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Carbon 2-bit substituted cephalosporin derivative as well as synthetic method and application thereof

A kind of technology of cephalosporins and derivatives, applied in the field of drug synthesis

Inactive Publication Date: 2010-03-17
天津市医药集团技术发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But since the discovery of human leukocyte trypsin and β-lactamase inhibitors, this situation has changed greatly

Method used

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  • Carbon 2-bit substituted cephalosporin derivative as well as synthetic method and application thereof
  • Carbon 2-bit substituted cephalosporin derivative as well as synthetic method and application thereof
  • Carbon 2-bit substituted cephalosporin derivative as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Synthesis of 7-formylamino-3-(1-methyltetrazolyl-5-mercaptomethyl)-ceph-3-ene-4-carboxylic acid p-methoxybenzyl ester II-1:

[0121]

[0122] Add methylmercaptotetrazolium (3.250g, 28mmol) and 150mL of dichloromethane into the reaction flask, add triethylamine (3.65mL, 28.7mmol) dropwise, and then add formyl (10.012g, 25.2mmol) , After reacting for 4 hours, 11.661 g of white solid was obtained by filtration, and the yield was 97.1%.

Embodiment 2

[0124] Synthesis of 7-formylamino-3-(1-methyltetrazolyl-5-mercaptomethyl)-ceph-3-ene-4-carboxylic acid p-methoxybenzyl ester-1-sulfoxide (III -1):

[0125]

[0126] Add compound (II-1) (9.526g, 20mmol) and 120mL toluene into the reaction flask, add acetic anhydride (21.32mL, 226mmol) and hydrogen peroxide (30%) (10.66mL, 104mmol) under ice-bath conditions, 2h After the reaction was basically completed, saturated sodium bicarbonate solution and sodium bisulfite solution were added to neutralize excess acetic anhydride and hydrogen peroxide, and 8.985 g of white solid was obtained by filtration, with a yield of 91.26%.

Embodiment 3

[0128] 7-Formylamino-3-(1-methyltetrazolyl-5-mercaptomethyl)-2-methylene-ceph-3-ene-4-carboxylic acid p-methoxybenzyl ester-1- Synthesis of sulfoxide (A):

[0129] Compound (III-1) (4.920g, 10mmol), diethylamine (2.05mL, 20mmol), trifluoroacetic acid (1.48mL, 20mmol), formaldehyde (37%) (1.90mL, 20mmol), 11.86mL tert-butyl Alcohol and 45mL of 1,4-dioxane were reacted at 50-53°C for 2h, then the reaction liquid was dropped into 400mL of water, and filtered to obtain 4.526g of khaki solid with a yield of 89.80%.

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Abstract

The invention relates to a carbon 2-bit substituted cephalosporin derivative as well as a synthetic method and application thereof. The synthetic method comprises the following steps: carrying out Mannich condensation by taking GCLE and derivatives thereof as raw materials to introduce double bonds and a methylation reaction, carrying out Michael addition reaction based on the Manich condensationto modify cephalosporin mother nucleus 2-bit, thereby acquiring a series of compounds. The acquired target compounds have a certain antibacterial activity to gram-positive bacteria, wherein two compounds with the form of sulphoxide in 1-bit also present stronger combination ability with beta-lactamase.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and relates to substituted cephalosporin derivatives, in particular to a new class of carbon 2-substituted cephalosporin derivatives with antibacterial activity and β-lactamase inhibitory ability and its synthesis method and application. Background technique [0002] Cephalosporins are a class of broad-spectrum semi-synthetic antibiotics that emerged in the mid-1960s and reached their peak in the 1980s. A total of more than 50,000 species were synthesized, and more than 50 semi-synthetic cephalosporins with broad spectrum, high efficiency, long-acting and enzyme resistance were obtained. In the anti-infection treatment, cephalosporins are widely used in clinic due to their advantages such as broad bacterial spectrum, strong antibacterial activity, acid resistance, enzyme resistance, high curative effect, and relatively small toxic and side effects, and have made great contributions to hum...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/04A61K31/546A61P31/04
Inventor 孟红赵平王亚江李玉荃刘晓
Owner 天津市医药集团技术发展有限公司
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