4-(1H-benzimidazol-2-ylamino)phenol | 446845-17-6

• 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-(1H-benzimidazol-2-ylamino)phenol
• CAS: 446845-17-6
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: UNABYEWLYJWLCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.9
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴-4-氯吡啶 、 4-(1H-benzimidazol-2-ylamino)phenol 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 N-[4-(3-bromopyridin-4-yl)oxyphenyl]-1H-benzimidazol-2-amine
  参考文献：
  名称：

  Discovery of selective biaryl ethers as PDE10A inhibitors: Improvement in potency and mitigation of Pgp-mediated efflux

  摘要：

  We report the discovery of a novel series of biaryl ethers as potent and selective PDE10A inhibitors. Structure-activity studies improved the potency and decreased Pgp-mediated efflux found in the initial compound 4. X-ray crystallographic studies revealed two novel binding modes to the catalytic site of the PDE10A enzyme. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.078
• 作为产物：
  描述：

  2-氯苯并咪唑 、 对氨基苯酚 在 盐酸 作用下， 以 乙醇 为溶剂， 以72%的产率得到4-(1H-benzimidazol-2-ylamino)phenol
  参考文献：
  名称：

  Discovery of selective biaryl ethers as PDE10A inhibitors: Improvement in potency and mitigation of Pgp-mediated efflux

  摘要：

  We report the discovery of a novel series of biaryl ethers as potent and selective PDE10A inhibitors. Structure-activity studies improved the potency and decreased Pgp-mediated efflux found in the initial compound 4. X-ray crystallographic studies revealed two novel binding modes to the catalytic site of the PDE10A enzyme. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.078

文献信息

• An efficient method to access 2-substituted benzimidazoles under solvent-free conditions
  作者：Ping Lan、F. Anthony Romero、Threshia S. Malcolm、Benjamin D. Stevens、Dariusz Wodka、Gergely M. Makara

  DOI：10.1016/j.tetlet.2008.01.100

  日期：2008.3

  An expeditious method to access 2-substituted benzimidazoles was developed. Both aromatic (phenols, anilines, and thiophenols) and alkyl nucleophiles (amines and thiols) react with 2-methylsulfonyl benzimidazole under solvent-free conditions to generate a variety of 2-substituted benzimidazoles. (c) 2008 Elsevier Ltd. All rights reserved.
• Discovery of selective biaryl ethers as PDE10A inhibitors: Improvement in potency and mitigation of Pgp-mediated efflux
  作者：Robert M. Rzasa、Essa Hu、Shannon Rumfelt、Ning Chen、Kristin L. Andrews、Samer Chmait、James R. Falsey、Wenge Zhong、Adrie D. Jones、Amy Porter、Steven W. Louie、Xiaoning Zhao、James J.S. Treanor、Jennifer R. Allen

  DOI：10.1016/j.bmcl.2012.10.078

  日期：2012.12

  We report the discovery of a novel series of biaryl ethers as potent and selective PDE10A inhibitors. Structure-activity studies improved the potency and decreased Pgp-mediated efflux found in the initial compound 4. X-ray crystallographic studies revealed two novel binding modes to the catalytic site of the PDE10A enzyme. (C) 2012 Elsevier Ltd. All rights reserved.