N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-chloroaniline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-chloroaniline
• 英文别名: N-(1,3-benzodioxol-5-ylmethyl)-4-chloroaniline
• 化学式: C₁₄H₁₂ClNO₂
• mdl: MFCD00441532
• 分子量: 261.708
• InChiKey: QNSGPBQRNKLKKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  胡椒醛 、 对氯苯胺 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以71%的产率得到N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-chloroaniline
  参考文献：
  名称：

  Synthesis and evaluation of N-analogs of 1,2-diarylethane as Helicobacter pylori urease inhibitors

  摘要：

  Therapies based on urease inhibition are now seriously considered as the first line of treatment for infections caused by Helicobacter pylori. However, the present inhibitors are ineffective or unstable in highly acidic gastric juice. Here, we report a series of benzylanilines as effective inhibitors of H. pylori urease. Out of the obtained twenty-one compounds, N-(3,4-dihydroxybenzyl)-4-nitroaniline (4) was evaluated in detail and shows promising features for development as anti-H. pylori agent. Excellent potency against urease in both cell-free extract and intact cell was observed at low concentrations of 4 (IC50 = 0.62 +/- 0.04 and 1.92 +/- 0.09 mu M), which showed over 29- and 54-fold increase in potency with respect to the positive control AHA. The SAR analysis revealed that protection of 3,4-dihydroxy group of 4 as methoxy or changes of 4-NO2 will result in a moderate to dramatic decrease in potency. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.014

文献信息

• Diaryl compounds and pharmaceutical formulations containing them
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0028305A1

  公开（公告）日：1981-05-13

  Known and novel compounds of formula (I) wherein Ar are the same or different and each is a substituted or unsubstituted phenyl group and Z is a bond, sulphur, -CHOH, or -C=O; and X is oxygen, sulphur, -CH2 or -NH- when Y is -CH2; or X is -CH2 when Y is oxygen; or X - Y together is -CH=CH, are active against viruses, especially rhinoviruses. Methods for producing the compounds are described, as are pharmaceutical formulations and methods for administering the compounds to cure or prevent rhinoviral infections.

  已知和新型的式(I)化合物 其中 Ar 相同或不同，且各为取代或未取代的苯基，以及 Z 是键、硫、-CHOH 或 -C=O；以及 当 Y 为-CH2 时，X 为氧、硫、-CH2 或-NH-；或 当 Y 是氧时，X 是-CH2；或 X-Y合起来是-CH=CH，对病毒，特别是鼻病毒有活性。本文介绍了生产这些化合物的方法，以及使用这些化合物治疗或预防鼻病毒感染的药物制剂和方法。
• In(OTf)3 catalyzed N-benzylation of amines utilizing benzyl alcohols in water
  作者：Jin-Ming Yang、Ran Jiang、Lin Wu、Xiao-Ping Xu、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tet.2013.07.010

  日期：2013.9

  An In(OTf)(3)-catalyzed N-benzylation of amines utilizing benzyl alcohols through direct C-O bond activation has been reported. The reaction was performed in water without any base, additive, ligand or inert gas protection to afford the chem-selective mono- or bis-alkylated aromatic amines in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Ethynyl Ketene-<i>S</i>,<i>S</i>-acetals:  The Highly Reactive Electron-Rich Dienophiles and Applications in the Synthesis of 4-Functionalized Quinolines via a One-Pot Three-Component Reaction
  作者：Yu-Long Zhao、Wei Zhang、Shuang Wang、Qun Liu

  DOI：10.1021/jo070069q

  日期：2007.6.1

  An efficient synthetic method for 4-functionalized quinoline derivatives, 4-((1,3-dithian-2-ylidene)methyl)quinolines, has been developed. Mediated by trifluoromethanesulfonic acid, ethynyl ketene-S,S-acetals can react in a one-pot procedure with various arylamines and aldehydes under mild conditions to give the corresponding quinoline derivatives in good to high yields via a consecutive arylimine formation, regiospecific aza-Diels-Alder (Povarov) reaction, and reductive amination.
• Synthesis and evaluation of N-analogs of 1,2-diarylethane as Helicobacter pylori urease inhibitors
  作者：Zhu-Ping Xiao、Wei-Kang Shi、Peng-Fei Wang、Wei Wei、Xiao-Tong Zeng、Ji-Rong Zhang、Na Zhu、Miao Peng、Bin Peng、Xiao-Yi Lin、Hui Ouyang、Xiao-Chun Peng、Guang-Cheng Wang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2015.06.014

  日期：2015.8

  Therapies based on urease inhibition are now seriously considered as the first line of treatment for infections caused by Helicobacter pylori. However, the present inhibitors are ineffective or unstable in highly acidic gastric juice. Here, we report a series of benzylanilines as effective inhibitors of H. pylori urease. Out of the obtained twenty-one compounds, N-(3,4-dihydroxybenzyl)-4-nitroaniline (4) was evaluated in detail and shows promising features for development as anti-H. pylori agent. Excellent potency against urease in both cell-free extract and intact cell was observed at low concentrations of 4 (IC50 = 0.62 +/- 0.04 and 1.92 +/- 0.09 mu M), which showed over 29- and 54-fold increase in potency with respect to the positive control AHA. The SAR analysis revealed that protection of 3,4-dihydroxy group of 4 as methoxy or changes of 4-NO2 will result in a moderate to dramatic decrease in potency. (C) 2015 Elsevier Ltd. All rights reserved.