1-(4-((3-nitrobenzyl)oxy)phenyl)ethanone | 103981-34-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-((3-nitrobenzyl)oxy)phenyl)ethanone
• 英文别名: 1-[4-[(3-Nitrophenyl)methoxy]phenyl]ethanone
• CAS: 103981-34-6
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: COWPVELYFBSBNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-((3-nitrobenzyl)oxy)phenyl)ethanone 在 盐酸 、 铁粉 作用下， 以 乙醇 为溶剂， 反应 17.0h， 生成 Methyl 3-[3-[(4-acetylphenoxy)methyl]anilino]-3-oxopropanoate
  参考文献：
  名称：

  Synthesis and antiallergic activity of a novel series of 5-lipoxygenase inhibitors

  摘要：

  A series of novel substituted [[(phenoxymethyl)phenyl]amino]oxoalkanoic acid esters have been synthesized. These compounds were tested in vitro for their ability to inhibit the synthesis of 5-hydroxyeicosatetraenoic acid and leukotriene (LT) B4 from rat polymorphonuclear leukocytes (PMN) and in vivo as inhibitors ovalbumin- (OA) and LTD4-induced bronchospasm in the guinea pig. Compounds 5-12 and 25 had IC50's between 1 and 5.6 microM in the rat PMN 5-lipoxygenase assay. Compounds 1, 3, and 16 inhibited OA-induced bronchoconstriction (61%, 64%, and 57%, respectively), but only 1 showed activity against LTD4-induced bronchoconstriction. When tested against LTD4-induced contraction of isolated guinea pig tracheal spiral strips, 1 was a competitive inhibitor with a pKB of 4.94.

  DOI：

  10.1021/jm00161a031
• 作为产物：
  描述：

  3-硝基溴苄 、 对羟基苯乙酮 在 potassium carbonate 、 caesium carbonate 作用下， 生成 1-(4-((3-nitrobenzyl)oxy)phenyl)ethanone
  参考文献：
  名称：

  Synthesis and antiallergic activity of a novel series of 5-lipoxygenase inhibitors

  摘要：

  A series of novel substituted [[(phenoxymethyl)phenyl]amino]oxoalkanoic acid esters have been synthesized. These compounds were tested in vitro for their ability to inhibit the synthesis of 5-hydroxyeicosatetraenoic acid and leukotriene (LT) B4 from rat polymorphonuclear leukocytes (PMN) and in vivo as inhibitors ovalbumin- (OA) and LTD4-induced bronchospasm in the guinea pig. Compounds 5-12 and 25 had IC50's between 1 and 5.6 microM in the rat PMN 5-lipoxygenase assay. Compounds 1, 3, and 16 inhibited OA-induced bronchoconstriction (61%, 64%, and 57%, respectively), but only 1 showed activity against LTD4-induced bronchoconstriction. When tested against LTD4-induced contraction of isolated guinea pig tracheal spiral strips, 1 was a competitive inhibitor with a pKB of 4.94.

  DOI：

  10.1021/jm00161a031

文献信息

• Acetophenone derivatives: novel and potent small molecule inhibitors of monoamine oxidase B
  作者：Zhi-Min Wang、Xue-Mei Li、Wei Xu、Fan Li、Jin Wang、Ling-Yi Kong、Xiao-Bing Wang

  DOI：10.1039/c5md00357a

  日期：——

  series of acetophenone derivatives have been designed, synthesized and evaluated for human monoamine oxidase A and B inhibitory activity in vitro. Most of the tested compounds acted preferentially on MAO-B with IC50 values in the nanomolar range and weak or no inhibition of MAO-A. In particular, compounds 1j (IC50 = 12.9 nM) and 2e (IC50 = 11.7 nM) were the most potent MAO-B inhibitors being 2.76- and 2

  已经设计，合成和评估了两个系列的苯乙酮衍生物在体外对人单胺氧化酶A和B的抑制活性。大多数测试的化合物优先以30纳摩尔范围的IC 50值对MAO-B起作用，对MAO-A的抑制作用弱或无抑制作用。特别是化合物1j（IC 50 = 12.9 nM）和2e（IC 50= 11.7 nM）是最有效的MAO-B抑制剂，其活性比司来吉兰高2.76倍和2.99倍。此外，MAO-B抑制的结构-活性关系表明，苯乙酮部分C3和C4处的取代基，特别是被卤素取代的苄氧基取代，对MAO-B抑制更有利。已经进行了分子对接和动力学研究以解释MAO-B与苯乙酮衍生物的结合模式。此外，代表性化合物1j和2e在SH-SY5Y细胞中显示出低神经毒性。可以得出结论，苯乙酮衍生物可用于开发有望用于治疗神经退行性疾病的先导化合物。
• 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.
• Synthesis and antiallergic activity of a novel series of 5-lipoxygenase inhibitors
  作者：Kenneth L. Kees、John H. Musser、Joseph Chang、Maureen Skowronek、Alan J. Lewis

  DOI：10.1021/jm00161a031

  日期：1986.11

  A series of novel substituted [[(phenoxymethyl)phenyl]amino]oxoalkanoic acid esters have been synthesized. These compounds were tested in vitro for their ability to inhibit the synthesis of 5-hydroxyeicosatetraenoic acid and leukotriene (LT) B4 from rat polymorphonuclear leukocytes (PMN) and in vivo as inhibitors ovalbumin- (OA) and LTD4-induced bronchospasm in the guinea pig. Compounds 5-12 and 25 had IC50's between 1 and 5.6 microM in the rat PMN 5-lipoxygenase assay. Compounds 1, 3, and 16 inhibited OA-induced bronchoconstriction (61%, 64%, and 57%, respectively), but only 1 showed activity against LTD4-induced bronchoconstriction. When tested against LTD4-induced contraction of isolated guinea pig tracheal spiral strips, 1 was a competitive inhibitor with a pKB of 4.94.