4-(4-(benzyloxy)phenoxy)aniline | 155828-47-0

• 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: 4-(4-(benzyloxy)phenoxy)aniline
• 英文别名: 4-[4-(Benzyloxy)phenoxy]aniline；4-(4-phenylmethoxyphenoxy)aniline
• CAS: 155828-47-0
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: VDLNUBYKPOOEAF-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  463.9±35.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-(benzyloxy)phenoxy)aniline 在 甲酸 、 4 A molecular sieve 、 溴 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of nonpeptide mimetics of ω-conotoxin GVIA

  摘要：

  A benzothiazole-derived compound (4a) designed to mimic the C-alpha-C-beta bond vectors and terminal functionalities of Lys2, TyrI3 and Arg17 in omega-conotoxin GVIA was synthesised, together with analogues (4b-d), which had each side-chain mimic systematically truncated or eliminated. The affinity of these compounds for rat brain N-type and P/Q-type voltage gated calcium channels (VGCCs) was determined. In terms of N-type channel affinity and selectivity, two of these compounds (4a and 4d) were found to be highly promising, first generation mimetics of omega-conotoxin. The fully functionalised mimetic (4a) showed low PM binding affinity to N-type VGCCs (IC50 = 1.9 muM) and greater than 20-fold selectivity for this channel sub-type over P/Q-type VGCCs, whereas the mimetic in which the guanidine-type side chain was truncated back to an amine (4d, IC50 = 4.1 muM) showed a greater than 25-fold selectivity for the N-type channel. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.040
• 作为产物：
  描述：

  对二硝基苯 在 sodium dithionite 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 4-(4-(benzyloxy)phenoxy)aniline
  参考文献：
  名称：

  Synthesis and biological evaluation of nonpeptide mimetics of ω-conotoxin GVIA

  摘要：

  A benzothiazole-derived compound (4a) designed to mimic the C-alpha-C-beta bond vectors and terminal functionalities of Lys2, TyrI3 and Arg17 in omega-conotoxin GVIA was synthesised, together with analogues (4b-d), which had each side-chain mimic systematically truncated or eliminated. The affinity of these compounds for rat brain N-type and P/Q-type voltage gated calcium channels (VGCCs) was determined. In terms of N-type channel affinity and selectivity, two of these compounds (4a and 4d) were found to be highly promising, first generation mimetics of omega-conotoxin. The fully functionalised mimetic (4a) showed low PM binding affinity to N-type VGCCs (IC50 = 1.9 muM) and greater than 20-fold selectivity for this channel sub-type over P/Q-type VGCCs, whereas the mimetic in which the guanidine-type side chain was truncated back to an amine (4d, IC50 = 4.1 muM) showed a greater than 25-fold selectivity for the N-type channel. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.040

文献信息

• Discovery of 1,2,4-triazole-1,3-disulfonamides as dual inhibitors of mitochondrial complex II and complex III
  作者：Hua Cheng、Yan-Qing Shen、Xia-Yan Pan、Yi-Ping Hou、Qiong-You Wu、Guang-Fu Yang

  DOI：10.1039/c5nj00215j

  日期：——

  1,2,4-Triazole-1,3-disulfonamide derivatives as dual function inhibitors of mitochondrial complex II (SQR) and complex III (cytbc₁) were discovered.

  1,2,4-三唑-1,3-二磺酰胺衍生物被发现具有线粒体复合物II（SQR）和复合物III（细胞色素bc1）的双功能抑制剂作用。
• Potentiators of glutamate receptors
  申请人：——

  公开号：US20040006114A1

  公开（公告）日：2004-01-08

  The present invention relates to potentiators of metabotropic glutamate receptor function and specifically provides compounds of formula I, compositions thereof and methods of using the same. 1

  本发明涉及代谢型谷氨酸受体功能的增强剂，具体提供了化合物I的公式、其组合物以及使用方法。
• Synthesis, biochemical evaluation and computational simulations of new cytochrome bc1 complex inhibitors based on N-(4-aryloxyphenyl) phthalimides
  作者：Hua Cheng、Yan Fu、Qing Chang、Ni Zhang、Mengwei Bu、Yan Niu、Qiongyou Wu、Cheng Chen、Francis Verpoort

