1-(4-acetylphenyl)-3,4-dibromo-1H-pyrrole-2,5-dione | 863886-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-acetylphenyl)-3,4-dibromo-1H-pyrrole-2,5-dione
• 英文别名: N-(4-acetyl-phenyl)-3,4-dibromo-maleimide；1-(4-acetylphenyl)-3,4-dibromopyrrole-2,5-dione
• CAS: 863886-52-6
• 化学式: C₁₂H₇Br₂NO₃
• 分子量: 373.0
• InChiKey: JIEKMTZCTHXXNB-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  435.6±45.0 °C(Predicted)
• 密度：
  2.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-acetylphenyl)-3,4-dibromo-1H-pyrrole-2,5-dione 、 水杨醛 在 silica-sulfuric acid 作用下， 以93%的产率得到3,4-dibromo-1-[4-[(E)-3-(2-hydroxyphenyl)prop-2-enoyl]phenyl]pyrrole-2,5-dione
  参考文献：
  名称：

  Silica sulfuric acid-catalyzed Claisen-Schmidt condensation of 1,3,4 trisubstituted pyrrole 2,5 dione to chalcones

  摘要：

  在无溶剂条件下，以二氧化硅-硫酸为催化剂，从 1-(4-乙酰基苯基)-3,4-二溴-1H-吡咯-2,5-二酮与各种取代的苯甲醛合成了一系列 11 种查尔酮。查耳酮的产率超过 90%。所有化合物均通过物理、光谱和元素分析进行了表征。

  DOI：

  10.1007/s11164-012-0553-6
• 作为产物：
  描述：

  N-(4-乙酰苯基)-2,5-马来酰亚胺 在 aluminum (III) chloride 、 溴 作用下， 反应 16.0h， 生成 1-(4-acetylphenyl)-3,4-dibromo-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of 1-(4-((E)-3-arylacryloyl) phenyl)-3,4-dibromo-1H-pyrrole-2,5-diones and screening for anti-Candida and antituberculosis activity

  摘要：

  A series of eleven 1-(4-((E)-3-arylacryloyl) phenyl)-3,4 dibromo-1H-pyrrole-2,5-diones (4'-aminochalcone-based dibromomaleimides) were synthesized using maleic anhydride and p-aminoacetophenone as starting material. Furthermore, there has been some additional work investigating the effect of these derivatives on biological activity. They were characterized using FTIR, H-1 NMR, C-13 NMR, ESI mass spectroscopy, and elemental analysis. The compounds show anti-Candida & antituberculosis activity.

  DOI：

  10.1007/s00044-011-9718-x

文献信息

• 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.