N-(1-(6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-yl)piperidin-4-yl)-6-fluoro-4-oxo-4H-chromene-2-carboxamide | 1027285-61-5

• 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: N-(1-(6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-yl)piperidin-4-yl)-6-fluoro-4-oxo-4H-chromene-2-carboxamide
• 英文别名: N-[1-(6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-7-yl)piperidin-4-yl]-6-fluoro-4-oxochromene-2-carboxamide
• CAS: 1027285-61-5
• 化学式: C₂₅H₂₃FN₂O₅
• 分子量: 450.466
• InChiKey: BMVVLXNEZZJMOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-氟色酮-2-羧酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(1-(6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-yl)piperidin-4-yl)-6-fluoro-4-oxo-4H-chromene-2-carboxamide
  参考文献：
  名称：

  Constrained 7-fluorocarboxychromone-4-aminopiperidine based Melanin-concentrating hormone receptor 1 antagonists: The effects of chirality on substituted indan-1-ylamines

  摘要：

  The incorporation of constrained tertiary amines into an existing class of N-benzyl-4-aminopiperidinyl chromone-based MCHrl antagonists led to the identification of a series of chiral racemic compounds that displayed good to excellent functional potency, binding affinity, and selectivity over the hERG channel. Further separation of two distinct chiral racemic compounds into their corresponding pairs of enantiomers revealed a considerable selectivity for MCHr1 for one configuration, in addition to a striking difference in oral exposure between one pair of enantiomers in diet-induced obese mice. Oral administration of the most potent compound in this class in the same animal model led to significant reduction of fat mass in a semi-chronic model for weight loss. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.061

文献信息

• Constrained 7-fluorocarboxychromone-4-aminopiperidine based Melanin-concentrating hormone receptor 1 antagonists: The effects of chirality on substituted indan-1-ylamines
  作者：Andrew J. Souers、Rajesh R. Iyengar、Andrew S. Judd、David W.A. Beno、Ju Gao、Gang Zhao、Michael E. Brune、James J. Napier、Mathew M. Mulhern、John K. Lynch、Jennifer C. Freeman、Dariusz Wodka、Chong J. Chen、H. Doug Falls、Sevan Brodjian、Brian D. Dayton、Gilbert J. Diaz、Eugene N. Bush、Robin Shapiro、Brian A. Droz、Victoria Knourek-Segel、Lisa E. Hernandez、Kennan C. Marsh、Regina M. Reilly、Hing L. Sham、Christine A. Collins、Philip R. Kym

  DOI：10.1016/j.bmcl.2006.11.061

  日期：2007.2

  The incorporation of constrained tertiary amines into an existing class of N-benzyl-4-aminopiperidinyl chromone-based MCHrl antagonists led to the identification of a series of chiral racemic compounds that displayed good to excellent functional potency, binding affinity, and selectivity over the hERG channel. Further separation of two distinct chiral racemic compounds into their corresponding pairs of enantiomers revealed a considerable selectivity for MCHr1 for one configuration, in addition to a striking difference in oral exposure between one pair of enantiomers in diet-induced obese mice. Oral administration of the most potent compound in this class in the same animal model led to significant reduction of fat mass in a semi-chronic model for weight loss. (c) 2006 Elsevier Ltd. All rights reserved.