2-bromo-N-[2-phenylmethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide | 1418738-50-7

• 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: 2-bromo-N-[2-phenylmethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide
• CAS: 1418738-50-7
• 化学式: C₂₁H₂₅BBrNO₄
• 分子量: 446.149
• InChiKey: WPNYFIOWLFUIAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxyphenyl)-1,7-dicarba-closo-dodecaborane 、 2-bromo-N-[2-phenylmethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of meta-carborane-containing phenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity

  摘要：

  meta-Carboranylphenoxyacetanilides were synthesized by copper catalyzed coupling reaction of meta-carborane and phenyl iodides. The synthesized compounds were evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, meta-carborane containing phenoxyanilides 2d and 2h, which have an isobutyl group on meta-carborane, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity toward HeLa cell-based reporter gene assay with the IC50 values of 0.73 and 0.55 mu M, respectively. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.05.029
• 作为产物：
  描述：

  1-苄氧基-4-溴-2-硝基苯 在 吡啶 、 4-二甲氨基吡啶 、 1,1'-双(二苯基膦)二茂铁 、 potassium acetate 、 铁粉 、 氯化铵 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2-bromo-N-[2-phenylmethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of meta-carborane-containing phenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity

  摘要：

  meta-Carboranylphenoxyacetanilides were synthesized by copper catalyzed coupling reaction of meta-carborane and phenyl iodides. The synthesized compounds were evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, meta-carborane containing phenoxyanilides 2d and 2h, which have an isobutyl group on meta-carborane, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity toward HeLa cell-based reporter gene assay with the IC50 values of 0.73 and 0.55 mu M, respectively. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.05.029

文献信息

• Development of hypoxia-inducible factor (HIF)-1α inhibitors: Effect of ortho-carborane substituents on HIF transcriptional activity under hypoxia
  作者：Hiroyuki Nakamura、Yuka Yasui、Minako Maruyama、Hidemitsu Minegishi、Hyun Seung Ban、Shinichi Sato

  DOI：10.1016/j.bmcl.2012.11.081

  日期：2013.2

  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.
• ortho-Carboranylphenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity and heat shock protein (HSP) 60 chaperon activity
  作者：Guangzhe Li、Soyoko Azuma、Shinichi Sato、Hidemitsu Minegishi、Hiroyuki Nakamura

  DOI：10.1016/j.bmcl.2015.04.088

  日期：2015.7

  ortho-Carboranylphenoxy derivatives were synthesized and evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, compound 1d showed the most significant inhibition of hypoxia-induced HIF-1 transcriptional activity with the IC50 of 0.53 mu M. Furthermore, compound 1h was found to possess the most significant inhibition of heat shock protein (HSP) 60 chaperon activity among the reported inhibitors: the IC50 toward the porcine heart malate dehydrogenase (MDH) refolding assay was 0.35 mu M. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of meta-carborane-containing phenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity
  作者：Guangzhe Li、Soyoko Azuma、Hidemitsu Minegishi、Hiroyuki Nakamura

  DOI：10.1016/j.jorganchem.2015.05.029

  日期：2015.12

  meta-Carboranylphenoxyacetanilides were synthesized by copper catalyzed coupling reaction of meta-carborane and phenyl iodides. The synthesized compounds were evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, meta-carborane containing phenoxyanilides 2d and 2h, which have an isobutyl group on meta-carborane, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity toward HeLa cell-based reporter gene assay with the IC50 values of 0.73 and 0.55 mu M, respectively. (C) 2015 Elsevier B.V. All rights reserved.