AM-7585 | 1338229-46-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: AM-7585
• 英文别名: 1-Butanesulfonic acid, 4,4,4-trifluoro-, 5-cyano-6-(trifluoromethyl)-9H-xanthen-4-yl ester；[5-cyano-6-(trifluoromethyl)-9H-xanthen-4-yl] 4,4,4-trifluorobutane-1-sulfonate
• CAS: 1338229-46-1
• 化学式: C₁₉H₁₃F₆NO₄S
• 分子量: 465.373
• InChiKey: HQSKDKMKFHMNMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.8
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-氟-6-(三氟甲基)苯腈 在 四(三苯基膦)钯 、 barium hydroxide octahydrate 、 四丁基溴化铵 、 三溴化硼 、 sodium hydride 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 AM-7585
  参考文献：
  名称：

  Conformationally constrained analogs of BAY 59–3074 as novel cannabinoid receptor ligands

  摘要：

  To obtain information on the pharmacophoric requirements of the CB1/CB2 partial agonist BAY 59-3074 we have synthesized a series of new conformationally constrained dibenzofuran (4a-d) and dibenzopyran analogs (5). All constrained analogs exhibited reduced binding affinity at both cannabinoid receptor subtypes, suggesting that planar conformations of these ligands are less favored by both receptors. We also found that 4c, 4d, and 5 exhibited 3- to 12-fold selectivity for hCB2 over rCB1 receptors and may serve as new chemotypes for the development of CB2-selective cannabinergics. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.07.017

文献信息

• Conformationally constrained analogs of BAY 59–3074 as novel cannabinoid receptor ligands
  作者：Heidi Teng、Ganesh A. Thakur、Alexandros Makriyannis

  DOI：10.1016/j.bmcl.2011.07.017

  日期：2011.10

  To obtain information on the pharmacophoric requirements of the CB1/CB2 partial agonist BAY 59-3074 we have synthesized a series of new conformationally constrained dibenzofuran (4a-d) and dibenzopyran analogs (5). All constrained analogs exhibited reduced binding affinity at both cannabinoid receptor subtypes, suggesting that planar conformations of these ligands are less favored by both receptors. We also found that 4c, 4d, and 5 exhibited 3- to 12-fold selectivity for hCB2 over rCB1 receptors and may serve as new chemotypes for the development of CB2-selective cannabinergics. (C) 2011 Published by Elsevier Ltd.