Ethylphosphonic acid 4-nitrophenyl ester | 368874-04-8

• 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: Ethylphosphonic acid 4-nitrophenyl ester
• 英文别名: ethyl-(4-nitrophenoxy)phosphinic acid
• CAS: 368874-04-8
• 化学式: C₈H₁₀NO₅P
• 分子量: 231.145
• InChiKey: BBUVBGGUNXIOMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethylphosphonic acid 4-nitrophenyl ester 在 劳森试剂 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 27.0h， 生成 2-Bromoethoxy-ethyl-(4-nitrophenoxy)-sulfanylidene-lambda5-phosphane
  参考文献：
  名称：

  Synthesis and anti-acetylcholinesterase properties of novel β- and γ-substituted alkoxy organophosphonates

  摘要：

  Activated organophosphate (OP) insecticides and chemical agents inhibit acetylcholinesterase (AChE) to form OP-AChE adducts. Whereas the structure of the OP correlates with the rate of inhibition, the structure of the OP-AChE adduct influences the rate at which post-inhibitory reactivation or aging phenomena occurs. In this report, we prepared a panel of beta-substituted ethoxy and gamma-substituted propoxy phosphonoesters of the type p-NO2PhO-P(X)(R)[(O(CH2)(n)Z] (R = Me, Et; X = O, S; n = 2, 3; Z = halogen, OTs) and examined the inhibition of three AChEs by select structures in the panel. The beta-fluoroethoxy methylphosphonate analog (R = Me, Z = F, n = 2) was the most potent anti-AChE compound comparable (k(i); similar to 6 x 10(6) M-1 min(-1)) to paraoxon against EEAChE. Analogs with Z = Br, I, or OTs were weak inhibitors of the AChEs, and methyl phosphonates (R = Me) were more potent than the corresponding ethyl phosphonates (R = Et). As expected, analogs with a thionate linkage (P=S) were poor inhibitors of the AChEs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.010
• 作为产物：
  描述：

  对硝基苯酚 在 三乙胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.33h， 生成 Ethylphosphonic acid 4-nitrophenyl ester
  参考文献：
  名称：

  Synthesis and anti-acetylcholinesterase properties of novel β- and γ-substituted alkoxy organophosphonates

  摘要：

  Activated organophosphate (OP) insecticides and chemical agents inhibit acetylcholinesterase (AChE) to form OP-AChE adducts. Whereas the structure of the OP correlates with the rate of inhibition, the structure of the OP-AChE adduct influences the rate at which post-inhibitory reactivation or aging phenomena occurs. In this report, we prepared a panel of beta-substituted ethoxy and gamma-substituted propoxy phosphonoesters of the type p-NO2PhO-P(X)(R)[(O(CH2)(n)Z] (R = Me, Et; X = O, S; n = 2, 3; Z = halogen, OTs) and examined the inhibition of three AChEs by select structures in the panel. The beta-fluoroethoxy methylphosphonate analog (R = Me, Z = F, n = 2) was the most potent anti-AChE compound comparable (k(i); similar to 6 x 10(6) M-1 min(-1)) to paraoxon against EEAChE. Analogs with Z = Br, I, or OTs were weak inhibitors of the AChEs, and methyl phosphonates (R = Me) were more potent than the corresponding ethyl phosphonates (R = Et). As expected, analogs with a thionate linkage (P=S) were poor inhibitors of the AChEs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.010

文献信息

• Balancing Specificity and Promiscuity in Enzyme Evolution: Multidimensional Activity Transitions in the Alkaline Phosphatase Superfamily
  作者：Bert van Loo、Christopher D. Bayer、Gerhard Fischer、Stefanie Jonas、Eugene Valkov、Mark F. Mohamed、Anastassia Vorobieva、Celine Dutruel、Marko Hyvönen、Florian Hollfelder

  DOI：10.1021/jacs.8b10290

  日期：2019.1.9

  adaptation by their capacity to promote multiple reactions. We employ a systematic comparative study of structure, sequence, and substrate specificity to track the evolution of specificity and reactivity between promiscuous members of clades of the alkaline phosphatase (AP) superfamily. Construction of a phylogenetic tree of protein sequences maps out the likely transition zone between arylsulfatases (ASs)

  高度熟练、混杂的酶可以成为功能进化的跳板，能够通过促进多重反应的能力避免在适应过程中丧失功能。我们采用结构、序列和底物特异性的系统比较研究来跟踪碱性磷酸酶 (AP) 超家族分支的混杂成员之间的特异性和反应性的演变。构建蛋白质序列的系统发育树，绘制出芳基硫酸酯酶 (AS) 和膦酸单酯水解酶 (PMH) 之间可能的过渡区。动力学分析表明，所有被表征的酶都具有四种不同的化学磷酸酯酶和磺酯酶活性，其初级反应的速率加速范围为 1011 至 1017 倍，混杂反应的速率加速范围为 109 至 1012 倍，表明催化性滥交在 AP 超家族中普遍存在。这种功能表征和晶体学揭示了一类新的 AS，它在序列上与已知的 PMH 非常相似，以至于没有被认为在功能上存在差异。基于对“过渡中”催化滥交快照的分析，我们开发了可能的模型，允许功能进化并确定多种活动之间的权衡方案。对于新的 AS，我们观察到很大程度上不变的底