6-{[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methoxy}[1,2,4]triazolo [3,4-a]phthalazine | 851679-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-{[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methoxy}[1,2,4]triazolo [3,4-a]phthalazine
• 英文别名: Tert-butyl-dimethyl-[[6-([1,2,4]triazolo[3,4-a]phthalazin-6-yloxymethyl)pyridin-2-yl]methoxy]silane
• CAS: 851679-43-1
• 化学式: C₂₂H₂₇N₅O₂Si
• 分子量: 421.574
• InChiKey: BUAXYJHLMAJZFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-{[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methoxy}[1,2,4]triazolo [3,4-a]phthalazine 在 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Identification and synthesis of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to the α2δ-1 subunit of voltage gated calcium channel

  摘要：

  We have identified and synthesized a series of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to alpha(2)delta-1 subunit of voltage gated calcium channels. Structure-activity relationship studies directed toward improving the potency and physical properties of 2 lead to the discovery of 20 (IC50 = 15 nM) and (S)-22 (IC50 = 30 nM). A potent and selective radioligand, [H-3]-(S)-22 was also synthesized to demonstrate that this ligand binds to the same site as gabapentin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.008
• 作为产物：
  描述：

  6-氯-[1,2,4]噻唑并[3,4-a]二氮杂萘 、 (6-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)methanol 在 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-{[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methoxy}[1,2,4]triazolo [3,4-a]phthalazine
  参考文献：
  名称：

  Identification and synthesis of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to the α2δ-1 subunit of voltage gated calcium channel

  摘要：

  We have identified and synthesized a series of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to alpha(2)delta-1 subunit of voltage gated calcium channels. Structure-activity relationship studies directed toward improving the potency and physical properties of 2 lead to the discovery of 20 (IC50 = 15 nM) and (S)-22 (IC50 = 30 nM). A potent and selective radioligand, [H-3]-(S)-22 was also synthesized to demonstrate that this ligand binds to the same site as gabapentin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.008

文献信息

• Identification and synthesis of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to the α2δ-1 subunit of voltage gated calcium channel
  作者：Alec D. Lebsack、Janet Gunzner、Bowei Wang、Richard Pracitto、Hervé Schaffhauser、Angelina Santini、Jayashree Aiyar、Robert Bezverkov、Benito Munoz、Wensheng Liu、Shankar Venkatraman

  DOI：10.1016/j.bmcl.2004.03.008

  日期：2004.5

  We have identified and synthesized a series of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to alpha(2)delta-1 subunit of voltage gated calcium channels. Structure-activity relationship studies directed toward improving the potency and physical properties of 2 lead to the discovery of 20 (IC50 = 15 nM) and (S)-22 (IC50 = 30 nM). A potent and selective radioligand, [H-3]-(S)-22 was also synthesized to demonstrate that this ligand binds to the same site as gabapentin. (C) 2004 Elsevier Ltd. All rights reserved.