(E)-9-(2-nitroprop-1-en-1-yl)anthracene | 125536-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (E)-9-(2-nitroprop-1-en-1-yl)anthracene
• 英文别名: 9-[(E)-2-nitroprop-1-enyl]anthracene
• CAS: 125536-81-4
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: UYBCRERGMQETMT-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-9-(2-nitroprop-1-en-1-yl)anthracene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 42.0h， 生成 1-(9-蒽基)-2-氨基丙烷
  参考文献：
  名称：

  The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands

  摘要：

  The lipophilicity of a set of 5-HT2A ligands was determined using immobilized-artificial-membrane chromatography, a method that generates values well correlated with octanol-water partition coefficients. For agonists, a highly significant linear correlation was observed between binding affinity and lipophilicity. For ligands exhibiting partial agonist or antagonist properties, the lipophilicity was consistently higher than would be expected for an agonist of comparable affinity. The results suggest a possible method for distinguishing agonists from antagonists in high-throughput screening when a direct assay for functional activity is either unavailable or impractical. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.033
• 作为产物：
  描述：

  (Z)-9-(2-nitropropenyl)anthracene 以 苯 为溶剂， 反应 2.0h， 生成 (E)-9-(2-nitroprop-1-en-1-yl)anthracene
  参考文献：
  名称：

  Becker, Hans-Dieter; Skelton, Brian W.; Soerensen, Henrik, Australian Journal of Chemistry, 1989, vol. 42, # 4, p. 593 - 602

  摘要：

  DOI：

文献信息

• Synthesis, Antiproliferative and Pro-Apoptotic Effects of Nitrostyrenes and Related Compounds in Burkitt's Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、Darren Fayne、James P. McKeown、Thomas McCabe、Brendan Twamley、Clive Williams、Mary J. Meegan

  DOI：10.2174/1573406413666171002123907

  日期：2018.2.6

  identified as a lead target structure for the development of particularly effective compounds targeting Burkitt's lymphoma (BL). OBJECTIVES The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt's lymphoma (BL). METHODS A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions.

  背景技术淋巴细胞癌（淋巴瘤）约占全世界恶性疾病的12％。硝基苯乙烯支架被认为是开发针对Burkitt淋巴瘤（BL）的特别有效的化合物的主要靶标结构。目的目前的研究目的是合成一组硝基苯乙烯化合物并评估其在伯基特氏淋巴瘤（BL）中的活性。方法使用Henry Knoevenagel缩合反应设计和合成一组结构变化的化合物。单晶X射线分析证实了这些新颖结构的六个实例的E构型。还研究了许多与硝基苯乙烯有关的化合物，包括1，3-双（芳基）-2-硝基丙烯与含有硝基乙烯基药效团的杂环支架，例如3-硝基-2-苯基-2H-色烯。使用BL细胞系EBV-MUTU-1和EBV + DG-75（耐化学性）评估化合物的抗增殖活性，以建立初步的结构活性关系。结果成功建立了具有优化的硝基苯乙烯骨架和3-硝基-2-苯基-2Hchromne结构的铅化合物，在MUTU-1细胞中的典型IC50值分别为0.45 µM和0.47 µM，
• Design, Synthesis and Biochemical Evaluation of Novel Ethanoanthracenes and Related Compounds to Target Burkitt’s Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、James P. McKeown、John E. O’Brien、Brendan Twamley、Darren Fayne、D. Clive Williams、Mary J. Meegan

  DOI：10.3390/ph13010016

  日期：——

  Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG-75. Structural modifications were achieved by Diels-Alder

  淋巴瘤（淋巴系统癌）占全世界恶性疾病的12％。伯基特氏淋巴瘤（BL）是非霍奇金淋巴瘤的一种罕见形式，其癌症始于免疫B细胞。我们报告了9,10-dihydro-9,10-ethanananthracene基化合物与抗抑郁药Maprotiline对BL细胞系MUTU-1和DG-75结构相关的化合物的合成和抗增殖活性的初步研究。通过使9-（2-硝基乙烯基）蒽核心与许多亲二烯体包括马来酸酐，马来酰亚胺，丙烯腈和苯炔的狄尔斯-阿尔德反应进行结构修饰。在BL细胞系EBV- MUTU-1和EBV + DG-75（耐化学性）中评估了这些化合物的抗增殖活性。最有效的化合物13j，15、16a，16b，16c，图16d和19a显示的相对于BL细胞系EBV- MUTU-1的IC50值在0.17–0.38μM范围内，相对于耐化学性BL细胞系EBV + DG-75的IC50值在0.45–0.78μM范围内。化合物1
• The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands
  作者：Matthew A. Parker、Deborah M. Kurrasch、David E. Nichols

  DOI：10.1016/j.bmc.2008.02.033

  日期：2008.4

  The lipophilicity of a set of 5-HT2A ligands was determined using immobilized-artificial-membrane chromatography, a method that generates values well correlated with octanol-water partition coefficients. For agonists, a highly significant linear correlation was observed between binding affinity and lipophilicity. For ligands exhibiting partial agonist or antagonist properties, the lipophilicity was consistently higher than would be expected for an agonist of comparable affinity. The results suggest a possible method for distinguishing agonists from antagonists in high-throughput screening when a direct assay for functional activity is either unavailable or impractical. (c) 2008 Elsevier Ltd. All rights reserved.
• Becker, Hans-Dieter; Skelton, Brian W.; Soerensen, Henrik, Australian Journal of Chemistry, 1989, vol. 42, # 4, p. 593 - 602
  作者：Becker, Hans-Dieter、Skelton, Brian W.、Soerensen, Henrik、White, Allan H.

  DOI：——

  日期：——