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首页> 外文期刊>Acta crystallographica. Section C, Structural chemistry. >Conformational study of ( Z Z )‐5‐(4‐chlorobenzylidene)‐2‐[4‐(2‐hydroxyethyl)piperazin‐1‐yl]‐3 H H ‐imidazol‐4(5 H H )‐one in different environments: insight into the structural properties of bacterial efflux pump inhibitors
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Conformational study of ( Z Z )‐5‐(4‐chlorobenzylidene)‐2‐[4‐(2‐hydroxyethyl)piperazin‐1‐yl]‐3 H H ‐imidazol‐4(5 H H )‐one in different environments: insight into the structural properties of bacterial efflux pump inhibitors

机译：（ZZ）-5-（4-氯苄基）-2- [4-（2-羟乙基）哌嗪-1-基] -3 HH-HH-inimidazol-4（5 hH）-4（5 hh） - 洞中的（ZZ）-5-（4-氯苯基）-2- [4-（2-羟基乙基）-3] - 洞察力 细菌渗透泵抑制剂的结构性能

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摘要

The 2‐amine derivatives of 5‐arylidene‐3 H ‐imidazol‐4(5 H )‐one are a new class of bacterial efflux pump inhibitors, the chemical compounds that are able to restore antibiotic efficacy against multidrug resistant bacteria. 5‐Arylidene‐3 H ‐imidazol‐4(5 H )‐ones with a piperazine ring at position 2 reverse the mechanisms of multidrug resistance (MDR) of the particularly dangerous Gram‐negative bacteria E. coli by inhibition of the efflux pump AcrA/AcrB/TolC (a main multidrug resistance mechanism in Gram‐negative bacteria, consisting of a membrane fusion protein, AcrA, a Resistant‐Nodulation‐Division protein, AcrB, and an outer membrane factor, TolC). In order to study the influence of the environment on the conformation of ( Z )‐5‐(4‐chlorobenzylidene)‐2‐[4‐(2‐hydroxyethyl)piperazin‐1‐yl]‐3 H ‐imidazol‐4(5 H )‐one, ( 3 ), two different salts were prepared, namely with picolinic acid {systematic name: 4‐[( Z )‐4‐(4‐chlorobenzylidene)‐5‐oxo‐3,4‐dihydro‐1 H ‐imidazol‐2‐yl]‐1‐(2‐hydroxyethyl)piperazin‐1‐ium pyridine‐2‐carboxylate, C 16 H 20 ClN 4 O 2 + ·C 6 H 4 NO 2 ? , ( 3 a )} and 4‐nitrophenylacetic acid {systematic name: 4‐[( Z )‐4‐(4‐chlorobenzylidene)‐5‐oxo‐3,4‐dihydro‐1 H ‐imidazol‐2‐yl]‐1‐(2‐hydroxyethyl)piperazin‐1‐ium 2‐(4‐nitrophenyl)acetate, C 16 H 20 ClN 4 O 2 + ·C 8 H 6 NO 4 ? , ( 3 b )}. The crystal structures of the new salts were determined by X‐ray diffraction. In both crystal structures, the molecule of ( 3 ) is protonated at an N atom of the piperazine ring by proton transfer from the corresponding acid. The carboxylate group of picolinate engages in hydrogen bonds with three molecules of the cation of ( 3 ), whereas the carboxylate group of 4‐nitrophenylacetate engages in hydrogen bonds with only two molecules of ( 3 ). As a consequence of these interactions, different orientations of the hydroxyethyl group of ( 3 ) are observed. The crystal structures are additionally stabilized by both C—H…N [in ( 3 a )] and C—H…O [in ( 3 a ) and ( 3 b )] intermolecular interactions. The geometry of the imidazolone fragment was compared with other crystal structures possessing this moiety. The tautomer observed in the crystal structures presented here, namely 3 H ‐imidazol‐4(5 H )‐one [systematic name: 1 H ‐imidazol‐5(4 H )‐one], is also that most frequently observed in other structures containing this heterocycle.
机译：5-亚亚亚胺-3 H-inimidazol-4（5h）的2-胺衍生物是一种新的细菌渗透泵抑制剂，能够恢复抗生素抗性细菌的抗生素功效的化学化合物。 5-亚亚胺-3H-inimidazol-4（5h） - 具有哌嗪环的哌嗪环，在第2位，通过抑制Efflux泵Acra来逆转特别危险的革兰氏阴性细菌大肠杆菌的多药耐药性（MDR）的机制/ ACRB / TOLC（革兰氏阴性细菌的主要多药电阻机制，由膜融合蛋白，ACRA，抗性衍生分裂蛋白，ACRB和外膜因子TOLC）组成。为了研究环境对（Z）-5-（4-氯苄基）-2- [4-（2-羟基乙基）哌嗪-1-基] -3H-inimidazol-4的构象的影响 - 3（5 h） - （3），制备两种不同的盐，即用氨鼻乙酸{系统名称：4 - [（Z）-4-（4-氯苄基）-5-氧代-3,4-二氢-1H -imidazol-2-y1] -1-（2-羟乙基）哌嗪-1-10吡啶-2-羧酸盐，C 16 H 20 ClN 4 O 2 +·C 6 H 4 NO 2？ ，（3 a）}和4-硝基苯基乙酸{系统名称：4 - [（z）-4-（4-氯苄基）-5-氧代-3,4-二氢-1h-inimidazol-2-yl] - 1-（2-羟乙基）哌嗪-1-1-Ium 2-（4-硝基苯基）乙酸盐，C 16 H 20 ClN 4 O 2 +·C 8 H 6 NO 4？ ，（3 b）}。通过X射线衍射测定新盐的晶体结构。在两个晶体结构中，（3）的分子通过来自相应酸的质子转移在哌嗪环的n原子处质子化。甲基酯的羧酸酯基团与（3）的阳离子的三个分子啮合，而4-硝基苯乙酸酯的羧酸盐基团在氢键中，只有两个分子（3）。由于这些相互作用的结果，观察到（3）的羟乙基的不同取向。通过C-H ... n [in（3a）]和c-h ... o [in（3a）和（3b）]分子间相互作用另外稳定晶体结构。将咪唑酮片段的几何形状与具有该部分的其他晶体结构进行比较。在此处呈现的晶体结构中观察到的互变异构体，即3 H-inimidazol-4（5h） - One [系统名称：1 H-Himidazol-5（4h） - One]，也是在其他结构中最常观察到的含有这种杂环。

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