A kind of dihydrooxazole antibiotic and preparation method thereof

A technology of dihydrooxazoles and antibiotics, applied in the field of antibiotics, can solve the problem of no antibacterial activity and the like, and achieve the effect of high inhibitory activity

Inactive Publication Date: 2016-03-09
日照市甲子山茶业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

People such as YukiInahashi in Japan and WeimingZhu in China obtained compound (II) (R)-2-(o-hydroxyphenyl)-4-hydroxymethyl-4,5 from Streptosporangium oxazolinicum K07-0460T and NocardiopsisdassonvilleiHR10-5 fermentation products respectively -dihydrooxazoles, but none have antibacterial activity

Method used

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  • A kind of dihydrooxazole antibiotic and preparation method thereof
  • A kind of dihydrooxazole antibiotic and preparation method thereof
  • A kind of dihydrooxazole antibiotic and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Fermentation of Antibiotics

[0043] Step 1: Fermentation

[0044] (1) Fermentation strain: The fermentation strain was obtained from soil samples collected from pesticide-contaminated areas in Shandong Peninsula, China, isolated and cultivated in the laboratory, and identified as Streptomyces djakartensis; Deposited by the center, the deposit date is November 13, 2012, and the deposit registration number is CGMCCNo.6817;

[0045] (2) Slant culture: use starch casein culture based on 1×10 5 Sterilize under handkerchief for 30 minutes, culture at 28°C for 5 days after inoculation; the starch casein medium is composed of the following components: 10.0 g of soluble starch, 2.0 g of dipotassium hydrogen phosphate, 2.0 g of potassium nitrate, 2.0 g of sodium chloride, 0.3g casein, 0.05g magnesium sulfate heptahydrate, 0.02g calcium carbonate, 0.01g ferrous sulfate heptahydrate, 20.0g agar, 1000ml distilled water, pH value 7.2;

[0046] (3) Seed culture: subpackage the see...

Embodiment 2

[0066] Antibiotics of chemical synthesis preparation formula (I)

[0067] Add 119mg (1mmol) of o-hydroxybenzocyanide and 30ml of anhydrous methanol to a 50ml dry round bottom flask, dissolve under electromagnetic stirring, add 5ml of acetyl chloride dropwise, stir and react at room temperature for 24h, then add 10ml of triethylamine and 91mg ( 1mmol) serinol, reflux reaction 12h. The reaction solution was poured into 200 ml of ethyl acetate, and washed with 20 ml of water and 20 ml of saturated brine. Dry over anhydrous sodium sulfate and remove the solvent. It was separated by column chromatography and recrystallized from acetone to obtain 116 mg of colorless crystals. The colorless crystalline 1 H-NMR and 13 C-NMR confirms that the structure is an antibiotic shown in formula (I). 1 HNMR (CDCl 3 , 500MHz, δ, ppm): 3.74 (dd, 1H, J = 3.5Hz, 11.5Hz), 3.92 (dd, 1H, J = 3.5Hz, 11.5Hz), 4.34-4.38 (m, 1H), 4.45-4.49 (m, 1H), 4.50-4.52 (m, 1H), 6.84 (1H, m), 6.97 (1H, d, J=8.0...

Embodiment 3

[0069] The bacteriostatic activity of the antibiotic of formula (I) of the present invention

[0070] Adopt microdilution method to measure the antibiotic of formula (I) of the present invention to bacillus cereus (Bacillus cereus), bacillus subtilis (B.subtilis), staphylococcus aureus (Staphylococcus aureus), Escherichia coli (Escherichiacoil), methoxy-resistant The antibacterial activity of 8 kinds of tested bacteria including Staphylococcus aureus (Methicillin-resistant Staphylococcusaureus, MRSA), soft rot fungus of cabbage (Erwinacarotovora), fungus of kiwi fruit canker (Pseudomonassyringae Pv.actinidiae), and Xanthomonasoryzae. Except for methicillin-resistant Staphylococcus aureus, which was provided by Nanjing Medical University, the rest of the strains were purchased from China General Microorganisms Collection Center.

[0071] Pick 4-5 common test colonies with the same shape from the culture plate with an inoculation loop, insert them into Mueller-Hinton broth mediu...

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Abstract

The invention relates to a dihydrooxazole antibiotic with a chemical formula of C10H11NO3. The chemical structural formula of the dihydrooxazole antibiotic is shown in a formula (I) which is described in the specification. The invention further relates to a biosynthetic method and two chemical synthetic methods for the compound, i.e., dihydrooxazole antibiotic. Moreover, the invention also relates to application of the compound in inhibition of a plurality of human and animal pathogenic bacteria and crop pathogenic bacteria. The compound is a novel compound having not been reported at home and abroad and has a brand new molecular structure. The compound can be prepared both through microbial fermentation and artificial chemical synthesis.

Description

technical field [0001] The invention belongs to the field of antibiotics, and in particular relates to an antibiotic and a preparation method thereof. technical background [0002] Whether it is the pharmaceutical industry or the pesticide industry, there is an urgent need to screen and develop new antibiotics. People such as YukiInahashi in Japan and WeimingZhu in China obtained compound (II) (R)-2-(o-hydroxyphenyl)-4-hydroxymethyl-4,5 from Streptosporangium oxazolinicum K07-0460T and NocardiopsisdassonvilleiHR10-5 fermentation products respectively -dihydrooxazoles, but none have antibacterial activity. In 2013, Wu Wenjun and others applied for a national invention patent "a benzoazepam antibiotic and its production method" (patent application number 201310028444.1), which described the isolation of an antibiotic from the fermentation product of Streptomyces djakartensis 2 -Hydroxymethyl-3,4-dihydro-1,4-benzazepine-5 (1H) ketone (III); the structural formula of the compo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/14C12P17/14A61P31/04A01P1/00A01P3/00C12R1/465
CPCC07D263/14C12P17/14
Inventor 吴文君张继文
Owner 日照市甲子山茶业有限公司
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