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Isorcryptolepine analogue prepared by taking pefloxacin as raw material as well as preparation method and application thereof

A technology of isoberaline and pefloxacin, applied in organic chemistry, antibacterial drugs, etc., can solve the problems of difficult sources of albino alkaloids, poor water solubility, and low bioavailability, and achieve excellent in vitro Inhibit the growth activity of Mycobacterium tuberculosis, increase osmosis, improve the effect of water solubility

Inactive Publication Date: 2021-12-21
ZHENGZHOU UNIV OF IND TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, due to the difficulty in the source of vine alkaloids, coupled with poor water solubility, resulting in low bioavailability and other defects, the clinical application is limited.

Method used

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  • Isorcryptolepine analogue prepared by taking pefloxacin as raw material as well as preparation method and application thereof
  • Isorcryptolepine analogue prepared by taking pefloxacin as raw material as well as preparation method and application thereof
  • Isorcryptolepine analogue prepared by taking pefloxacin as raw material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 2-fluoro-3- (4-methyl-piperazin-1-yl) -5-ethyl -5H- indolo [3,2-c] quinoline (I-1), the chemical structural formula:

[0037]

[0038] I.e. Ⅰ formula wherein R is a H atom.

[0039] The method for preparing the compound (I-1) are: 1-ethyl-6-fluoro-take-7- (4-methylpiperazin-1-yl) -2,3-dihydro - quinoline -4 (1H ) - -one 1.0g (3.4mmol) was dissolved in 15mL anhydrous ethanol was added phenylhydrazine 0.50g (4.6mmol), the reaction was stirred for 20h at room temperature (TLC ⅲ observe the disappearance of starting material), a large amount of precipitate formed. Concentrated hydrochloric acid (0.50 mL) as the cyclization catalyst, the reaction mixture was refluxed for 12h, allowed to stand overnight (12h, the same below). The resulting solid was filtered, and the solid body was dissolved with 50 ml of deionized water, and the appropriate amount of activated carbon was added, and the reflux was dissolved for 1 h. Hot filtration, the filtrate was adjusted with aqueous ammonia...

Embodiment 2

[0041] Ethyl-8-fluoro-5-methoxy-3- (4-methyl-piperazin-1-yl) -5H- indolo [3,2-c] quinoline (I-2), The chemical structure of the formula:

[0042]

[0043] I.e. Ⅰ formula wherein R is methoxy.

[0044] The method for preparing the compound (I-2) are: The 1-ethyl-6-fluoro-7- (4-methylpiperazin-1-yl) -2,3-dihydro - quinoline -4 (1H ) - -one 1.0g (3.4mmol) was dissolved in 15mL anhydrous ethanol was added p-methoxybenzyl hydrazine 0.62g (4.5mmol), stirred at room temperature overnight (TLC ⅲ observe the disappearance of starting material), a clear precipitate formed. Concentrated hydrochloric acid (0.50mL), the reaction mixture was refluxed for 16h, allowed to stand overnight. The resulting solid was filtered, and the solid body was dissolved with 50 ml of deionized water, and the appropriate amount of activated carbon was added, and the reflux was dissolved for 1 h. Hot filtration, the filtrate was adjusted with aqueous ammonia pH≈10.0. The solid was collected by filtration, dried ...

Embodiment 3

[0046] 2-fluoro-5-ethyl-3- (4-methyl-piperazin-1-yl) -9-methoxy--5H- indolo [3,2-c] quinoline (I-3), The chemical structure of the formula:

[0047]

[0048] I.e. Ⅰ formula wherein R is methoxy.

[0049] The method for preparing the compound (I-3) are: taking ethyl-6-fluoro-7- (4-methylpiperazin-1-yl) -2,3-dihydro - quinoline -4 (1H ) - -one 1.0g (3.4mmol) was dissolved in 15mL absolute ethanol was added between methoxyphenylhydrazine 0.83g (6.0mmol), the reaction 24h (TLC the disappearance of starting material was observed ⅲ) was stirred at room temperature, the precipitate formed appears obvious. Concentrated hydrochloric acid (0.50mL), the reaction mixture was refluxed for 12h, allowed to stand overnight. The resulting solid was filtered, and the solid body was dissolved with 50 ml of deionized water, and the appropriate amount of activated carbon was added, and the reflux was dissolved for 1 h. Hot filtration, the filtrate was adjusted with aqueous ammonia pH≈10.0. The solid...

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PUM

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Abstract

The invention discloses an analogue from pefloxacin to isocryptolepine as well as a preparation method and application thereof. The analogue is characterized in that a chemical structure is shown as a formula I, wherein a substituent group R in the formula I can be independently -H, -OCH3, -F, -Cl or -SO2NH2. According to the isocryptolepine analogue disclosed by the invention, pefloxacin is taken as a raw material, so that effective chemical construction from a fluoroquinolone structure to an indoloquinoline skeleton is realized, a new way for structural modification of isocryptolepine is expanded, complementary advantage structures of fluoroquinolone medicines and natural indoloquinoline alkaloids are achieved, further, the anti-tubercle bacillus activity and the anti-drug resistance of the compound are improved, the toxicity to normal cells is reduced, and the compound can be further developed as an anti-tubercle medicine with a brand new structure.

Description

Technical field [0001] In the field of pharmaceutical chemical technology related to organic synthesis and new drug development, the present invention relates to a method of preparing alkaline analogues for the preparation of ablated coil alkali analogs in the preparation of a white-prolinal alkali analog. Application in anti - tuberculosis drugs. Background technique [0002] Tuberculosis is a chronic infectious disease caused by tuberculosis. Due to lack of effective treatment, it has become an urgent public health and social issue facing the world. At the same time, in addition to the production of drug resistance, especially multidrug drug resistance, in particular the production of multidrug drug resistance, in particular for the development of anti-tuberculosis drugs There is no new compound for tuberculosis treatment. Therefore, the research and development of anti-tuberculosis drugs is a high-time, high-input complex intellectual innovation project being concerned. Among ...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61P31/06
CPCC07D471/04A61P31/06
Inventor 邵香敏周敬张素红师璟王春燕
Owner ZHENGZHOU UNIV OF IND TECH
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