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Thiazole orange styrene derivative, method for preparing same and application of thiazole orange styrene derivative to preparing medicines capable of resisting medicine-resistant bacteria

A technology for thiazole orange styrene and derivatives, which is applied in the field of new pharmaceutical compounds and achieves the effects of cheap raw materials, simple preparation method and significant inhibitory effect

Active Publication Date: 2016-12-07
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of anti-drug-resistant bacteria drugs based on thiazole orange styrene derivatives has not been reported in the literature

Method used

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  • Thiazole orange styrene derivative, method for preparing same and application of thiazole orange styrene derivative to preparing medicines capable of resisting medicine-resistant bacteria
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  • Thiazole orange styrene derivative, method for preparing same and application of thiazole orange styrene derivative to preparing medicines capable of resisting medicine-resistant bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Synthesis of Thiazole Orange Styrene Derivatives

[0030] Weigh out 0.15mmol In a 25ml round-bottomed flask, add 0.30mmol p-hydroxybenzaldehyde, 1.5ml n-butanol and 5 drops of 4-methylpiperidine, react at 130-135°C for 3 hours, cool to room temperature, and collect the crude product by suction filtration. Recrystallization of n-butanol to obtain a purple-black solid powder compound is a thiazole orange styrene derivative, and its chemical structural formula is as shown in formula (II):

[0031]

[0032] Yield 88%; 1 H NMR (400MHz, DMSO) δ8.59 (t, J = 17.8Hz, 1H), 8.04–7.82 (m, 3H), 7.79–7.60 (m, 3H), 7.49 (d, J = 22.2Hz, 3H) ,7.36(t,J=18.0Hz,3H),6.87(d,J=7.9Hz,2H),6.68(s,1H),3.98(d,J=22.1Hz,3H),3.83(s,3H) .13CNMR(100MHz,DMSO)δ160.39(s), 159.11(s), 152.57(s), 147.55(s), 141.65(s), 140.78(s), 139.26(s), 133.45(s), 131.04 (s), 128.37(s), 126.71(s), 125.49(s), 124.38(s), 124.09(s), 123.73(s), 123.32(s), 118.79(s), 117.93(s), 116.25 (s), 112.79(s), 107.92...

Embodiment 2

[0033] Example 2: Synthesis of Thiazole Orange Styrene Derivatives

[0034] The preparation method of this embodiment except using Except for replacing p-hydroxybenzaldehyde, all the other are the same as in Example 1. Finally, the purple-red solid powder compound is a thiazole orange styrene derivative, and its chemical structural formula is as shown in formula (Ⅲ):

[0035]

[0036] Yield 83%; 1 H NMR (400MHz, DMSO) δ8.72(d, J=8.4Hz, 1H), 8.24(d, J=8.68Hz, 1H), 8.08(d, 1H), 8.02(d, J=7.4Hz, 3H ),7.84(d,J=4.5Hz,1H),7.75(m,J=9.5Hz,3H),7.65(s,1H),7.56(s,3H),7.45(t,J=8.3Hz,1H ),6.95(s,1H),4.27(s,3H),4.02(s,3H). 13CNMR (100MHz, DMSO) δ159.57(s), 154.63(s), 148.40(s), 140.95(s), 139.64(s), 139.49(s), 133.58(s), 130.62(s), 129.43( s), 128.50(s), 126.83(s), 125.82(s), 124.67(s), 124.14(s), 123.91(s), 123.48(s), 123.17(s), 118.73(s), 113.10( s), 111.03(s), 87.33(s), 37.56(s), 34.09(s).ESI-MS: [M–I] + (C 27 h 22 ClN 2 S + ): theoretical value m / z 441.1, actual value: m / z...

Embodiment 3

[0037] Example 3: Synthesis of Thiazole Orange Styrene Derivatives

[0038] The preparation method of this embodiment except using Except for replacing p-Hydroxybenzaldehyde, all the other are the same as in Example 1. Finally, the reddish-brown solid powder compound is a thiazole orange styrene derivative, and its chemical structural formula is as shown in formula (IV):

[0039]

[0040] Yield 85%; 1 H NMR (400MHz, DMSO) δ8.69 (d, J = 8.4Hz, 1H), 8.01 (dd, J = 29.3, 10.1Hz, 4H), 7.94–7.89 (m, 1H), 7.70 (d, J = 7.6Hz, 1H), 7.63(dd, J=19.6, 11.2Hz, 3H), 7.54(d, J=14.5Hz, 1H), 7.44(s, 1H), 7.34(dd, J=19.2, 8.3Hz, 3H), 6.79(s,1H), 4.07(s,3H), 3.92(s,3H). 13 C NMR (100MHz, DMSO) δ159.83(s), 152.07(s), 148.00(s), 140.82(s), 139.79(s), 139.32(s), 133.66(s), 132.22(s), 131.24 (s), 131.16(s), 128.49(s), 126.90(s), 125.61(s), 124.66(s), 124.27(s), 123.85(s), 123.42(s), 121.96(s), 118.89 (s), 116.47(s), 116.25(s), 113.09(s), 108.23(s), 88.29(s), 38.53(s), 34.13(s).ESI-MS: [MI] ...

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Abstract

The invention belongs to the field of novel medicines and compounds, and discloses a thiazole orange styrene derivative, a method for preparing the same and application of the thiazole orange styrene derivative to preparing medicines capable of resisting medicine-resistant bacteria. The thiazole orange styrene derivative is of a structure shown as a formula (I). An R in the formula is defined as an instruction book. The method includes carrying out condensation reaction on thiazole orange analogues and different types of aromatic aldehyde to obtain the thiazole orange styrene derivative. The thiazole orange styrene derivative, the method and the application have the advantages that the method is simple, and raw materials for the thiazole orange styrene derivative are easily available; excellent interaction between the thiazole orange styrene derivative and bacterium division proteins FtsZ can be realized, and accordingly reproduction of diversified medicine-resistant bacteria such as vancomycin-resistant enterococci and methicillin-resistant staphylococcus aureus can be inhibited; the thiazole orange styrene derivative is little in toxic and side effect and has a prospect of being developed to obtain novel antibiotic medicines.

Description

technical field [0001] The invention belongs to the field of new drug compounds, and in particular relates to a thiazole orange styrene derivative, a preparation method thereof and an application in preparation of anti-drug-resistant bacteria drugs. Background technique [0002] The widespread use (especially abuse) of antibiotics has led to the increasing resistance of bacteria to antibiotics, such as new drug-resistant bacteria (commonly known as "superbugs") methicillin-resistant Staphylococcus aureus (MRSA), multidrug-resistant aureus Staphylococcus (MDRSA) and vancomycin-resistant enterococcus (VRE) have appeared one after another, and there is an epidemic trend. Currently, commonly used antimicrobial drugs are almost ineffective against drug-resistant bacteria, leading to an increase in the mortality rate of patients year by year. Therefore, it is urgent to develop new drugs against drug-resistant bacteria. At present, some new drugs, such as oxazolidinones, daptomyci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C07D417/14A61K31/4439A61K31/444A61P31/04
CPCC07D417/06C07D417/14Y02A50/30
Inventor 卢宇靖郑园园孙宁张焜黄宝华
Owner GUANGDONG UNIV OF TECH
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