5,6-dibromo-1H-benzo[d]imidazole-4,7-dione | 26573-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-dibromo-1H-benzo[d]imidazole-4,7-dione
• 英文别名: 5,6-dibromo-benzimidazole-4,7-dione；5,6-dibromobenzimidazole-4,7-dione；5,6-dibromo-1H-benzoimidazole-4,7-dione；5,6-Dibrom-4,7-benzimidazoldion；5,6-dibromo-1H-benzimidazole-4,7-dione
• CAS: 26573-35-3
• 化学式: C₇H₂Br₂N₂O₂
• 分子量: 305.913
• InChiKey: WHRDOPKCVUZBMR-UHFFFAOYSA-N

物化性质

• 熔点：
  250 °C (decomp)
• 沸点：
  467.3±45.0 °C(Predicted)
• 密度：
  2.574±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dibromo-1H-benzo[d]imidazole-4,7-dione 、 2-甲基氮丙啶 以 乙二醇二甲醚 为溶剂， 以38%的产率得到5-bromo-6-(methylaziridinyl)benzimidazole-4,7-dione
  参考文献：
  名称：

  具有潜在抗肿瘤活性的杂环醌。2.一些苯并咪唑-4，7-二酮衍生物的合成和抗肿瘤活性。

  摘要：

  已经合成了一系列在苯并咪唑环的1、2、5和6位带有取代基的苯并咪唑-4,7-二酮衍生物，并在体内测试了其对P388白血病的抗肿瘤活性。然而，一些合成的化合物显示出显着的抗肿瘤活性，并伴有高毒性。化合物7、18和27在此系列中显示出最高的抗肿瘤活性，而17、19和22几乎没有活性。这些醌的一些假设的生物学前体没有抗肿瘤活性。讨论了一些构效关系。

  DOI：

  10.1021/jm00396a041
• 作为产物：
  描述：

  4,7-dihydroxybenzo[d]imidazole monohydrobromide 在 sodium perborate 、 氢溴酸 作用下， 以 水 为溶剂， 以49%的产率得到5,6-dibromo-1H-benzo[d]imidazole-4,7-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-arylamino-1H-benzo[d]imidazole-4,7-diones as inhibitor of endothelial cell proliferation

  摘要：

  5-Arylamino-1H-benzo[d]imidazole-4,7-diones were synthesized and tested for their inhibitory activities on the proliferation of human umbilical vein endothelial cells (HUVECs) and the smooth muscle cells (SMCs). Among them, several 1H-benzo[d]imidazole-4,7-diones exhibited the selective antiproliferative activity on the HUVECs. Further mechanistic study revealed that the inhibitory effect of one representative 1H-benzo[d]imidazole-4,7-dione 2b on HUVEC proliferation was mediated by the activation of p38 signaling pathway in the HUVECs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.059

文献信息

• Synthesis and biological evaluation of benzimidazole-4,7-diones that inhibit vascular smooth muscle cell proliferation
  作者：Sung-Yu Hong、Kwang-Hoe Chung、Hea-Jung You、Ik Hwa Choi、Mi Jin Chae、Ja-Young Han、Ok-Jai Jung、Soo-Jung Kang、Chung-Kyu Ryu

  DOI：10.1016/j.bmcl.2004.04.051

  日期：2004.7

  A series of 6-arylamino-5-chloro-benzimidazole-4,7-diones were synthesized and tested for their inhibitory activity on the rat aortic smooth muscle cell (RAoSMC) proliferation. Among them, 6-arylamino-5-chloro-2-methyl-benzimidazole-4,7-diones exhibited potent antiproliferative activity. Benzimidazole-4,7-dione 2c activated SAPK/JNK signaling pathway in the RAoSMCs. (C) 2004 Elsevier Ltd. All rights reserved.
• ANTONINI, IPPOLITO;CLAUDI, FRANCESCO;CRISTALLI, GLORIA;FRANCHETTI, PALMAR+, J. MED. CHEM., 31,(1988) N 1, 260-264
  作者：ANTONINI, IPPOLITO、CLAUDI, FRANCESCO、CRISTALLI, GLORIA、FRANCHETTI, PALMAR+

  DOI：——

  日期：——
• Heterocyclic quinones with potential antitumor activity. 2. Synthesis and antitumor activity of some benzimidazole-4,7-dione derivatives
  作者：Ippolito Antonini、Francesco Claudi、Gloria Cristalli、Palmarisa Franchetti、Mario Grifantini、Sante Martelli

  DOI：10.1021/jm00396a041

  日期：1988.1

  series of benzimidazole-4,7-dione derivatives, bearing substituents at positions 1, 2, 5, and 6 of the benzimidazole ring, has been synthesized and tested for antitumor activity in vivo on P388 leukemia. Some of the synthesized compounds show significant antitumor activity, associated with high toxicity, however. Compounds 7, 18, and 27 show the highest antitumor activity in this series, whereas 17

  已经合成了一系列在苯并咪唑环的1、2、5和6位带有取代基的苯并咪唑-4,7-二酮衍生物，并在体内测试了其对P388白血病的抗肿瘤活性。然而，一些合成的化合物显示出显着的抗肿瘤活性，并伴有高毒性。化合物7、18和27在此系列中显示出最高的抗肿瘤活性，而17、19和22几乎没有活性。这些醌的一些假设的生物学前体没有抗肿瘤活性。讨论了一些构效关系。
• Synthesis and biological evaluation of 5-arylamino-1H-benzo[d]imidazole-4,7-diones as inhibitor of endothelial cell proliferation
  作者：Kwang-Hoe Chung、Sung-Yu Hong、Hea-Jung You、Rae-Eun Park、Chung-Kyu Ryu

  DOI：10.1016/j.bmc.2006.05.059

  日期：2006.9

  5-Arylamino-1H-benzo[d]imidazole-4,7-diones were synthesized and tested for their inhibitory activities on the proliferation of human umbilical vein endothelial cells (HUVECs) and the smooth muscle cells (SMCs). Among them, several 1H-benzo[d]imidazole-4,7-diones exhibited the selective antiproliferative activity on the HUVECs. Further mechanistic study revealed that the inhibitory effect of one representative 1H-benzo[d]imidazole-4,7-dione 2b on HUVEC proliferation was mediated by the activation of p38 signaling pathway in the HUVECs. (c) 2006 Elsevier Ltd. All rights reserved.