4,7-dihydroxybenzo[d]imidazole monohydrobromide | 7711-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4,7-dihydroxybenzo[d]imidazole monohydrobromide
• 英文别名: 1H-benzimidazole-4,7-diol; hydrobromide；1H-Benzimidazol-4,7-diol; Hydrobromid；1H-Benzo[d]imidazole-4,7-diol hydrobromide；1H-benzimidazole-4,7-diol;hydrobromide
• CAS: 7711-57-1
• 化学式: BrH*C₇H₆N₂O₂
• 分子量: 231.049
• InChiKey: VZVJUMJMFBTVLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  12
• 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：
  69.1
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3,6-dimethoxybenzene-1,2-diamine hydrochloride 在 氢溴酸 作用下， 生成 4,7-dihydroxybenzo[d]imidazole monohydrobromide
  参考文献：
  名称：

  Syntheses of Dimethoxybenzimidazoles, Dihydroxybenzimidazoles and Imidazo-p-benzoquinones

  摘要：

  DOI：

  10.1021/jo01092a017

文献信息

• Benzimidazole-4,7-diones as Inhibitors of Protozoal ( Toxoplasma gondii ) Purine Nucleoside Phosphorylase
  作者：Frédéric Alvarez、Arnaud Ghérardi、Pascal Nebois、Marie-Elizabeth Sarciron、Anne-Françoise Pétavy、Nadia Walchshofer

  DOI：10.1016/s0960-894x(02)00064-1

  日期：2002.3

  Ben zimidazole-4,7-diones derivatives substituted at 1- and/or 2-position have been synthetized and tested as inhibitors of purine nucleoside phosphorylase (PNP), isolated from two strains of Toxoplasma gondii (RH and ME 49). They were identified as inhibitors of both enzymes. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.
• Haarfärbemittel
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：EP0004368B1

  公开（公告）日：1981-11-04
• Syntheses of Dimethoxybenzimidazoles, Dihydroxybenzimidazoles and Imidazo-p-benzoquinones
  作者：LESTER WEINBERGER、ALLAN R. DAY

  DOI：10.1021/jo01092a017

  日期：1959.10
• 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.