5,6-dichloro-1H-benzo[d]imidazole-4,7-dione | 34674-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-dichloro-1H-benzo[d]imidazole-4,7-dione
• 英文别名: 5,6-dichloro-benzimidazole-4,7-dione；5,6-dichloro-1H-benzoimidazole-4,7-dione；5,6-Dichloro-1h-benzimidazole-4,7-dione
• CAS: 34674-41-4
• 化学式: C₇H₂Cl₂N₂O₂
• 分子量: 217.011
• InChiKey: GAVOHPUJZLSPPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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-dichloro-1H-benzo[d]imidazole-4,7-dione 、 3,4-二氟苯胺 以 乙醇 为溶剂， 反应 5.0h， 以67%的产率得到6-chloro-5-(3,4-difluoroanilino)-1H-benzimidazole-4,7-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of benzimidazole-4,7-diones that inhibit vascular smooth muscle cell proliferation

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.04.051
• 作为产物：
  描述：

  4,7-二甲氧基-(9ci)-1H-苯并咪唑 在 盐酸 、 硝酸 作用下， 反应 0.5h， 以52%的产率得到5,6-dichloro-1H-benzo[d]imidazole-4,7-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of benzimidazole-4,7-diones that inhibit vascular smooth muscle cell proliferation

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.04.051

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.
• 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.