3-(2-(4-Ethylphenoxy)acetamido)-4-hydroxyphenylboronic acid | 1220716-03-9

• 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: 3-(2-(4-Ethylphenoxy)acetamido)-4-hydroxyphenylboronic acid
• 英文别名: [3-[[2-(4-ethylphenoxy)acetyl]amino]-4-hydroxyphenyl]boronic acid
• CAS: 1220716-03-9
• 化学式: C₁₆H₁₈BNO₅
• 分子量: 315.134
• InChiKey: BTRNPELDBAMPHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  23
• 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：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-ethylphenoxy)-N-(2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 3-(2-(4-Ethylphenoxy)acetamido)-4-hydroxyphenylboronic acid
  参考文献：
  名称：

  Boron-containing phenoxyacetanilide derivatives as hypoxia-inducible factor (HIF)-1α inhibitors

  摘要：

  A series of boron-containing phenoxyacetanilide derivatives 8a-f, 9a-f, 15, and 16 were synthesized as hypoxia-inducible factor (HIF)-1 alpha inhibitors. Among the compounds synthesized, carboranylphenoxy-acetanilide 16 (GN26361) was found to be a potent inhibitor against HIF-1 alpha accumulation under hypoxic conditions and inhibited the hypoxia-induced HIF-1 transcriptional activity in HeLa cells (IC50 = 0.74 mu M). Compound 16 suppressed hypoxia-induced HIF-1 alpha accumulation and vascular endothelial growth factor mRNA expression in a concentration-dependent manner without affecting the expression of HIF-1 alpha mRNA. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.037

文献信息

• Boron-containing phenoxyacetanilide derivatives as hypoxia-inducible factor (HIF)-1α inhibitors
  作者：Kazuki Shimizu、Minako Maruyama、Yuka Yasui、Hidemitsu Minegishi、Hyun Seung Ban、Hiroyuki Nakamura

  DOI：10.1016/j.bmcl.2009.12.037

  日期：2010.2

  A series of boron-containing phenoxyacetanilide derivatives 8a-f, 9a-f, 15, and 16 were synthesized as hypoxia-inducible factor (HIF)-1 alpha inhibitors. Among the compounds synthesized, carboranylphenoxy-acetanilide 16 (GN26361) was found to be a potent inhibitor against HIF-1 alpha accumulation under hypoxic conditions and inhibited the hypoxia-induced HIF-1 transcriptional activity in HeLa cells (IC50 = 0.74 mu M). Compound 16 suppressed hypoxia-induced HIF-1 alpha accumulation and vascular endothelial growth factor mRNA expression in a concentration-dependent manner without affecting the expression of HIF-1 alpha mRNA. (C) 2009 Elsevier Ltd. All rights reserved.