Propylene tethered ciprofloxacin-isatin hybrids as well as synthetic method and application thereof

A technology of indolindione and ciprofloxacin, which is applied in the field of medicinal chemistry and can solve the problems of poor therapeutic effect on bacterial infections

Inactive Publication Date: 2018-11-02
王若
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, like other types of antimicrobials, bacterial pathogens develop resistance to fluoroquinolones rapidly, and the main reason for this serious situation

Method used

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  • Propylene tethered ciprofloxacin-isatin hybrids as well as synthetic method and application thereof
  • Propylene tethered ciprofloxacin-isatin hybrids as well as synthetic method and application thereof
  • Propylene tethered ciprofloxacin-isatin hybrids as well as synthetic method and application thereof

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Embodiment 1

[0029] figure 1 The synthesis routes of propylene-tethered indolindione-ciprofloxacin hybrids 3a-f and 4a-f are given. Alkylation of C-5-substituted indolindione 1a,b with 1,3-dibromopropane in the presence of potassium carbonate to generate N-(3-bromopropyl)indolindione 2a ,b, and then these intermediate products are incorporated into the CPFX core, and then the expected target products 3a,b and bis-indolindione-ciprofloxacin hybrids 4a,b can be obtained. Subsequently, the hybrids 3a,b or 4a,b were condensed with methylhydroxylamine or ethylhydroxylamine hydrochloride in the presence of sodium bicarbonate to generate other conjugates 3c-f and 4c-f.

[0030] In this study, all propylene-tethered indolindione-ciprofloxacin hybrids 3a-f and 4a-f were tested for their in vitro antibacterial activity against clinically typical Gram-positive and Gram-negative bacteria. evaluation, and also on the MTB H 37 The antimycobacterial activity of Rv and MDR-TB strains was evaluated. Am...

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Abstract

The invention discloses propylene tethered ciprofloxacin-isatin hybrids as well as a synthetic method and an application thereof. The prepared ciprofloxacin-isatin hybrid 3d have strong resistance toall tested Gram-positive bacteria and Gram-negative bacteria (including pathogens showing strong drug resistance clinically), and efficacy of 3d is equivalent to or even better than the parent ciprofloxacin or levofloxacin; antibacterial activity of hybrid 3b (MIC: 0.10 and 0.5 mu g/mL) for an mycobacterium tuberculosis H37Rv strain is 4 times and 8 times that of ciprofloxacin (MIC: 0.78 mu g/mL)and rifampicin (MIC: 0.39 mu g/mL), and antibacterial activity of the hybrid 3b for multi-drug resistant tuberculosis is 4->256 times that of three reference drugs including ciprofloxacin (MIC: 2.0 mug/mL), rifampicin (MIC: 32 mu g/mL) and isoniazid (>128 mu g/mL). The hybrids 3b and 3d with lower cytotoxicity (CC50: 64 and 256 mu g/mL) show acceptable metabolic stability and in-vivo PK (pharmacokinetics) characteristics.

Description

technical field [0001] The patent belongs to the field of medicinal chemistry, and in particular relates to a propylene tethered ciprofloxacin-indolindione hybrid compound and its synthesis method and application. Background technique [0002] Bacterial infections caused by gram-positive and gram-negative bacteria, as well as mycobacterial pathogens, are the leading cause of hospital-acquired infections, resulting in a large number of deaths and imposing an enormous burden on healthcare systems worldwide. The latest report from the World Health Organization (WHO) estimates that approximately 10 million people die from infectious diseases each year (accounting for more than 15% of all deaths), and that tuberculosis (TB) is the ninth leading cause of death globally and is also the result of a single infection. source of the main reason. In recent years, such as methicillin-resistant Staphylococcus aureus (MRSA), methicillin-resistant Staphylococcus epidermidis (MRSE), vancomy...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D401/14A61P31/04A61P31/06A61K31/496
CPCC07D401/12A61P31/04A61P31/06C07D401/14
Inventor 王若殷雪旸张姚欢闫玮涛
Owner 王若
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