N-(3-benzoylphenyl)-2-(4-ethynylphenoxy)acetamide | 1242177-77-0

• 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: N-(3-benzoylphenyl)-2-(4-ethynylphenoxy)acetamide
• CAS: 1242177-77-0
• 化学式: C₂₃H₁₇NO₃
• 分子量: 355.393
• InChiKey: KHRUIAYWTNWJGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  癸硼烷 、 N-(3-benzoylphenyl)-2-(4-ethynylphenoxy)acetamide 以 甲苯 、 乙腈 为溶剂， 反应 48.0h， 生成
  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
• 作为产物：
  描述：

  对溴苯氧乙酸 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 N-(3-benzoylphenyl)-2-(4-ethynylphenoxy)acetamide
  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

• Identification of HSP60 as a Primary Target of <i>o</i>-Carboranylphenoxyacetanilide, an HIF-1α Inhibitor
  作者：Hyun Seung Ban、Kazuki Shimizu、Hidemitsu Minegishi、Hiroyuki Nakamura

  DOI：10.1021/ja104739t

  日期：2010.9.1

  We succeeded in the design and synthesis of multifunctional chemical probes of the HIF-1 alpha inhibitor carboranylphenoxyacetanilide (1) that combine photoaffinity labeling and click reaction to identify the target protein. HSP60 was identified as a primary target protein of 1 using the chemical probes 2 and 3. Furthermore, HSP60 inhibitor 4 suppressed hypoxia-induced HIF activation, indicating that HSP60 affects HIF-1 alpha accumulation directly or indirectly.