benzo[d]oxazole-7-yl methanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: benzo[d]oxazole-7-yl methanol
• 英文别名: benzo[d]oxazol-7-ylmethanol；Benzo[d]oxazol-7-ylmethanol；1,3-benzoxazol-7-ylmethanol
• 化学式: C₈H₇NO₂
• 分子量: 149.149
• InChiKey: YYMIZJSSOBXLKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzo[d]oxazole-7-yl methanol 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以56%的产率得到1,3-苯并恶唑-7-甲醛
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists

  摘要：

  N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2' and 3'-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2'-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2'-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.011
• 作为产物：
  描述：

  3-硝基水杨酸 在 lithium aluminium tetrahydride 、 硫酸 、 palladium on activated charcoal 、 氢气 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 为溶剂， 20.0~100.0 ℃ 、344.75 kPa 条件下， 反应 40.0h， 生成 benzo[d]oxazole-7-yl methanol
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists

  摘要：

  N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2' and 3'-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2'-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2'-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.011

文献信息

• ＺＮＦ１４３阻害活性を有する化合物およびその利用
  申请人：株式会社ヤクルト本社

  公开号：JP2016124812A

  公开（公告）日：2016-07-11

  【課題】ZNF143阻害効果を有する化合物並びにこれを含むZNF143阻害剤及び医薬組成物の提供。【解決手段】式（Ｉ）で表される化合物又はその塩並びにそれを含むZNF143阻害剤及びそれを有効成分とする医薬組成物。Ａ−Ｂ−Ｃ−Ｄ（Ｉ）［ＡはＨ、メチル基、ナフチル基、フェニル基又は含窒素複素環；Ｂは、であり、Ｃは、アミド結合又はＮとＯを含有する複素芳香環；Ｄは置換／未置換のフェニル基又は単環のＮ或いはＳを含む複素芳香環；Ｃ及びＤは共に、置換基を有していてもよい縮合複素環等］【選択図】図１

  提供具有ZNF143抑制作用的化合物以及包含该化合物的ZNF143抑制剂和药物组合物。通过式（I）表示的化合物或其盐，以及包含它的ZNF143抑制剂和以其为有效成分的药物组合物。A-B-C-D（I）[其中A为氢、甲基、萘基、苯基或含氮杂环；B为，C为，含有酰胺键或含氮和氧的复杂芳香环；D为取代/未取代的苯基或含有单环的N或S的复杂芳香环；C和D均可具有取代基，也可以是融合的复杂环等]【选图】图1
• Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists
  作者：Martin Hansen、Stine Engesgaard Jacobsen、Shane Plunkett、Gudrun Eckhard Liebscher、John D. McCorvy、Hans Bräuner-Osborne、Jesper Langgaard Kristensen

  DOI：10.1016/j.bmc.2014.12.011

  日期：2015.7

  N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2' and 3'-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2'-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2'-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines. (C) 2014 Elsevier Ltd. All rights reserved.