周晓天
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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