3-chloro-3-naphthalen-1-ylpropenal

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-chloro-3-naphthalen-1-ylpropenal
• 英文别名: β-Chlor-β-(α-naphthyl)-acrolein；(Z)-3-chloro-3-naphthalen-1-ylprop-2-enal
• 化学式: C₁₃H₉ClO
• 分子量: 216.667
• InChiKey: UEACXQNZNNPCJH-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-chloro-3-naphthalen-1-ylpropenal 、 肼甲酰亚胺酰胺一氯化氢 在 溶剂黄146 、 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 生成 2-[(3-chloro-3-naphthalen-1-ylprop-2-enylidene)amino]guanidine
  参考文献：
  名称：

  Synthesis and biological evaluation of guanylhydrazone coactivator binding inhibitors for the estrogen receptor

  摘要：

  Most patients with hormone-responsive breast cancer eventually develop resistance to traditional antiestrogens such as tamoxifen, and this has become a major obstacle in their treatment. We prepared and characterized the activity of a series of 16 guanylhydrazone small molecules that are designed to block estrogen receptor (ER) activity through a non-traditional mechanism, by directly interfering with coactivator binding to agonist-liganded ER. The inhibitory activity of these compounds was determined in cell-based transcription assays using ER-responsive reporter gene and mammalian two-hybrid assays. Several of the compounds gave IC50 values in the low micromolar range. Two secondary assays were used to confirm that these compounds were acting through the proposed non-traditional mode of estrogen inhibitory action and not as conventional antagonists at the ligand binding site. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.007
• 作为产物：
  描述：

  1-萘乙酮 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 水 、 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以16%的产率得到3-chloro-3-naphthalen-1-ylpropenal
  参考文献：
  名称：

  Synthesis and biological evaluation of guanylhydrazone coactivator binding inhibitors for the estrogen receptor

  摘要：

  Most patients with hormone-responsive breast cancer eventually develop resistance to traditional antiestrogens such as tamoxifen, and this has become a major obstacle in their treatment. We prepared and characterized the activity of a series of 16 guanylhydrazone small molecules that are designed to block estrogen receptor (ER) activity through a non-traditional mechanism, by directly interfering with coactivator binding to agonist-liganded ER. The inhibitory activity of these compounds was determined in cell-based transcription assays using ER-responsive reporter gene and mammalian two-hybrid assays. Several of the compounds gave IC50 values in the low micromolar range. Two secondary assays were used to confirm that these compounds were acting through the proposed non-traditional mode of estrogen inhibitory action and not as conventional antagonists at the ligand binding site. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.007

文献信息

• A simple approach to azirines containing an aldehyde functionality and their stabilization as palladium(II) complexes
  作者：Sulagna Brahma、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2005.07.086

  日期：2005.9

  A simple and useful method for the synthesis of azirines containing an aldehyde functionality, from open chain bromo/chloro-aldehydes at room temperature and their stabilization as palladium(II) complexes are reported.

  报道了一种在室温下由开链溴/氯醛合成含醛官能团的叠氮基的简单而有用的方法，该方法稳定了钯（II）配合物。
• Synthesis and biological evaluation of guanylhydrazone coactivator binding inhibitors for the estrogen receptor
  作者：Andrew L. LaFrate、Jillian R. Gunther、Kathryn E. Carlson、John A. Katzenellenbogen

  DOI：10.1016/j.bmc.2008.10.007

  日期：2008.12

  Most patients with hormone-responsive breast cancer eventually develop resistance to traditional antiestrogens such as tamoxifen, and this has become a major obstacle in their treatment. We prepared and characterized the activity of a series of 16 guanylhydrazone small molecules that are designed to block estrogen receptor (ER) activity through a non-traditional mechanism, by directly interfering with coactivator binding to agonist-liganded ER. The inhibitory activity of these compounds was determined in cell-based transcription assays using ER-responsive reporter gene and mammalian two-hybrid assays. Several of the compounds gave IC50 values in the low micromolar range. Two secondary assays were used to confirm that these compounds were acting through the proposed non-traditional mode of estrogen inhibitory action and not as conventional antagonists at the ligand binding site. (c) 2008 Elsevier Ltd. All rights reserved.