2-N-formylamino-1,3-di(4-methylthiophenyl)propane | 1236220-52-2

• 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: 2-N-formylamino-1,3-di(4-methylthiophenyl)propane
• 英文别名: N-formyl-1,3-bis(4-methylthiophenyl)-2-propanamine；N-[1,3-bis(4-methylsulfanylphenyl)propan-2-yl]formamide
• CAS: 1236220-52-2
• 化学式: C₁₈H₂₁NOS₂
• 分子量: 331.503
• InChiKey: AOHIFHMTRIPJAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-N-formylamino-1,3-di(4-methylthiophenyl)propane 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 11.0h， 生成 2-N-ethylamino-1,3-di(4-methylthiophenyl)propane
  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-(methylthio)-β-nitrostyrene 在 potassium fluoride 、 sodium tetrahydroborate 、 盐酸二甲胺 、 silica gel 、 铁粉 、 溶剂黄146 作用下， 以 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 反应 31.33h， 生成 2-N-formylamino-1,3-di(4-methylthiophenyl)propane 、 4-(4-methylthiobenzyl)-5-(4-methylthiophenyl)pyrimidine
  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

• Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted α-alkylthioamphetamines
  作者：Suzanne M. Cloonan、John J. Keating、Desmond Corrigan、John E. O’Brien、Pierce V. Kavanagh、D. Clive Williams、Mary J. Meegan

  DOI：10.1016/j.bmc.2010.04.022

  日期：2010.6.1

  drugs often contain byproducts of uncontrolled, illegal clandestine synthetic processes. We report the isolation and structural identification of a number of novel pyridines, dihydropyridone and N,N-di(1-aryl-2-propyl) amines as route-specific byproducts associated with clandestine synthesis of 4-MTA and related amphetamines. We report the in vitro cytotoxicity of 4-MTA, its synthesis byproducts together

  4-甲硫基苯丙胺（4-MTA）被认为是一种3,4-亚甲二氧基甲基苯丙胺（MDMA）滥用药物。这种苯丙胺类药物通常含有不受控制的非法秘密合成过程的副产物。我们报告了许多新型吡啶，二氢吡啶酮和N，N的分离和结构鉴定-二（1-芳基-2-丙基）胺是与4-MTA和相关苯丙胺的秘密合成有关的途径特定的副产物。我们报告了4-MTA的体外细胞毒性，其合成副产物与一些结构相关的硫取代的α-烷基苯乙胺在过度表达人单胺转运蛋白的细胞系以及主要神经元细胞系模型和多巴胺能神经母细胞瘤细胞系中。在药理定义的浓度范围内，发现4-MTA以及许多其他与结构相关的苯丙胺衍生物和合成杂质对这些细胞具有细胞毒性，这表明4-MTA在体外是细胞毒性剂，因此可能具有神经毒性剂的潜力。体内。
• Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents
  作者：Yvonne M. McNamara、Suzanne M. Cloonan、Andrew J.S. Knox、John J. Keating、Stephen G. Butler、Günther H. Peters、Mary J. Meegan、D. Clive Williams

  DOI：10.1016/j.bmc.2010.11.054

  日期：2011.2

  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.