3,4-dibromo-2,5-dihydro-1-(ethylphenyl)-1H-pyrrole-2,5-dione | 92751-35-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,4-dibromo-2,5-dihydro-1-(ethylphenyl)-1H-pyrrole-2,5-dione
• 英文别名: 3,4-dibromo-1-phenethyl-1H-pyrrole-2,5-dione；Pyrrole-2,5-dione, 3,4-dibromo-1-(2-phenylethyl)-；3,4-dibromo-1-(2-phenylethyl)pyrrole-2,5-dione
• CAS: 92751-35-4
• 化学式: C₁₂H₉Br₂NO₂
• 分子量: 359.017
• InChiKey: IOLRZTMTASEVCI-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C
• 沸点：
  393.3±42.0 °C(Predicted)
• 密度：
  1.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dibromo-2,5-dihydro-1-(ethylphenyl)-1H-pyrrole-2,5-dione 在 palladium on activated charcoal 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 3,4-Bis-(5-diethoxymethyl-furan-2-yl)-1-phenethyl-pyrrole-2,5-dione
  参考文献：
  名称：

  取代的双（杂芳基）马来酰亚胺的合成

  摘要：

  描述了具有潜在抗糖尿病特性的取代的双（呋喃-2-基），双（呋喃-3-基）和双（噻吩-2-基）马来酰亚胺。作为关键步骤，它们的合成涉及各种硼衍生物与二碘亚胺之间的铃木交叉偶联。因此，可以制备各种取代的对称和非对称马来酰亚胺衍生物。

  DOI：

  10.1016/j.tet.2005.03.016
• 作为产物：
  描述：

  二溴马来酸 、 2-苯乙胺 以 溶剂黄146 为溶剂， 以59%的产率得到3,4-dibromo-2,5-dihydro-1-(ethylphenyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Development of antiproliferative phenylmaleimides that activate the unfolded protein response

  摘要：

  The current paper presents the synthesis and evaluation of a series of maleimides that were designed to inhibit the Cdc25 phosphatase by alkylation of catalytically essential cysteine residues. Although in HepB3 cell culture assays the analogues did exhibit antiproliferative IC50 values ranging from sub-micromolar to greater than 100 mu M, inhibition of Cdc25 through cysteine alkylation could not be demonstrated. It was also found that analysis using fluorescence activated cell sorting (FACS) following treatment with the most potent analogue (1t) did not provide data consistent with inhibition at one specific point in the cell cycle, as would be expected if Cdc25A were inhibited. Further studies with a subset of analogues resulted in a correlation of antiproliferative potencies with activation of the unfolded protein response (UPR). The UPR is a regulatory pathway that temporarily suspends protein production when misfolding of proteins occurs within the endoplastic reticulum(ER). In addition, ER chaperones that promote proper refolding become up-regulated. If cellular damage cannot be resolved by these mechanisms, then the UPR can initiate apoptosis. The current study indicates that these maleimide analogues lead to UPR activation, which is predictive of the selective antiproliferative activity of the series. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.04.057

文献信息

• Synthesis of substituted bis(heteroaryl)maleimides
  作者：Mathieu Dubernet、Virginie Caubert、Jérôme Guillard、Marie-Claude Viaud-Massuard

  DOI：10.1016/j.tet.2005.03.016

  日期：2005.5

  Substituted bis(fur-2-yl), bis(fur-3-yl) and bis(thien-2-yl) maleimides with potential antidiabetic properties are described. Their synthesis involves, as a key step, a Suzuki cross-coupling between various boron derivatives and the diiodomaleimides. Therefore, a wide range of substituted symmetric and non-symmetric maleimide derivatives can be prepared.

  描述了具有潜在抗糖尿病特性的取代的双（呋喃-2-基），双（呋喃-3-基）和双（噻吩-2-基）马来酰亚胺。作为关键步骤，它们的合成涉及各种硼衍生物与二碘亚胺之间的铃木交叉偶联。因此，可以制备各种取代的对称和非对称马来酰亚胺衍生物。
• Development of antiproliferative phenylmaleimides that activate the unfolded protein response
  作者：Ulrike Muus、Curtis Hose、Wei Yao、Teresa Kosakowska-Cholody、David Farnsworth、Marzena Dyba、George T. Lountos、David S. Waugh、Anne Monks、Terrence R. Burke Jr.

  DOI：10.1016/j.bmc.2010.04.057

  日期：2010.6.15

  The current paper presents the synthesis and evaluation of a series of maleimides that were designed to inhibit the Cdc25 phosphatase by alkylation of catalytically essential cysteine residues. Although in HepB3 cell culture assays the analogues did exhibit antiproliferative IC50 values ranging from sub-micromolar to greater than 100 mu M, inhibition of Cdc25 through cysteine alkylation could not be demonstrated. It was also found that analysis using fluorescence activated cell sorting (FACS) following treatment with the most potent analogue (1t) did not provide data consistent with inhibition at one specific point in the cell cycle, as would be expected if Cdc25A were inhibited. Further studies with a subset of analogues resulted in a correlation of antiproliferative potencies with activation of the unfolded protein response (UPR). The UPR is a regulatory pathway that temporarily suspends protein production when misfolding of proteins occurs within the endoplastic reticulum(ER). In addition, ER chaperones that promote proper refolding become up-regulated. If cellular damage cannot be resolved by these mechanisms, then the UPR can initiate apoptosis. The current study indicates that these maleimide analogues lead to UPR activation, which is predictive of the selective antiproliferative activity of the series. Published by Elsevier Ltd.