(S)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol | 1548042-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol
• 英文别名: (1S)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol
• CAS: 1548042-26-7
• 化学式: C₁₀H₁₃BrO₃
• 分子量: 261.115
• InChiKey: WOCOYNIOMURNJZ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 对甲苯磺酸 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 66.0h， 生成 (S)-5-(4-ethynylphenyl)-1,4-dioxan-2-one
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of benzyloxyacetohydroxamic acids as LpxC inhibitors

  摘要：

  The inhibition of the UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) represents a promising strategy to combat infections caused by multidrug-resistant Gram-negative bacteria. In order to elucidate the functional groups being important for the inhibition of LpxC, the structure of our previously reported hydroxamic acid 4 should be systematically varied. Therefore, a series of benzyloxyacetohydroxamic acids was prepared, of which the diphenylacetylene derivatives 28 (K-i = 95 nM) and 21 (K-i = 66 nM) were the most potent inhibitors of Escherichia coli LpxC. These compounds could be synthesized in a stereoselective manner employing a Sharpless asymmetric dihydroxylation and a Sonogashira coupling in the key steps. The obtained structure-activity relationships could be rationalized by molecular docking studies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.057
• 作为产物：
  描述：

  对溴苯乙烯 在 AD-mix-α 、 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 32.0h， 生成 (S)-1-(4-bromophenyl)-2-(methoxymethoxy)ethanol
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of benzyloxyacetohydroxamic acids as LpxC inhibitors

  摘要：

  The inhibition of the UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) represents a promising strategy to combat infections caused by multidrug-resistant Gram-negative bacteria. In order to elucidate the functional groups being important for the inhibition of LpxC, the structure of our previously reported hydroxamic acid 4 should be systematically varied. Therefore, a series of benzyloxyacetohydroxamic acids was prepared, of which the diphenylacetylene derivatives 28 (K-i = 95 nM) and 21 (K-i = 66 nM) were the most potent inhibitors of Escherichia coli LpxC. These compounds could be synthesized in a stereoselective manner employing a Sharpless asymmetric dihydroxylation and a Sonogashira coupling in the key steps. The obtained structure-activity relationships could be rationalized by molecular docking studies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.057

文献信息

• Phenylethylene glycol-derived LpxC inhibitors with diverse Zn2+-binding groups
  作者：Magdalena Galster、Marius Löppenberg、Fabian Galla、Frederik Börgel、Oriana Agoglitta、Johannes Kirchmair、Ralph Holl

  DOI：10.1016/j.tet.2018.12.011

  日期：2019.1

  hydroxamate moiety by other Zn2+-binding groups while maintaining target activity. In total, 15 phenylethylene glycol derivatives with diverse Zn2+-binding groups like carboxylate, hydrazide, carboxamide, sulfonamide, vicinal diol, thiol, thioester, and hydroxypyridinone moieties were prepared in divergent syntheses. However, their biological evaluation revealed that the replacement of the hydroxamate

  依赖于Zn 2+的细菌脱乙酰基酶LpxC是开发新型抗生素的有希望的目标。大多数已知的LpxC抑制剂带有异羟肟酸酯部分作为Zn 2+结合基团。但是，异羟肟酸通常显示出不良的药代动力学性质。（小号） - ñ -羟基-2- 2-羟基-1- [4-（苯基乙炔基）苯基]乙氧基}乙酰胺（3）是有效地抑制LpxC用K已知苯基亚乙基二醇衍生物我的66纳米。体外实验已在计算机模拟中证实了3的异羟肟酸酯部分确实在代谢上不稳定。在这项研究中，探索了几种策略来用其他Zn 2+结合基团取代异羟肟酸酯部分，同时保持靶标活性。总共以不同的合成方法制备了具有不同的Zn 2+结合基团的15种苯基乙二醇衍生物，例如羧酸根，酰肼，羧酰胺，磺酰胺，邻二醇，硫醇，硫代酯和羟基吡啶酮部分。然而，他们的生物学评估表明，被研究的任何Zn 2+结合基团取代3的异羟肟酸酯部分对LpxC的抑制和抗菌活性都是有害的。