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Palymycin analogue and its preparation method and application

A technology of platymycin and analogues, which is applied in antibacterial drugs, organic chemistry, etc., can solve the problems of not obtaining biological activity, etc., and achieve the effects of improving raw material utilization, simple operation, and low cost

Active Publication Date: 2021-06-11
CHANGSHA CHARISM BIOSCIENCES CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, none of the existing synthetic platymycin analogues have achieved the desired biological activity

Method used

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  • Palymycin analogue and its preparation method and application
  • Palymycin analogue and its preparation method and application
  • Palymycin analogue and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1: Take platymycin (0.20 mmol), put it into a reaction bottle, add 7.0 ml of pure water, stir at room temperature for 5 minutes, and place it at -10°C. Weigh concentrated sulfuric acid (0.10mmol) and dissolve it in pure water, slowly add it dropwise to the reaction system, heat up to 80°C and stir for 12 hours, then remove the solvent by rotary evaporation to obtain a crude product; then pass through column chromatography (eluent: petroleum Ether: ethyl acetate = 1:20 ~ 1:5) was isolated to obtain platymycin acid PTMA-1 with a yield of 90%.

[0051] The structural formula of the product PTMA-1 is:

[0052] PTMA-1 is characterized by: 1 H NMR (500MHz, CDCl 3 )δ6.46(d, J=10.1Hz, 1H), 5.88(d, J=10.1Hz, 1H), 4.42(s, 1H), 2.41(t, J=6.5Hz, 1H), 2.38–2.31( m,2H),2.31–2.21(m,2H),2.13–2.05(m,1H),2.05–1.96(m,2H),1.87(dd,J=11.2,3.5Hz,1H),1.81–1.68( m, 2H), 1.60(d, J=11.2Hz, 1H), 1.44(s, 3H), 1.22(s, 3H);

[0053] 13 C NMR (101MHz, CDCl 3 )δ203.30, 177.62, 153.57, ...

Embodiment 2

[0055] Example 2: Weighed platymycin (0.20 mmol), put it into a reaction bottle, added 7.0 ml of methanol, stirred at room temperature for 5 minutes, and placed it at -10°C. Weigh concentrated sulfuric acid (0.10mmol) and dissolve it in methanol, slowly add it dropwise to the reaction system, heat up to 80°C and stir for 12 hours, then remove the solvent by rotary evaporation to obtain a crude product; then pass through column chromatography (eluent: petroleum ether : Ethyl acetate=1:20~1:5) separated to obtain platymycin acid PTMA-2 with a yield of 95%.

[0056] The structural formula of the product PTMA-2 is:

[0057] PTMA-2 is characterized by: 1 H NMR (500MHz, CDCl 3 )δ6.43(d, J=10.1Hz, 1H), 5.83(d, J=10.1Hz, 1H), 4.34(s, 1H), 3.60(s, 3H), 2.36(t, J=6.5Hz, 1H),2.32–2.13(m,5H),2.03(d,J=5.3Hz, 1H),2.00–1.91(m,3H),1.81(dd,J=11.1,3.4Hz,1H),1.70(ddd ,J=19.0,12.8,8.2Hz,3H), 1.57(d,J=11.1Hz,1H),1.39(s,3H),1.18(s,3H);

[0058] 13 C NMR (101MHz, CDCl 3 )δ203.21, 173.74, 15...

Embodiment 3

[0060] Example 3: Take platymycin (0.20 mmol), put it into a reaction bottle, add 7.0 ml of ethanol, stir at room temperature for 5 minutes, and place it at -10°C. Weigh concentrated sulfuric acid (0.10mmol) and dissolve it in ethanol, slowly add it dropwise to the reaction system, heat up to 80°C and stir for 12 hours, then remove the solvent by rotary evaporation to obtain a crude product; then pass through column chromatography (eluent: petroleum ether : Ethyl acetate=1:20~1:5) separated to obtain platymycin acid PTMA-3 with a yield of 95%.

[0061] The structural formula of the product PTMA-3 is:

[0062] PTMA-3 is characterized by: 1 H NMR (400MHz, CDCl 3 )δ6.43(d, J=10.1Hz, 1H), 5.84(d, J=10.1Hz, 1H), 4.35(s, 1H), 4.10–4.05(m, 2H), 2.37(t, J=6.5 Hz,1H),2.32(s,1H),2.30–2.11(m,3H), 2.03(dd,J=6.3,5.3Hz,1H),1.99–1.94(m,2H),1.81(dd,J= 11.1,3.6Hz,1H),1.77–1.64(m,2H),1.61–1.54(m,1H),1.40(s,3H),1.19(s,3H),1.19(dd,J=6.3,3.2Hz ,3H);

[0063] 13 C NMR (101MHz, CDCl 3 )δ20...

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Abstract

The present invention relates to a kind of flat mycin analogue and its preparation method and application, by taking flatmycin as raw material, taking acid as catalyst, using water and / or alcohol as solvent, through heating reaction to obtain flatmycin acid analogue of the present invention things. The invention has short preparation route, safe and simple operation, is convenient for obtaining platymycin analogues, provides diverse compound skeletons, and can be widely used in the fields of new drug screening and pharmacy.

Description

technical field [0001] The invention relates to a platymycin analogue and its preparation method and application, belonging to the technical field of new drug synthesis. Background technique [0002] Drug-resistant pathogenic bacteria infection and diabetes are major diseases that seriously endanger human health. In recent years, with the widespread and increasing clinical application of antibiotics, problems such as bacterial resistance, adverse reactions, and double infections due to irrational abuse have become increasingly serious, leading to failure of anti-infective treatment, resulting in morbidity and mortality The increase in medical expenses and the increase in medical expenses have brought many difficulties to clinical treatment and posed a great threat to human health. There are more and more drug-resistant bacteria, and the range of drug resistance is getting wider and higher. Bacterial drug resistance has become a serious problem in the field of anti-infection...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94C08G65/334A61P31/04
CPCC07D493/10C08G65/3348
Inventor 段燕文沈奔黄勇朱湘成邱林田凯
Owner CHANGSHA CHARISM BIOSCIENCES CO LTD
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