2-[{6-[5-(4-chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethoxy]-indan-1-yl}-(2-hydroxy-ethyl)-amino]-ethanol | 935248-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-[{6-[5-(4-chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethoxy]-indan-1-yl}-(2-hydroxy-ethyl)-amino]-ethanol
• CAS: 935248-18-3
• 化学式: C₂₂H₂₄ClN₃O₄
• 分子量: 429.903
• InChiKey: TXWMDDDXVNPBBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  91.85
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-[{6-[5-(4-chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethoxy]-indan-1-yl}-(2-hydroxy-ethyl)-amino]-ethanol 在 氯化亚砜 、 四丁基氯化铵 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 17.0h， 生成 (1-(4-(6-((5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl)methoxy)-2,3-dihydro-1H-inden-1-yl)piperazin-1-yl)cyclopentyl)methanol
  参考文献：
  名称：

  A novel, non-substrate-based series of glycine type 1 transporter inhibitors derived from high-throughput screening

  摘要：

  The synthesis and structure-activity relationships (SAR) of a series of indane and tetralin inhibitors of the type 1 glycine transporter, derived from a high-throughput screening (HTS) hit, are described. Key modifications that reduced the 5HT1B receptor affinity of the HTS hit and the P450 2D6 inhibition of subsequent analogues are delineated. While these modifications led to potent and selective GlyT1 inhibitors, HERG affinity and human microsomal clearance remain an issue for this series of compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.109
• 作为产物：
  描述：

  6-[5-(4-chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethoxy]-indan-1-one 在 四丁基氯化铵 sodium tetrahydroborate 、 氯化亚砜 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 22.5h， 生成 2-[{6-[5-(4-chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethoxy]-indan-1-yl}-(2-hydroxy-ethyl)-amino]-ethanol
  参考文献：
  名称：

  A novel, non-substrate-based series of glycine type 1 transporter inhibitors derived from high-throughput screening

  摘要：

  The synthesis and structure-activity relationships (SAR) of a series of indane and tetralin inhibitors of the type 1 glycine transporter, derived from a high-throughput screening (HTS) hit, are described. Key modifications that reduced the 5HT1B receptor affinity of the HTS hit and the P450 2D6 inhibition of subsequent analogues are delineated. While these modifications led to potent and selective GlyT1 inhibitors, HERG affinity and human microsomal clearance remain an issue for this series of compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.109