(E)-1-(2-methoxyphenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one | 1189129-52-9

• 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)-1-(2-methoxyphenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
• 英文别名: 4-(Trifluoromethyl)-2'-methoxychalcone；(E)-1-(2-methoxyphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
• CAS: 1189129-52-9
• 化学式: C₁₇H₁₃F₃O₂
• 分子量: 306.284
• InChiKey: ZXIWVMHUOOBDMQ-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2'-甲氧基苯乙酮 、 对三氟甲基苯甲醛 在 lithium hydroxide monohydrate 作用下， 以 乙醇 为溶剂， 反应 2.17h， 以79%的产率得到(E)-1-(2-methoxyphenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Novel Chalcone Derivatives as Potent Nrf2 Activators in Mice and Human Lung Epithelial Cells

  摘要：

  Nrf2-mediated activation of antioxidant response element is a central part of molecular mechanisms governing the protective function of phase II detoxification and antioxidant enzymes against carcinogenesis, oxidative stress, and inflammation. Nrf2 is sequestered in the cytoplasm by its repressor, Keap1. We have designed and synthesized novel chalcone derivatives as Nrf2 activators. The potency of these compounds was measured by the expression of Nrf2 dependent antioxidant genes GCLM, NQO1, and HO1 in human lung epithelial cells, while the cytotoxicity was analyzed using MTT assay. In vivo potency of identified lead compounds to activate Nrf2 was evaluated using a mouse model. Our studies showed 2-trifluoromethyl-2'-methoxychalone (2b) to be a potent activator of Nrf2, both in vitro and in mice. Additional experiments showed that the activation of Nrf2 by this compound is independent of reactive oxygen species or redox changes. We have discussed a quantitative structure-activity relationship and proposed a possible mechanism of Nrf2, activation.

  DOI：

  10.1021/jm2002348

文献信息

• CHALCONE DERIVATIVES AS NRF2 ACTIVATORS
  申请人：Biswal Shyam

  公开号：US20140088052A1

  公开（公告）日：2014-03-27

  Compounds and methods for treating or preventing a disease, disorder or condition associated with an Nrf2-regulated pathway, including those associated with an autoimmune disease, comorbidity associated with diabetes, such as retinopathy and nephropathy, bone marrow transplant for leukemia and related cancers, bone marrow deficiencies, inborn errors of metabolism, and other immune disorders, oxidative stress, respiratory infection, ischemia, neurodegenerative disorders, radiation injury, neutropenia caused by chemotherapy, autoimmunity, and congenital neutropenic disorders, and for restoring a corticosteroid responsiveness, in a subject are provided.
• [EN] CHALCONE DERIVATIVES AS NRF2 ACTIVATORS<br/>[FR] DÉRIVÉS DE CHALCONE EN TANT QU'ACTIVATEURS DE NRF2
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2012116362A2

  公开（公告）日：2012-08-30

  Compounds and methods for treating or preventing a disease, disorder or condition associated with an Nrf2-regulated pathway, including those associated with an autoimmune disease, comorbidity associated with diabetes, such as retinopathy and nephropathy, bone marrow transplant for leukemia and related cancers, bone marrow deficiencies, inborn errors of metabolism, and other immune disorders, oxidative stress, respiratory infection, ischemia, neurodegenerative disorders, radiation injury, neutropenia caused by chemotherapy, autoimmunity, and congenital neutropenic disorders, and for restoring a corticosteroid responsiveness, in a subject are provided.
• Novel Chalcone Derivatives as Potent Nrf2 Activators in Mice and Human Lung Epithelial Cells
  作者：Vineet Kumar、Sarvesh Kumar、Mohammad Hassan、Hailong Wu、Rajesh K. Thimmulappa、Amit Kumar、Sunil K. Sharma、Virinder S. Parmar、Shyam Biswal、Sanjay V. Malhotra

  DOI：10.1021/jm2002348

  日期：2011.6.23

  Nrf2-mediated activation of antioxidant response element is a central part of molecular mechanisms governing the protective function of phase II detoxification and antioxidant enzymes against carcinogenesis, oxidative stress, and inflammation. Nrf2 is sequestered in the cytoplasm by its repressor, Keap1. We have designed and synthesized novel chalcone derivatives as Nrf2 activators. The potency of these compounds was measured by the expression of Nrf2 dependent antioxidant genes GCLM, NQO1, and HO1 in human lung epithelial cells, while the cytotoxicity was analyzed using MTT assay. In vivo potency of identified lead compounds to activate Nrf2 was evaluated using a mouse model. Our studies showed 2-trifluoromethyl-2'-methoxychalone (2b) to be a potent activator of Nrf2, both in vitro and in mice. Additional experiments showed that the activation of Nrf2 by this compound is independent of reactive oxygen species or redox changes. We have discussed a quantitative structure-activity relationship and proposed a possible mechanism of Nrf2, activation.