(E)-3-(3-Chloro-phenyl)-1-naphthalen-2-yl-propenone | 57221-65-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(3-Chloro-phenyl)-1-naphthalen-2-yl-propenone
• 英文别名: (E)-3-(3-chlorophenyl)-1-(2-naphthyl)prop-2-en-1-one；(E)-3-(3-chlorophenyl)-1-naphthalen-2-ylprop-2-en-1-one
• CAS: 57221-65-5
• 化学式: C₁₉H₁₃ClO
• 分子量: 292.765
• InChiKey: DHTNDUIYNLNTDG-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  (E)-3-(3-Chloro-phenyl)-1-naphthalen-2-yl-propenone 在 trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane 、 水 、 双氧水 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 以90%的产率得到
  参考文献：
  名称：

  Facile Epoxidation of α,β-Unsaturated Ketones with trans-3,5-Dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an Efficient Oxidant

  摘要：

  探索了以反式-3,5-二氢过氧-3,5-二甲基-1,2-二噁烷作为高效氧源在反式查尔酮环氧化反应中的应用。反应在室温下温和条件下于碱性溶液中进行，以优异的收率得到相应的环氧化物。

  DOI：

  10.1055/s-0030-1258996
• 作为产物：
  描述：

  3-氯苯甲醛 、 2-萘乙酮 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (E)-3-(3-Chloro-phenyl)-1-naphthalen-2-yl-propenone
  参考文献：
  名称：

  Naphthylchalcones induce apoptosis and caspase activation in a leukemia cell line: The relationship between mitochondrial damage, oxidative stress, and cell death

  摘要：

  In this study, we investigated the effects of 24 chalcone derivatives from 2-naphthylacetophenone toward a lymphoblastic leukemia cell line (L1210). Three compounds, called R7, R13, and R15, presented concentration- and time-dependent cytotoxicity and induced cellular death by apoptosis via mitochondrial injury and oxidative stress. The effects of these compounds appear to occur through different mechanisms because R13 and R7 induced a greater disturbance of mitochondrial potential, and all compounds induced disturbances of cellular ATP content and increased caspase-3 activity before cellular death. These compounds also interfered with antioxidant enzymes activities and GSH content through different mechanisms. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.025

文献信息

• Studies on cycloimmonium ylides: synthesis of some new 2,4,6-trisubstituted pyridines. 2
  作者：Ram S. Tewari、Suresh C. Chaturvedi、Dinesh K. Nagpal

  DOI：10.1021/je60086a032

  日期：1980.7
• TEWARI R. S.; CHATUROEDI S. C.; NAGPAL D. K., J- CHEM. AND ENG. DATA, 1980, 25, NO 3, 293-295
  作者：TEWARI R. S.、 CHATUROEDI S. C.、 NAGPAL D. K.

  DOI：——

  日期：——
• AL-ARAB, MOHAMMAD M., J. HETEROCYCL. CHEM., 26,(1989) N, C. 1665-1673
  作者：AL-ARAB, MOHAMMAD M.

  DOI：——

  日期：——
• Facile Epoxidation of α,β-Unsaturated Ketones with trans-3,5-Dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an Efficient Oxidant
  作者：Davood Azarifar、Kaveh Khosravi

  DOI：10.1055/s-0030-1258996

  日期：2010.11

  Application of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an efficient oxygen source has been explored in the epoxidation of trans-chalcones. The reactions proceed under mild conditions at room temperature in alkaline solution to afford the corresponding epoxides in excellent yields.

  探索了以反式-3,5-二氢过氧-3,5-二甲基-1,2-二噁烷作为高效氧源在反式查尔酮环氧化反应中的应用。反应在室温下温和条件下于碱性溶液中进行，以优异的收率得到相应的环氧化物。
• Naphthylchalcones induce apoptosis and caspase activation in a leukemia cell line: The relationship between mitochondrial damage, oxidative stress, and cell death
  作者：Evelyn Winter、Louise Domeneghini Chiaradia、Clarissa A.S. de Cordova、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.bmc.2010.09.025

  日期：2010.11

  In this study, we investigated the effects of 24 chalcone derivatives from 2-naphthylacetophenone toward a lymphoblastic leukemia cell line (L1210). Three compounds, called R7, R13, and R15, presented concentration- and time-dependent cytotoxicity and induced cellular death by apoptosis via mitochondrial injury and oxidative stress. The effects of these compounds appear to occur through different mechanisms because R13 and R7 induced a greater disturbance of mitochondrial potential, and all compounds induced disturbances of cellular ATP content and increased caspase-3 activity before cellular death. These compounds also interfered with antioxidant enzymes activities and GSH content through different mechanisms. (C) 2010 Elsevier Ltd. All rights reserved.