ethyl 3-amino-4-(benzyloxy) benzoate | 1215948-43-8

• 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: ethyl 3-amino-4-(benzyloxy) benzoate
• 英文别名: Ethyl 3-amino-4-(benzyloxy)benzoate；ethyl 3-amino-4-phenylmethoxybenzoate
• CAS: 1215948-43-8
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: WVKKQXQOZRDCBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-4-(benzyloxy) benzoate 在 tetrafluoroboric acid 、 palladium diacetate 、 potassium carbonate 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 生成 ethyl 6H-benzo[c]chromene-2-carboxylate
  参考文献：
  名称：

  Synthesis of substituted 6H-benzo[c]chromenes: a palladium promoted ring closure of diazonium tetrafluoroborates

  摘要：

  A highly efficient palladium-catalysed phenyl diazonium tetrafluoroborate participation of C-H activation ring closure protocol has been developed. A series of 6H-benzo[c]chromenes have been synthesized by intramolecular cyclization of ortho diazonium salts tetrafluoroborate of benzyloxyphenyl (Method A), or phenoxymethyl phenyl (Method B). The transformation allows the synthesis of 6H-benzo[c]chromenes with a wide variety of functional groups and substitution patterns from simple and easily accessible precursors. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.038
• 作为产物：
  描述：

  4-羟基-3-硝基苯甲酸 在 硫酸 、 铁粉 、 potassium carbonate 、 氯化铵 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 13.0h， 生成 ethyl 3-amino-4-(benzyloxy) benzoate
  参考文献：
  名称：

  Development of hypoxia-inducible factor (HIF)-1α inhibitors: Effect of ortho-carborane substituents on HIF transcriptional activity under hypoxia

  摘要：

  A series of substituted ortho-carboranylphenoxyacetanilides were synthesized and evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter assay in HeLa cells expressing the HRE-dependent firefly luciferase reporter construct (HRE-Luc) and constitutively expressing CMV-driven Renilla luciferase reporter, and their ability to inhibit cell growth (GI(50)) using the MTT assay. Among the compounds synthesized, 1g and 1l showed significant inhibition of hypoxia-induced HIF-1 transcriptional activity (IC50: 1.9 +/- 0.4 and 1.4 +/- 0.2 mu M, respectively). Both compounds suppressed HIF-1 alpha accumulation in a concentration-dependent manner. The porcine heart malate dehydrogenase (MDH) refolding assay revealed that compound 1l inhibited human Hsp60 chaperone activity (IC50: 6.80 +/- 0.25 mu M) and this inhibition activity was higher than that of ETB (IC50: 10.9 +/- 0.63 mu M). (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.081

文献信息

• Syntheses and characterization of nimesulide derivatives for dual enzyme inhibitors of both cyclooxygenase-1/2 and 5-lipoxygenase
  作者：Yue Li、Shu-Han Chen、Tian-Miao Ou、Jia-Heng Tan、Ding Li、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.bmc.2011.01.043

  日期：2011.3

  Cyclooxygenase-1/2 (COX-1/2) and 5-lipoxygenase (5-LOX) are enzymes in two different pathways in the inflammatory process. In the present study, a variety of new nimesulide derivatives were synthesized through incorporation of a 5-LOX pharmacophore into nimesulide followed with some structural modifications, which were then characterized for dual enzyme inhibitors for these two types of enzymes. Their structure-activity relationships (SARs) were studied, and compound 20f was found to be an excellent dual enzyme inhibitor. Its binding conformation and interaction mode were studied with molecular docking experiments. Compound 20f could become a lead compound for further development for potential anti-inflammatory drugs. (C) 2011 Elsevier Ltd. All rights reserved.