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Fluoroquinolone-methyl thiazolyl tetrazolium heterozygous derivative, preparation method and application thereof

A compound, nitrogen oxide technology, applied in the direction of pharmaceutical formulations, medical preparations containing active ingredients, organic active ingredients, etc.

Active Publication Date: 2018-12-28
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, a lot of practice has shown that although the backbone integration method is theoretically feasible, it is unpredictable whether the affinity for the original target can still be retained because the structure and physical and chemical properties of the integrated compound may be very different from those before the integration.

Method used

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  • Fluoroquinolone-methyl thiazolyl tetrazolium heterozygous derivative, preparation method and application thereof
  • Fluoroquinolone-methyl thiazolyl tetrazolium heterozygous derivative, preparation method and application thereof
  • Fluoroquinolone-methyl thiazolyl tetrazolium heterozygous derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1, the synthesis of TM1 series compounds

[0041] The general route is as follows:

[0042]

[0043] Add 2',4'-difluoro-2-[1-(1H-1,2,4-triazolyl)]acetophenone (1.115g, 5mmol) and 10mL methanol into a 250mL round bottom flask, stir at room temperature , add KBH in batches under ice bath condition 4 (0.405g, 7.5mmol), the addition was completed, the ice bath was removed, stirred at 20-40°C, and the reaction progress was detected by TLC. After the reaction is complete, remove the solvent by rotary evaporation, add 15 mL of water, adjust the pH to 1-3 with concentrated hydrochloric acid, stir at room temperature for 1 h, and add 10% K 2 CO 3 Adjust the pH to 8-9, let stand, filter with suction, and wash with water (10 mL×3) to obtain IM1 as a white solid.

[0044] In a 100mL round bottom flask, add IM1 (0.672g, 3mmol), succinic anhydride (0.603g, 6mmol), acetone 6mL, Et 3 N 0.15mL, heated to reflux with stirring, and monitored the reaction progress by TLC. ...

Embodiment 2

[0050] Embodiment two, the synthesis of TM2 series compounds

[0051] The general route is as follows:

[0052]

[0053] Add NaH (0.813g, 20mmol) and THF 15mL to a 250mL three-necked flask, stir at room temperature; slowly add dropwise a solution of IM1 (2.245g, 10mmol) dissolved in THF 10mL with a constant pressure dropping funnel, and transfer to an 80°C oil bath for reaction 30 min; a solution of methyl 2-bromoacetate (1.735 g, 15 mmol) dissolved in THF 10 mL was slowly added dropwise. The progress of the reaction was monitored by TLC. Stirring was stopped, and the reaction mixture was concentrated under reduced pressure, poured into cold water (30 mL), and extracted with dichloromethane (2×20 mL). The organic extracts were combined, washed with saturated brine (2×20 mL), dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, purified by column chromatography (PE / EA=1 / 2), collected the eluent, evaporated to dryness under reduced pressure, V...

Embodiment 3

[0059] Embodiment three, the synthesis of TM3 series compound

[0060] The general route is as follows:

[0061]

[0062] In a 100mL round bottom flask, add Floxacin (2mmol), DCM 5mL and alkali (NaHCO 3 or Et 3 N, 3 mmol), stirred in an ice bath, 5 mL of a DCM solution of 1 mmol of solid phosgene (BTC) was added dropwise, stirred at room temperature, and the reaction progress was monitored by TLC. After the reaction, add 15 mL of saturated saline to adjust the pH to 4-5, separate the liquids, and wash with saturated saline (10 mL×3). The liquid was separated, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain intermediates IM3-1-IM3-8.

[0063] In a 100mL round bottom flask, add IM1 (1.2mmol), DCM 10mL, Et 3 N (1.5mmol) and DMAP (0.05mmol), stirred in an ice bath, added IM3-X (X = 1 ~ 8) (1mmol), warmed up to room temperature, continued to stir, TLC to monitor the reaction progress. After the reaction, add 15mL DCM, and was...

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Abstract

The invention discloses a fluoroquinolone-methyl thiazolyl tetrazolium heterozygous derivative as shown in formula I. The derivate is characterized in that pharmacophores of fluoroquinolone and methylthiazolyl tetrazolium type medicines are interconnected through proper connection structures; the bioactivity experiment verifies that the compound has bacteria and fungus inhibiting activity and hasgood application prospect.

Description

technical field [0001] The present invention relates to a class of compounds used for treating bacterial and / or fungal infections, especially to ten series of fluoroquinolone-oxazole hybrid derivatives. Background technique [0002] With the wide application of broad-spectrum antibiotics, hormones, and immunosuppressants, the spread of AIDS, the popularization and application of organ transplantation and interventional techniques, the incidence of microbial infections such as fungi and bacteria is on the rise, and reports on drug-resistant strains are gradually increasing. , the treatment of fungal and bacterial infections is facing severe challenges. [0003] Azole antifungal drugs are currently the main drugs for the treatment of fungal infections in clinical practice. These drugs have stable metabolism, can be taken orally or injected, and have the advantages of being effective for both superficial fungi and deep fungi. Among them, arylethyl cyclic ketal compounds such a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D401/14C07D401/12A61P31/04A61P31/10A61K31/4709A61K31/496A61K31/506
CPCA61P31/04A61P31/10C07D401/12C07D401/14C07D471/04Y02A50/30
Inventor 杨大成陈菲菲范莉罗鹏张书虹潘建芳徐兴然聂福平陈冉樾张园张泽朝胡军华王帆周成合刘耀
Owner SOUTHWEST UNIVERSITY
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