1,3-Bis<(4-methylsulfanyl)phenyl>propan-2-on | 34252-97-6

• 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: 1,3-Bis<(4-methylsulfanyl)phenyl>propan-2-on
• 英文别名: 1,3-di(4-methylthiophenyl)-2-propanone；1,3-Di-p-methylthiophenylpropan-2-on；1,3-bis(4-methylsulfanylphenyl)propan-2-one
• CAS: 34252-97-6
• 化学式: C₁₇H₁₈OS₂
• 分子量: 302.461
• InChiKey: ZOXIHYKCYDRSLB-UHFFFAOYSA-N

物化性质

• 沸点：
  451.2±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,3-Bis<(4-methylsulfanyl)phenyl>propan-2-on 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 生成 1,3-Bis<(4-methansulfonyl)phenyl>propan-2-on
  参考文献：
  名称：

  酰基芳基亚硝胺。第四部分 芳烃参与N-亚硝基乙酰苯胺及其在苯中的m-和p-叔丁基-，o-，m-和p-氯衍生物的分解

  摘要：

  的分解Ñ -nitrosoacetanilide，米和- p -t -丁基- ，米- ，p - ，和ö氯代Ñ -nitrosoacetanilides苯，等溶剂，在arynophiles如蒽及其衍生物，2的存在除最后命名的亚硝酰胺外，， 3，4，5-四芳基环戊二烯酮和1，3-二苯基异苯并呋喃得到的芳烃加成物与所用的苯胺相对应，产率为4-82％。这些亚硝酰胺均未在15°下与呋喃产生相应的芳烃加成物。对叔丁基N-亚硝基乙酰苯胺在四苯基环戊二烯酮的存在下得到6-叔丁基-1,2,3,4-四苯基萘，而不是异构的1-（对叔丁基-苯基）-2,3,4-三苯基萘，因此表明二齿动物而不是单齿动物的中介。在两种情况下，允许成对的嗜碱细胞竞争（a）竞争纯苯炔（b）竞争由N-亚硝基乙酰苯胺生产的中间体的竞争实验得出几乎相同的结果，表明情况（b）也涉及苯甲醛。一种涉及去除质子邻位的机制-提出了在中间体苯重氮乙酸酯中的

  DOI：

  10.1039/j29710001996
• 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 26.33h， 生成 1,3-Bis<(4-methylsulfanyl)phenyl>propan-2-on
  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。
• Reichardt, Christian; Schaefer, Gerhard; Milart, Piotr, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 1, p. 97 - 118
  作者：Reichardt, Christian、Schaefer, Gerhard、Milart, Piotr

  DOI：——

  日期：——
• REICHARDI, CHRISTIAN;SCHAFER, GERHARD;MILART, PIOTR, COLLECT. CZECHOSL. CHEM. COMMUN., 55,(1990) N, C. 97-118
  作者：REICHARDI, CHRISTIAN、SCHAFER, GERHARD、MILART, PIOTR

  DOI：——

  日期：——
• 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.
• Acylarylnitrosamines. Part IV. Aryne participation in decompositions of N-nitrosoacetanilide and its m- and p-t-butyl-, o-, m-, and p-chloro-derivatives in benzene
  作者：D. L. Brydon、J. I. G. Cadogan、J. Cook、M. J. P. Harger、J. T. Sharp

  DOI：10.1039/j29710001996

  日期：——

  pairs of arynophiles were allowed to compete (a) for authentic benzyne (b) for the intermediate produced by N-nitrosoacetanilide gave almost identical results in both cases, indicating that benzyne is involved in case (b) also. A mechanism involving removal of a proton ortho- to the diazonium function in the intermediate benzenediazonium acetate is proposed and an explanation for the anomalous behaviour

  的分解Ñ -nitrosoacetanilide，米和- p -t -丁基- ，米- ，p - ，和ö氯代Ñ -nitrosoacetanilides苯，等溶剂，在arynophiles如蒽及其衍生物，2的存在除最后命名的亚硝酰胺外，， 3，4，5-四芳基环戊二烯酮和1，3-二苯基异苯并呋喃得到的芳烃加成物与所用的苯胺相对应，产率为4-82％。这些亚硝酰胺均未在15°下与呋喃产生相应的芳烃加成物。对叔丁基N-亚硝基乙酰苯胺在四苯基环戊二烯酮的存在下得到6-叔丁基-1,2,3,4-四苯基萘，而不是异构的1-（对叔丁基-苯基）-2,3,4-三苯基萘，因此表明二齿动物而不是单齿动物的中介。在两种情况下，允许成对的嗜碱细胞竞争（a）竞争纯苯炔（b）竞争由N-亚硝基乙酰苯胺生产的中间体的竞争实验得出几乎相同的结果，表明情况（b）也涉及苯甲醛。一种涉及去除质子邻位的机制-提出了在中间体苯重氮乙酸酯中的