  DOI：10.1016/j.cclet.2018.10.008

  日期：2018.12

  or complex III) is an attractive target for the discovery of numerous pharmaceuticals and pesticides. In order to identify new lead structures for this target, a new series of molecules, N-(4-aryloxyphenyl)phthalimides, were designed and synthesized in a straightforward manner. Our design strategy was to introduce a 4-aryloxyphenyl group, a fragment which exhibited promising bc1 complex-inhibiting

  摘要细胞色素bc1复合物（bc1复合物或复合物III）是发现众多药物和农药的诱人靶标。为了确定用于该靶标的新的铅结构，以简单的方式设计并合成了一系列新的分子N-（4-芳氧基苯基）邻苯二甲酰亚胺。我们的设计策略是将有价值的N-芳基邻苯二甲酰亚胺骨架的芳基引入一个4-芳基氧基苯基基团，该片段表现出有希望的bc1络合物抑制特性。之后，对新合成的化合物进行了生化评估，结果表明几种化合物对琥珀酸-细胞色素还原酶（SCR，线粒体复合物II和bc1复合物的混合物）具有良好的活性。进一步的研究证实3e'，本文中的一种代表性化合物被鉴定为bc1复合物的抑制剂。此外，还进行了计算模拟以更好地理解3e'与酶复合物的结合，这表明3e'应与bc1复合物的Qo位点结合。因此，我们认为本文可以为其他bc1复杂抑制剂的合成和发现提供坚实的平台。
• Design, Synthesis and Antitumor Activity of Novel Cis-Furoquinoline Derivatives
  作者：Jie Li、Shuchen Pei、Yingxi Zhu、Jianbo Wu、Yin Chen、Weiyu Zhang、Yong Wu

  DOI：10.2174/157018012799859909

  日期：2012.4.26

  A series of novel cis-furoquinoline derivatives was synthesized and tested for their antitumor activities in vitro against HepG2 cells, Lu-04 cells and Leu02 cells to evaluate structure-activity relationships. Assay-based antiproliferative activity study revealed that several compounds had significant effects on cytotoxicity, among which compounds 2f, 2l, 2q were found to be the most active compounds. Above all, compounds 2f, 2l, 2q would be potential anticancer agents which deserved further research.

  合成了一系列新型顺式呋喃喹啉衍生物，并在体外测试了它们对 HepG2 细胞、Lu-04 细胞和 Leu02 细胞的抗肿瘤活性，以评估其结构-活性关系。基于测定法的抗增殖活性研究发现，几个化合物对细胞毒性有显著影响，其中化合物 2f、2l 和 2q 的活性最高。总之，化合物 2f、2l 和 2q 将成为潜在的抗癌药物，值得进一步研究。
• ω-Conotoxin GVIA mimetics based on an anthranilamide core: Effect of variation in ammonium side chain lengths and incorporation of fluorine
  作者：Asa Andersson、Jonathan B. Baell、Peter J. Duggan、Janease E. Graham、Richard J. Lewis、Natalie G. Lumsden、C. Elisabet Tranberg、Kellie L. Tuck、Aijun Yang

  DOI：10.1016/j.bmc.2009.07.063

  日期：2009.9

  A number of omega-conotoxin GVIA mimetics based on an anthranilamide core were prepared and tested for their affinity for rat brain Ca(v)2.2 channels. Features such as the presence of hydroxyl and fluoro substituents on the tyrosine side chain mimic, the length of the chains on the lysine/arginine side chain mimics and the use of diguanidino and diamino substituents rather than mono-guanidine/mono-amine substitution were examined. The diguanidinylated compounds proved to be the most active and deletion of the hydroxyl substituent had a limited influence on activity. The SAR associated with variation in the lysine/arginine side chain mimics was not strong. The introduction of a fluoro substituent into the tyrosine mimic produced the most active compound prepared in this study (2g), with an EC50 at rat brain Ca(v)2.2 channels of 6 mu M. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.