N-((2-methyl-1H-indol-3-yl)(naphthalen-2-yl)methyl)aniline | 1378490-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-((2-methyl-1H-indol-3-yl)(naphthalen-2-yl)methyl)aniline
• 英文别名: N-((2-methyl-1H-indol-3-yl)(naphthalen-2-yl)methyl)aniline；N-[(2-methyl-1H-indol-3-yl)-naphthalen-2-ylmethyl]aniline
• CAS: 1378490-49-3
• 化学式: C₂₆H₂₂N₂
• 分子量: 362.474
• InChiKey: QOAYZHCBPQVSGD-UHFFFAOYSA-N

物化性质

• 沸点：
  583.5±45.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 2-萘甲醛 、 苯胺 在 正癸酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以75%的产率得到 N-((2-methyl-1H-indol-3-yl)(naphthalen-2-yl)methyl)aniline
  参考文献：
  名称：

  Discovery of the First Irreversible Small Molecule Inhibitors of the Interaction between the Vitamin D Receptor and Coactivators

  摘要：

  The vitamin D receptor (VDR) is a nuclear hormone receptor that regulates cell proliferation, cell differentiation, and calcium homeostasis. The receptor is activated by vitamin D analogues that induce the disruption of VDR-corepressor binding and promote VDR-coactivator interactions. The interactions between VDR and coregulators are essential for VDR-mediated transcription. Small molecule inhibition of VDR-coregulator binding represents an alternative method to the traditional ligand-based approach in order to modulate the expression of VDR target genes. A high throughput fluorescence polarization screen that quantifies the inhibition of binding between VDR and a fluorescently labeled steroid receptor coactivator 2 peptide was applied to discover the new small molecule VDR-coactivator inhibitors, 3-indolylmethanamines. Structure-activity relationship studies with 3-indolylmethanamine analogues were used to determine their mode of VDR-binding and to produce the first VDR-selective and irreversible VDR-coactivator inhibitors with the ability to regulate the transcription of the human VDR target gene TRPV6.

  DOI：

  10.1021/jm300460c

文献信息

• Vitamin D receptor-coregulator inhibitors
  申请人：UWM Research Foundation, Inc.

  公开号：US10093653B2

  公开（公告）日：2018-10-09

  Described herein are compounds, pharmaceutical compositions and methods for inhibiting the expression of a vitamin D receptor target gene, inhibiting interactions between the vitamin D receptor and at least one vitamin D receptor coactivator, for treating cancer in a subject, and for inhibiting angiogenesis in a subject.

  本文描述了用于抑制维生素 D 受体靶基因表达、抑制维生素 D 受体与至少一种维生素 D 受体辅激活剂之间相互作用、治疗受试者癌症以及抑制受试者血管生成的化合物、药物组合物和方法。
• VITAMIN D RECEPTOR-COREGULATOR INHIBITORS
  申请人：Arnold Alexander E.

  公开号：US20140194472A1

  公开（公告）日：2014-07-10

  Described herein are compounds, pharmaceutical compositions and methods for inhibiting the expression of a vitamin D receptor target gene, inhibiting interactions between the vitamin D receptor and at least one vitamin D receptor coactivator, for treating cancer in a subject, and for inhibiting angiogenesis in a subject.
• US9416104B2
  申请人：——

  公开号：US9416104B2

  公开（公告）日：2016-08-16
• [EN] VITAMIN D RECEPTOR - COREGULATOR INHIBITORS<br/>[FR] INHIBITEURS DE RÉCEPTEUR DE VITAMINE D - CO-RÉGULATEUR
  申请人：UWM RES FOUNDATION INC

  公开号：WO2013032960A2

  公开（公告）日：2013-03-07

  Described herein are compounds, pharmaceutical compositions and methods for inhibiting the expression of a vitamin D receptor target gene, inhibiting interactions between the vitamin D receptor and at least one vitamin D receptor coactivator, for treating cancer in a subject, and for inhibiting angiogenesis in a subject.
• Discovery of the First Irreversible Small Molecule Inhibitors of the Interaction between the Vitamin D Receptor and Coactivators
  作者：Premchendar Nandhikonda、Wen Z. Lynt、Megan M. McCallum、Tahniyath Ara、Athena M. Baranowski、Nina Y. Yuan、Dana Pearson、Daniel D. Bikle、R. Kiplin Guy、Leggy A. Arnold

  DOI：10.1021/jm300460c

  日期：2012.5.24

  The vitamin D receptor (VDR) is a nuclear hormone receptor that regulates cell proliferation, cell differentiation, and calcium homeostasis. The receptor is activated by vitamin D analogues that induce the disruption of VDR-corepressor binding and promote VDR-coactivator interactions. The interactions between VDR and coregulators are essential for VDR-mediated transcription. Small molecule inhibition of VDR-coregulator binding represents an alternative method to the traditional ligand-based approach in order to modulate the expression of VDR target genes. A high throughput fluorescence polarization screen that quantifies the inhibition of binding between VDR and a fluorescently labeled steroid receptor coactivator 2 peptide was applied to discover the new small molecule VDR-coactivator inhibitors, 3-indolylmethanamines. Structure-activity relationship studies with 3-indolylmethanamine analogues were used to determine their mode of VDR-binding and to produce the first VDR-selective and irreversible VDR-coactivator inhibitors with the ability to regulate the transcription of the human VDR target gene TRPV6.