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Chiral azadipyrrole and its application in the preparation of drugs 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 the problems of life-threatening, high mortality and bacterial infection of patients

Active Publication Date: 2019-12-27
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 azadipyrrole and its application in the preparation of drugs for inhibiting pathogenic bacteria infection
  • Chiral azadipyrrole and its application in the preparation of drugs for inhibiting pathogenic bacteria infection
  • Chiral azadipyrrole and its application in the preparation of drugs for inhibiting pathogenic bacteria infection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0030] 1) Compound 2 (10 mmol, 3.4 g) 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, extracted and separated, 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), compound 3a (0.8mmol, 3.07g) was added, NaHCO 3 (10mmol, 0.84g), stirred at room temperature for 1h, monitored by TLC, extracted and separated, separated by column chromatography, and concentrated for later use;

[0032] 3) The concentrate of (2) obtained in the step was dissolved in methanol (50 mL), and a catalytic amount of HCl was added dropwise at 50° C. for 10 min, followed by extraction and separation, and column chromatography to obtain compound I-5 (4.71 g, 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,...

Embodiment 2

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

[0036] 1) with Alternative to Example 1 Others are the same as in Example 1 to obtain compound I-6

[0037] (4.71 g, 96%).

Embodiment 3

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

[0040] 1) Compound 2 (10 mmol, 3.4 g) 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, extracted and separated, 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), compound 3a (0.8mmol, 3.07g) was added, NaHCO 3 (10 mmol, 0.84 g), stirred at room temperature for 1 h, monitored by TLC, extracted and separated, dried and concentrated, and separated by column chromatography to obtain compound I-8 (4.57 g, 80%).

[0042] 3) Dissolve the concentrate of (2) obtained in the step in methanol (50 mL), add dropwise a catalytic amount of HCl, 50° C., 10 min, extract and separate, and separate by column chromatography to obtain compound I-7 (4.85 g, 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 azabipyrrole antibacterial drug for treating bacterial and fungal infections and its application. Background technique [0002] Bacterial infectious disease is a common clinical disease. If not treated in time, it may cause severe bacterial infection and sepsis, endanger the life of patients, and have 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 we are facing an increasingly serious threat. Some developed countries spend huge sums of money on health care for the prevention of infectious diseases. The annual loss of hospital-acquired infections is about 100 million yuan, and about 5,000 people die each year due to infections. Under such increasingly severe circumstances, a new therapeutic drug against pathogenic bacteria is urgently...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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