4-(6-(cyclohexylmethoxy)hexyl)aniline | 1266666-02-7

• 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: 4-(6-(cyclohexylmethoxy)hexyl)aniline
• 英文别名: 4-[6-(cyclohexylmethoxy)hexyl]aniline
• CAS: 1266666-02-7
• 化学式: C₁₉H₃₁NO
• 分子量: 289.461
• InChiKey: PIRRXCWGGOLQQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(6-(cyclohexylmethoxy)hexyl)aniline 、 1-氰基-1-环丙烷羧酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 VPC143113
  参考文献：
  名称：

  Development of Amidine-Based Sphingosine Kinase 1 Nanomolar Inhibitors and Reduction of Sphingosine 1-Phosphate in Human Leukemia Cells

  摘要：

  Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.

  DOI：

  10.1021/jm2001053
• 作为产物：
  描述：

  环己甲醇 在 sodium hydride 、 溶剂黄146 、 9-硼双环[3.3.1]壬烷 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 48.75h， 生成 4-(6-(cyclohexylmethoxy)hexyl)aniline
  参考文献：
  名称：

  Development of Amidine-Based Sphingosine Kinase 1 Nanomolar Inhibitors and Reduction of Sphingosine 1-Phosphate in Human Leukemia Cells

  摘要：

  Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.

  DOI：

  10.1021/jm2001053

文献信息

• IMIDAMIDE SPHINGOSINE KINASE INHIBITORS
  申请人：Lynch Kevin R.

  公开号：US20120214858A1

  公开（公告）日：2012-08-23

  Imidamide (amidine) analogs that can inhibit the activity of sphingosine kinase 1 and sphingosine kinase 2 (SphK1 & SphK2) are provided. The compounds can prevent angiogenesis in tumors.

  提供可以抑制神经酰胺激酶1和神经酰胺激酶2（SphK1和SphK2）活性的Imidamide（胺基）类似物。这些化合物可以预防肿瘤中的血管生成。
• Imidamide sphingosine kinase inhibitors
  申请人：Lynch Kevin R.

  公开号：US09421177B2

  公开（公告）日：2016-08-23

  Imidamide (amidine) analogs that can inhibit the activity of sphingosine kinase 1 and sphingosine kinase 2 (SphK1 & SphK2) are provided. The compounds can prevent angiogenesis in tumors.

  提供了能够抑制鞘氨醇激酶1和鞘氨醇激酶2(SphK1 & SphK2)活性的imidamide（酰胺）类似物。这些化合物可以防止肿瘤的血管生成。
• US9421177B2
  申请人：——

  公开号：US9421177B2

  公开（公告）日：2016-08-23
• US9908849B2
  申请人：——

  公开号：US9908849B2

  公开（公告）日：2018-03-06
• [EN] IMIDAMIDE SPHINGOSINE KINASE INHIBITORS<br/>[FR] IMIDAMIDES INHIBITEURS DE SPHINGOSINE KINASE
  申请人：UNIV VIRGINIA

  公开号：WO2011020116A1

  公开（公告）日：2011-02-17

  Imidamide (amidine) analogs that can inhibit the activity of sphingosine kinase 1 and sphingosine kinase 2 (SphKl & SphK2) are provided. The compounds can prevent angiogenesis in tumors.