1-甲氧基-4-(3-(4-甲氧基苯基)-2-硝基-1-丙烯基)苯 | 156775-26-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 中文名称: 1-甲氧基-4-(3-(4-甲氧基苯基)-2-硝基-1-丙烯基)苯
• 英文名称: 1-methoxy-4-(3-(4-methoxyphenyl)-2-nitro-1-propenyl)benzene
• 英文别名: 1-methoxy-4-[3-(4-methoxyphenyl)-2-nitroprop-2-enyl]benzene
• CAS: 156775-26-7
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: DIJDOVZWVPMEKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-甲氧基-4-(3-(4-甲氧基苯基)-2-硝基-1-丙烯基)苯 在 铁粉 、 溶剂黄146 作用下， 反应 2.0h， 生成 文拉法辛杂质4
  参考文献：
  名称：

  Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents

  摘要：

  Structural derivatives of 4-MTA, an illegal amphetamine analogue have been previously shown to have anticancer effects in vitro. In this study we report the synthesis of a series of novel 1,3-bis(aryl)-2-nitro-1-propene derivatives related in structure to 4-MTA. A number of these compounds containing a classic nitrostyrene structure are shown to have antiproliferative activities in vitro in a range of malignant cell lines, particularly against Burkitt's lymphoma derived cell lines, whilst having no effect on 'normal' peripheral blood mononuclear cells. Such effects appear to be independent of the serotonin transporter, a high affinity target for amphetamines and independent of protein tyrosine phosphatases and tubulin dynamics both of which have been previously associated with nitrostyrene-induced cell death. We demonstrate that a number of these compounds induce caspase activation, PARP cleavage, chromatin condensation and membrane blebbing in a Burkitt's lymphoma derived cell line, consistent with these compounds inducing apoptosis in vitro. Although no specific target has yet been identified for the action of these compounds, the cell death elicited is potent, selective and worthy of further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.054
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 potassium fluoride 、 sodium tetrahydroborate 、 盐酸二甲胺 、 silica gel 、 环己胺 、 溶剂黄146 作用下， 以 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 反应 30.33h， 生成 1-甲氧基-4-(3-(4-甲氧基苯基)-2-硝基-1-丙烯基)苯
  参考文献：
  名称：

  Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents

  摘要：

  Structural derivatives of 4-MTA, an illegal amphetamine analogue have been previously shown to have anticancer effects in vitro. In this study we report the synthesis of a series of novel 1,3-bis(aryl)-2-nitro-1-propene derivatives related in structure to 4-MTA. A number of these compounds containing a classic nitrostyrene structure are shown to have antiproliferative activities in vitro in a range of malignant cell lines, particularly against Burkitt's lymphoma derived cell lines, whilst having no effect on 'normal' peripheral blood mononuclear cells. Such effects appear to be independent of the serotonin transporter, a high affinity target for amphetamines and independent of protein tyrosine phosphatases and tubulin dynamics both of which have been previously associated with nitrostyrene-induced cell death. We demonstrate that a number of these compounds induce caspase activation, PARP cleavage, chromatin condensation and membrane blebbing in a Burkitt's lymphoma derived cell line, consistent with these compounds inducing apoptosis in vitro. Although no specific target has yet been identified for the action of these compounds, the cell death elicited is potent, selective and worthy of further investigation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.054

文献信息

• Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines
  作者：Andrey A. Tabolin、Alexey V. Lesiv、Yulia A. Khomutova、Yulia V. Nelyubina、Sema L. Ioffe

  DOI：10.1016/j.tet.2009.03.082

  日期：2009.6

  A new approach toward the synthesis of 3-alpha-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines 1 from available 5,6-dihydro-4H-1,2-oxazine N-oxides 2 has been described. The key step of the process-the rearrangement of 3-alkiliden-2-siloxy-tetrahydro-1,2-oxazines 3 (ASENA)-was thoroughly investigated. Optimal experimental conditions were developed. A possible pathway of the ASENA rearrangement was proposed. (C) 2009 Elsevier Ltd. All rights reserved.