ethyl (1R,2R)-2-(2-ethyl-1,3-benzoxazol-7-yl)cyclopropane-1-carboxylate

• 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: ethyl (1R,2R)-2-(2-ethyl-1,3-benzoxazol-7-yl)cyclopropane-1-carboxylate
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: QSERYIPBBVIIGP-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1R,2R)-2-(2-ethyl-1,3-benzoxazol-7-yl)cyclopropane-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 ((1R,2R)-2-(2-Ethylbenzo[d]oxazol-7-yl)cyclopropyl)methanol
  参考文献：
  名称：

  Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands

  摘要：

  A novel series of benzoxazole derivatives was synthesized and evaluated as melatoninergic ligands. The binding affinity of these compounds for human MT1 and MT2 receptors was determined using 2-[I-125]-iodomelatonin as the radioligand. The results of the SAR studies in this series led to the identification of compound 28, which exhibited better MT1 and MT2 receptor affinities than melatonin itself. This work also established the benzoxazole nucleus as a melatoninergic pharmacophore, which served as an isosteric replacement to the previously established alkoxyaryl core. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.052
• 作为产物：
  描述：

  反式-2-羟基-3-硝基肉桂酸乙酯 在 palladium on activated charcoal palladium diacetate 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醚 、 xylene 为溶剂， 生成 ethyl (1R,2R)-2-(2-ethyl-1,3-benzoxazol-7-yl)cyclopropane-1-carboxylate
  参考文献：
  名称：

  Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands

  摘要：

  A novel series of benzoxazole derivatives was synthesized and evaluated as melatoninergic ligands. The binding affinity of these compounds for human MT1 and MT2 receptors was determined using 2-[I-125]-iodomelatonin as the radioligand. The results of the SAR studies in this series led to the identification of compound 28, which exhibited better MT1 and MT2 receptor affinities than melatonin itself. This work also established the benzoxazole nucleus as a melatoninergic pharmacophore, which served as an isosteric replacement to the previously established alkoxyaryl core. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.052

文献信息

• Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands
  作者：Li-Qiang Sun、Jie Chen、Katherine Takaki、Graham Johnson、Lawrence Iben、Cathy D. Mahle、Elaine Ryan、Cen Xu

  DOI：10.1016/j.bmcl.2003.12.052

  日期：2004.3

  A novel series of benzoxazole derivatives was synthesized and evaluated as melatoninergic ligands. The binding affinity of these compounds for human MT1 and MT2 receptors was determined using 2-[I-125]-iodomelatonin as the radioligand. The results of the SAR studies in this series led to the identification of compound 28, which exhibited better MT1 and MT2 receptor affinities than melatonin itself. This work also established the benzoxazole nucleus as a melatoninergic pharmacophore, which served as an isosteric replacement to the previously established alkoxyaryl core. (C) 2003 Elsevier Ltd. All rights reserved.