3-(naphthoxymethyl)aniline

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphthoxymethyl)aniline
• 英文别名: 1-naphthyl 3-aminobenzyl ether；3-(Naphthalen-1-yloxymethyl)aniline
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: OPMLHBFHZXOITN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(naphthoxymethyl)aniline 在 potassium tert-butylate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-(3-((naphthalen-1-yloxy)methyl)phenyl)acetamide
  参考文献：
  名称：

  Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)- N -phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors

  摘要：

  Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl) thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42 nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of alpha-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.010
• 作为产物：
  描述：

  间硝基氯化苄 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 48.0h， 生成 3-(naphthoxymethyl)aniline
  参考文献：
  名称：

  三嗪-抗叶酸抑制利什曼原虫二氢叶酸还原酶与细胞生长的定量构效关系。

  摘要：

  已经建立了定量的构效关系，以抑制利什曼原虫主要的二氢叶酸还原酶（DHFR），并通过一系列的4,6-二氨基-1,2-二氢-2,2-二甲基-1来抑制前鞭毛体细胞的生长。 （3-取代的苯基）-s-三嗪s。DHFR的抑制作用与3-X取代基的疏水性修饰变量（pi'3），烷氧基指示剂变量（IOR），通过迭代获得的可抛弃参数（beta）和对空间进行参数化的变量密切相关方程中的效应（MR），log 1 / Ki = 0.65 pi'3-1.22 log（βX 10 pi'3 +1）-1.12IOR + 0.58MRY + 5.05（r = 0.965）。三嗪抑制培养中的主要细菌生长的EC50值与方程log 1 / EC50 = 0.21 pi 3 + 0.44 log 1 / Ki + 0.53（r = 0.960）相关。与人类的DHFR相比，其他脊椎动物与大肠杆菌L. major DHFR的不同之处在于

  DOI：

  10.1021/jm00390a017

文献信息

• Chemoselective hydrogenation of nitrobenzyl ethers to aminobenzyl ethers catalyzed by palladium–nickel bimetallic nanoparticles
  作者：Wenwen Chen、Hailin Bao、Dingsheng Wang、Xinyan Wang、Yadong Li、Yuefei Hu

  DOI：10.1016/j.tet.2015.10.037

  日期：2015.12

  A highly efficient and chemoselective hydrogenation of nitrobenzyl ethers to aminobenzyl ethers was developed by using a novel palladium nickel bimetallic nanocatalyst. Since the catalytic selectivity was resulted from the synergistic effects between two metals rather than the traditional catalyst poisons, the hydrogenation proceeded smoothly under additive-free conditions. Thus, the work-up procedure was as simple as to recover the catalyst by a magnetic separation and then to evaporate the solvent. (C) 2015 Elsevier Ltd. All rights reserved.
• Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)- N -phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors
  作者：Lingling Yang、Xiaobo Ma、Chen Yuan、Yanying He、Ling Li、Sha Fang、Wei Xia、Tao He、Shan Qian、Zhihong Xu、Guobo Li、Zhouyu Wang

  DOI：10.1016/j.ejmech.2017.04.010

  日期：2017.7

  Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl) thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42 nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of alpha-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Quantitative structure-activity relationship of triazine-antifolate inhibition of Leishmania dihydrofolate reductase and cell growth
  作者：Raymond G. Booth、Cynthia Dias Selassie、Corwin Hansch、Daniel V. Santi

  DOI：10.1021/jm00390a017

  日期：1987.7

  the electronic characteristics of the 3-X substituent of the parent triazine molecule. However, L. major DHFR is more sensitive to the steric effects and polarizability of the 3-X substituent. Our results indicate that triazines inhibit L. major promastigote growth via direct inhibition of DHFR as is shown by the good correlation between log 1/Ki values for inhibition of the purified enzyme and log

  已经建立了定量的构效关系，以抑制利什曼原虫主要的二氢叶酸还原酶（DHFR），并通过一系列的4,6-二氨基-1,2-二氢-2,2-二甲基-1来抑制前鞭毛体细胞的生长。 （3-取代的苯基）-s-三嗪s。DHFR的抑制作用与3-X取代基的疏水性修饰变量（pi'3），烷氧基指示剂变量（IOR），通过迭代获得的可抛弃参数（beta）和对空间进行参数化的变量密切相关方程中的效应（MR），log 1 / Ki = 0.65 pi'3-1.22 log（βX 10 pi'3 +1）-1.12IOR + 0.58MRY + 5.05（r = 0.965）。三嗪抑制培养中的主要细菌生长的EC50值与方程log 1 / EC50 = 0.21 pi 3 + 0.44 log 1 / Ki + 0.53（r = 0.960）相关。与人类的DHFR相比，其他脊椎动物与大肠杆菌L. major DHFR的不同之处在于