2-bromobenzimidazole | 1359858-96-0

• 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: 2-bromobenzimidazole
• 英文别名: 2-bromo-6-propylsulfonyl-1H-benzimidazole
• CAS: 1359858-96-0
• 化学式: C₁₀H₁₁BrN₂O₂S
• 分子量: 303.18
• InChiKey: YPQVOEHENLOHFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromobenzimidazole 、 2-联苯硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2-(2-phenylphenyl)-6-propylsulfonyl-1H-benzimidazole
  参考文献：
  名称：

  Design, synthesis and identification of novel benzimidazole derivatives as highly potent NPY Y5 receptor antagonists with attractive in vitro ADME profiles

  摘要：

  Optimization of our HTS hit 1, mainly focused on modification at the C-2 position of the benzimidazole core, is described. Elimination of the flexible and metabolically labile -S-CH2- part and utilization of less lipophilic pyridone substructure led to identification of novel NPY Y5 receptor antagonists 6, which have low to sub-nanomolar Y5 receptor binding affinity with improved CYP450 inhibition profiles, good solubilities and high metabolic stabilities. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.020
• 作为产物：
  描述：

  阿苯达唑 在 盐酸 、 水 、 间氯过氧苯甲酸 、 copper(I) bromide 、 sodium hydroxide 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 生成 2-bromobenzimidazole
  参考文献：
  名称：

  Design, synthesis and identification of novel benzimidazole derivatives as highly potent NPY Y5 receptor antagonists with attractive in vitro ADME profiles

  摘要：

  Optimization of our HTS hit 1, mainly focused on modification at the C-2 position of the benzimidazole core, is described. Elimination of the flexible and metabolically labile -S-CH2- part and utilization of less lipophilic pyridone substructure led to identification of novel NPY Y5 receptor antagonists 6, which have low to sub-nanomolar Y5 receptor binding affinity with improved CYP450 inhibition profiles, good solubilities and high metabolic stabilities. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.020

文献信息

• Identification of a novel and orally available benzimidazole derivative as an NPY Y5 receptor antagonist with in vivo efficacy
  作者：Yuusuke Tamura、Naoki Omori、Naoki Kouyama、Yuji Nishiura、Kyouhei Hayashi、Kana Watanabe、Yukari Tanaka、Takeshi Chiba、Hideo Yukioka、Hiroki Sato、Takayuki Okuno

  DOI：10.1016/j.bmcl.2012.09.025

  日期：2012.11

  Optimization of lead compound 2 is described, mainly focusing on modification at the C-2 position of the benzimidazole core. Replacement of the phenyl linker of 2 with saturated rings resulted in identification of compound 8b which combines high Y5 receptor binding affinity with a good ADME profile leading to in vivo efficacy. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, synthesis and identification of novel benzimidazole derivatives as highly potent NPY Y5 receptor antagonists with attractive in vitro ADME profiles
  作者：Yuusuke Tamura、Naoki Omori、Naoki Kouyama、Yuji Nishiura、Kyouhei Hayashi、Kana Watanabe、Yukari Tanaka、Takeshi Chiba、Hideo Yukioka、Hiroki Sato、Takayuki Okuno

  DOI：10.1016/j.bmcl.2012.07.020

  日期：2012.9

  Optimization of our HTS hit 1, mainly focused on modification at the C-2 position of the benzimidazole core, is described. Elimination of the flexible and metabolically labile -S-CH2- part and utilization of less lipophilic pyridone substructure led to identification of novel NPY Y5 receptor antagonists 6, which have low to sub-nanomolar Y5 receptor binding affinity with improved CYP450 inhibition profiles, good solubilities and high metabolic stabilities. (c) 2012 Elsevier Ltd. All rights reserved.