2-(2-nitrophenoxy)-1-mesyloxyethane | 850895-60-2

• 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: 2-(2-nitrophenoxy)-1-mesyloxyethane
• 英文别名: 2-(2-Nitrophenoxy)ethyl methanesulfonate；2-(2-nitrophenoxy)ethyl methanesulfonate
• CAS: 850895-60-2
• 化学式: C₉H₁₁NO₆S
• 分子量: 261.255
• InChiKey: MHPUQDVNMZFYEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-nitrophenoxy)-1-mesyloxyethane 在 10% Pd/C 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[2-(二甲基氨基)乙氧基]苯胺
  参考文献：
  名称：

  Pyrrolidinyl phenylurea derivatives as novel CCR3 antagonists

  摘要：

  Optimization starting with our lead compound 1 (IC50 = 4.9 nM) led to the identification of pyrrolidinyl phenylurea derivatives. Further modification toward improvement of the bioavailability provided (R)-1-(1-((6-fluoronaphthalen-2-yl)methyl)pyrrolidin-3-yl)-3-(2-(2-hydroxyethoxy)phenyl)urea 32 (IC50 = 1.7 nM), a potent and orally active CCR3 antagonist. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.035
• 作为产物：
  描述：

  1-氟-2-硝基苯 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(2-nitrophenoxy)-1-mesyloxyethane
  参考文献：
  名称：

  Pyrrolidinyl phenylurea derivatives as novel CCR3 antagonists

  摘要：

  Optimization starting with our lead compound 1 (IC50 = 4.9 nM) led to the identification of pyrrolidinyl phenylurea derivatives. Further modification toward improvement of the bioavailability provided (R)-1-(1-((6-fluoronaphthalen-2-yl)methyl)pyrrolidin-3-yl)-3-(2-(2-hydroxyethoxy)phenyl)urea 32 (IC50 = 1.7 nM), a potent and orally active CCR3 antagonist. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.035

文献信息

• The replacement of the 2-methoxy substituent of N-((6,6-diphenyl-1,4-dioxan-2-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-amine improves the selectivity for 5-HT1A receptor over α1-adrenoceptor and D2-like receptor subtypes
  作者：Fabio Del Bello、Alessandro Bonifazi、Mario Giannella、Gianfabio Giorgioni、Alessandro Piergentili、Riccardo Petrelli、Carlo Cifani、Maria Vittoria Micioni Di Bonaventura、Thomas M. Keck、Angelica Mazzolari、Giulio Vistoli、Antonio Cilia、Elena Poggesi、Rosanna Matucci、Wilma Quaglia

  DOI：10.1016/j.ejmech.2016.09.026

  日期：2017.1

  interactions of the reported ligands, docking studies, using 5-HT1A and α1d-AR models generated by homology techniques, and a retrospective computational study were performed. The results highlighted that proper substituents in position 2 of the phenoxy moiety of 3 selectively address the ligands toward 5-HT1A receptor with respect to α1-ARs and D2-like receptor subtypes. Methoxymethylenoxy derivative

  ñ - （（6,6-二苯基-1,4-二恶烷-2-基）甲基）-2-（2-甲氧基苯氧基）乙烷-1-胺（3）是一种有效的5-HT 1A受体和α 1D -肾上腺素能受体（α1d -AR）配体。类似物5-10被合理地设计和制备，以评估是否在取代基中的电子和/或亲脂性的邻位其苯氧基部分的上施加的亲和/活性的任何有利的作用位置在5-HT 1A受体和改进对α选择性1 - AR。为了使实验观察合理化并获得有关已报道配体的受体-配体相互作用的信息，需要使用5-HT 1A和α进行对接研究通过同源技术生成1d -AR模型，并进行回顾性计算研究。结果强调了的苯氧基部分的2位上，适当的取代基3选择性地寻址朝向5-HT的配位体1A受体相对于α 1个-ARs和d 2 -样受体亚型。甲氧基甲基烯氧基衍生物9表现出最佳的5-HT 1A选择性和对5-HT 1A受体的最高效能，表现为部分激动剂。最后9在小鼠的明/暗探索测试中进行
• QSAR study for a novel series of ortho monosubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101
  作者：Laura Fumagalli、Cristiano Bolchi、Simona Colleoni、Marco Gobbi、Barbara Moroni、Marco Pallavicini、Alessandro Pedretti、Luigi Villa、Giulio Vistoli、Ermanno Valoti

  DOI：10.1016/j.bmc.2005.01.034

  日期：2005.4

  A number of (S)- and (R)-2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes unsubstituted or ortho monosubstituted at the phenoxy moiety were synthesized and tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR alpha(1d)-AR and the 5-HT1A receptor. The affinity values of the new compounds 1-16 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha(1) antagonist WB4101, finding that the unsubstituted derivative (S)-1 and the o-methyl, the o-t-butyl, the o-fluoro and the o-methoxy derivatives, (S)-2, (S)-4, (S)-8 and (S)-16, respectively, display a significantly specific 5-HT1A affinity, very close, with the exception of (S)-4, to the almost nanomolar one of (S)-WB4101. Otherwise sensible affinity decreases were recorded for the three alpha(1)-AR subtypes. A classical quantitative structure-activity relationship (Hansch) analysis was successfully applied to compounds (S)-1 to (S)-16 and (S)-WB4101 to rationalize such binding data. (c) 2005 Elsevier Ltd. All rights reserved.
• Pyrrolidinyl phenylurea derivatives as novel CCR3 antagonists
  作者：Aiko Nitta、Yosuke Iura、Hideki Inoue、Ippei Sato、Koichiro Morihira、Hirokazu Kubota、Tatsuaki Morokata、Makoto Takeuchi、Mitsuaki Ohta、Shin-ichi Tsukamoto、Takayuki Imaoka、Toshiya Takahashi

  DOI：10.1016/j.bmcl.2012.09.035

  日期：2012.11

  Optimization starting with our lead compound 1 (IC50 = 4.9 nM) led to the identification of pyrrolidinyl phenylurea derivatives. Further modification toward improvement of the bioavailability provided (R)-1-(1-((6-fluoronaphthalen-2-yl)methyl)pyrrolidin-3-yl)-3-(2-(2-hydroxyethoxy)phenyl)urea 32 (IC50 = 1.7 nM), a potent and orally active CCR3 antagonist. (C) 2012 Elsevier Ltd. All rights reserved.