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Chiral azodipyrrole and application thereof to preparation of drug for inhibiting pathogenic bacteria infection

A technology of heterodipyrrole and pathogenic bacteria, applied in the field of chiral azadipyrrole antibacterial drugs and its application, can solve problems such as bacterial infection, life-threatening of patients, sepsis, etc.

Active Publication Date: 2018-06-08
INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Bacterial infectious disease is a common clinical disease. If it is not treated in time, it may cause severe bacterial infection, sepsis, and endanger the life of the patient, with a high mortality rate

Method used

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  • Chiral azodipyrrole and application thereof to preparation of drug for inhibiting pathogenic bacteria infection
  • Chiral azodipyrrole and application thereof to preparation of drug for inhibiting pathogenic bacteria infection
  • Chiral azodipyrrole and application thereof to preparation of drug for inhibiting pathogenic bacteria infection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A kind of chiral azadipyrrole is prepared by the following method:

[0030] 1) Compound 2 (10mmol, 3.4g) was dissolved in CH 2 Cl 2 (50mL), add CH 3 OCH 2 Cl (12mmol, 0.8g), i- PR 2 NEt (catalyst), at 25°C, reacted for 1 h, monitored by TLC, separated by extraction and separated by column chromatography to obtain compound 3a (3.64 g, yield 95%).

[0031] 2) Will 10mmol, 2.83g) was dissolved in THF (50mL), adding compound 3a (0.8mmol, 3.07g), NaHCO 3 (10mmol, 0.84g), stirred at room temperature for 1h, monitored by TLC, extracted and separated, separated by column chromatography, concentrated for later use;

[0032] 3) Dissolve the concentrate obtained in step (2) in methanol (50mL), add a catalytic amount of HCl dropwise, 50°C, 10min, extract and separate, and separate by column chromatography to obtain compound I-5 (4.71g, 96% ). 1H NMR (300MHz, CDCl3)δ

[0033] 7.16-7.26(m, 2H), 7.11(d, J=8.7Hz, 1H), 6.78-6.86(m, 2H), 6.98(dd, J=8.7, 6.2Hz, 1H), 6.23(dd, J=...

Embodiment 2

[0035] A kind of chiral azadipyrrole is prepared by the following method:

[0036] 1) with Alternative to Example 1 Other is with embodiment 1, obtains compound I-6

[0037] (4.71 g, 96%).

Embodiment 3

[0039] A kind of chiral azadipyrrole is prepared by the following method:

[0040] 1) Compound 2 (10mmol, 3.4g) was dissolved in CH 2 Cl 2 (50mL), add CH 3 OCH 2 Cl (12mmol, 0.8g), i- PR 2 NEt (catalyst), at 25°C, reacted for 1 h, monitored by TLC, separated by extraction and separated by column chromatography to obtain compound 3a (3.64 g, yield 95%). ;

[0041] 2) Will ( 10mmol, 2.83g) was dissolved in THF (50mL), adding compound 3a (0.8mmol, 3.07g), NaHCO 3 (10mmol, 0.84g), stirred at room temperature for 1h, monitored by TLC, separated by extraction, concentrated by drying, and separated by column chromatography to obtain compound I-8 (4.57g, 80%).

[0042] 3) Dissolve the concentrate obtained in step (2) in methanol (50mL), add a catalytic amount of HCl dropwise, 50°C, 10min, extract and separate, and separate by column chromatography to obtain compound I-7 (4.85g, 98% ).

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Abstract

The invention discloses chiral azodipyrrole and application thereof to preparation of a drug for inhibiting pathogenic bacteria infection. The chiral azodipyrrole is characterized by being shown as aformula (I) or (II). An experiment proves that the chiral azodipyrrole disclosed by the invention shows the activity for staphylococcus aureus, methicillin-resistant staphylococcus aureus, escherichiacoli, candida albicans, tramycin, cryptococcus neoformans and dermatophytes.

Description

technical field [0001] The invention belongs to the field of organic synthesis and medicine, and in particular relates to a chiral azadipyrrole antibacterial drug for treating bacterial and fungal infections and its application. Background technique [0002] Bacterial infectious disease is a common clinical disease. If it is not treated in time, it may cause severe bacterial infection, sepsis, and endanger the life of the patient, with a high mortality rate. Especially in recent years, the abuse of antibiotics has led to the emergence of various antibiotic-resistant bacteria and superbugs, and the threats we face are becoming increasingly serious. Some developed countries spend huge sums of money on health care in order to prevent infectious diseases. The annual loss due to hospital-acquired infection is about hundreds of millions of yuan, and the average annual death rate of about 5,000 people is due to infection. In such an increasingly severe situation, there is an urgen...

Claims

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Application Information

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IPC IPC(8): C07F5/02A61P31/04A61P31/10
CPCC07B2200/07C07F5/02Y02A50/30
Inventor 陆丽张宇
Owner INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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