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Method for synthesizing albomycin delta 1, albomycin delta 2 and albomycin epsilon, and application of albomycin delta 1, albomycin delta 2 and albomycin epsilon as antibacterial drugs

A synthetic method and antibacterial drug technology, applied in the synthesis of δ2 and ε, the application of antibacterial drugs, and the natural product albomycin δ1, which can solve the problems of limited sources and difficulty in obtaining sufficient quantities of compounds, etc.

Inactive Publication Date: 2019-12-03
CHONGQING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the limited sources of such natural products, it is difficult to obtain a sufficient amount of compounds through separation and extraction for subsequent pharmacological and toxicological studies

Method used

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  • Method for synthesizing albomycin delta 1, albomycin delta 2 and albomycin epsilon, and application of albomycin delta 1, albomycin delta 2 and albomycin epsilon as antibacterial drugs
  • Method for synthesizing albomycin delta 1, albomycin delta 2 and albomycin epsilon, and application of albomycin delta 1, albomycin delta 2 and albomycin epsilon as antibacterial drugs
  • Method for synthesizing albomycin delta 1, albomycin delta 2 and albomycin epsilon, and application of albomycin delta 1, albomycin delta 2 and albomycin epsilon as antibacterial drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015]

[0016] Synthesis of compound i-2

[0017] At room temperature, a dichloromethane solution (100 mL) of benzoyl peroxide (2.90 g, 12.0 mmol, 1.2 equiv) was rapidly added to pH=10.5 of i-1 (2.88 g, 10.0 mmol, 1.0 equiv). in the buffer solution. After reacting at room temperature for 3 hours, a dichloromethane solution (12 mL) of acetyl chloride (0.72 mL, 10.0 mmol, 1.0 equiv) was added to the reaction solution, and stirred until the reaction was completed. Extraction, spin-drying, and silica gel column chromatography gave compound i-2 (3.6 g, 80%). 1 H NMR (400MHz, CDCl 3 )δ8.11–8.06(m,2H),7.67(t,J=7.4,1H),7.51(t,J=7.7,2H),5.20–4.65(m,1H),4.22–3.96(m,1H ), 3.83(t,J=6.3,2H), 2.06(s,3H), 1.95–1.59(m,4H), 1.43(s,9H), 1.41(s,9H). 13 C NMR (100MHz, CDCl 3 )δ171.7, 164.5, 155.5, 134.6, 130.1, 129.0, 126.7, 82.0, 79.6, 53.7, 47.8, 30.2, 28.4, 28.0, 23.2, 20.4.

[0018] Synthesis of compound i-3

[0019] Compound i-2 (3.38g, 7.50mmol, 1.0equiv) was dissolved in trifluo...

Embodiment 2

[0032]

[0033] Synthesis of compound ii-2

[0034] The raw material triphenylphosphine (15.3g, 58.4mmol, 2.2equiv) was dissolved in THF (100mL), at 0°C, DIAD (11.6mL, 58.4mmol, 2.2equiv) was added, and after 30 minutes of reaction, ii-1( 5.00g, 26.6mmol, 1.0equiv), and after another 10 minutes, slowly add thioacetic acid (4.1mL, 58.4mmol, 2.2equiv) in tetrahydrofuran (20mL) solution, react for 4 hours, spin dry, pass through a silica gel column to obtain the compound ii-2 (89%, 5.82g). 1 H NMR (400MHz, CDCl 3 )δ4.81(s,2H),4.57–4.48(m,1H),3.34(dd,J=13.9,7.4Hz,1H),3.26(dd,J=13.9,6.7Hz,1H),2.38(s ,3H),1.48(s,3H),1.40(s,3H). 13 C NMR (100MHz, CDCl 3 )δ195.1, 173.3, 114.4, 77.5, 76.4, 76.3, 30.6, 27.9 26.8, 26.0.

[0035] Synthesis of compound ii-3

[0036] Compound ii-2 (5.0 g, 20.3 mmol, 1.0 equiv) dichloromethane (40 mL) was added to trifluoroacetic acid (8 mL) and water (1.8 mL) in sequence. After reacting for 5 hours, it was spin-dried and passed through a silica ge...

Embodiment 3

[0056]

[0057] Synthesis of compound iii-1

[0058] Compound ii-9 (355mg, 0.95mmol, 1.0equiv) was dissolved in acetonitrile (6mL), and imidazole (142mg, 2.09mmol, 2.2equiv) and TBSCl (315mg, 2.09mmol, 2.2equiv) were added successively, and reacted for 2 hours, It was quenched with water, extracted, spin-dried, and passed through a silica gel column to obtain compound iii-1 (454 mg, 98%). 1 H NMR (400MHz, CDCl 3 )δ8.69(brs,1H),8.22(d,J=8.2Hz,1H),6.15(d,J=8.9Hz,1H),5.77(d,J=8.1Hz,1H),4.49(t, J=9.7Hz, 1H), 4.19(dd, J=10.2, 7.8Hz, 1H), 4.14(dd, J=10.9, 2.1Hz, 1H), 3.76(dd, J=10.9, 2.6Hz, 1H), 3.40–3.34(m,1H),3.24(s,3H),3.06(s,3H),1.27(s,6H),0.96(s,9H),0.17(s,3H),0.15(s,3H) . 13 C NMR (100MHz, CDCl 3 )δ163.3, 151.0, 141.3, 103.3, 100.6, 100.4, 73.5, 69.7, 62.5, 56.9, 48.1, 47.8, 46.6, 26.2, 18.9, 17.9, 17.7, -5.1, -5.5.

[0059] Synthesis of compound iii-2

[0060]Compound iii-1 (317mg, 0.65mmol, 1.0equiv), triethylamine (180μL, 1.30mmol, 2.0equiv), DMAP (159mg, 1.30mmol...

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Abstract

The invention relates to a method for synthesizing albomycin delta 1, albomycin delta 2 and albomycin epsilon, and application of the albomycin delta 1, the albomycin delta 2 and the albomycin epsilonas antibacterial drugs. According to the synthesis method, a Mitsunobu reaction, a Pummerer rearrangement, and an aldol reaction are utilized to complete complete synthesis of the albomycin delta 1,the albomycin delta 2 and the albomycin epsilon. The synthesis method is easy to operate, mild in reaction condition, low in cost and high in yield. The albomycin delta 1, the albomycin delta 2 and the albomycin epsilon obtained through synthesis have different degrees of inhibitory activity to streptococcus pneumoniae, staphylococcus aureus, bacillus subtilis, escherichia coli, gonococcus and thelike, and can be applied as the antimicrobial drugs.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and medicinal chemistry, and relates to the natural product albomycinδ 1 ,δ 2 The synthetic method of and ε and the application of these compounds as antibacterial drugs. Background technique [0002] Since Fleming discovered penicillin in the late 1920s and was widely used in the treatment of infectious diseases during World War II, antibiotics have saved the lives of countless infectious patients in the past 70 years and increased the average human life expectancy by 15-20. year. However, the widespread use of antibiotics, especially the problem of bacterial resistance caused by the abuse of antibiotics has become the most difficult problem in the treatment of clinical bacterial infections. The frequent emergence and spread of multidrug-resistant bacteria and even "super bacteria" have posed a new threat to human health. At the same time, only a few antibacterial drugs have been ap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/06A61K38/08A61P31/04
CPCA61K38/00A61P31/04C07K7/06Y02A50/30Y02P20/55
Inventor 贺耘林子华徐小波赵胜杨晓洪
Owner CHONGQING UNIV
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