6-(methylamino)hexane-1,2,3,4,5-pentol 4-(((1S,2R)-1-hydroxy-2,3-dihydro-1H,1'H-2,2'-biinden-2-yl)methyl)benzoate | 1380445-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 6-(methylamino)hexane-1,2,3,4,5-pentol 4-(((1S,2R)-1-hydroxy-2,3-dihydro-1H,1'H-2,2'-biinden-2-yl)methyl)benzoate
• 英文别名: 6-(methylamino)hexane-1,2,3,4,5-pentanol 4-(((1S,2R)-1-hydroxy-2,3-dihydro-1H,1'H-[2,2'-biinden]-2-yl)methyl)benzoate；4-(((1S,2S)-1-hydroxy-2,3-dihydro-1H,1'H-[2,2'-biinden]-2-yl)methyl)benzoic acid N-methyl-D-glucamine salt；4-(((1S,2R)-2,3-dihydro-1-hydroxy-2-(1H-inden-2-yl)-1H-inden-2-yl)methyl)benzoic acid N-methyl-D-glucamine salt；4-[[(1S,2R)-1-hydroxy-2-(1H-inden-2-yl)-1,3-dihydroinden-2-yl]methyl]benzoate;methyl-[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]azanium
• CAS: 1380445-13-5
• 化学式: C₇H₁₇NO₅*C₂₆H₂₂O₃
• 分子量: 577.675
• InChiKey: LJJBGRVJRGJEOO-SILHBEOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  171
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-trimethylsilyloxy-3H-indene 在 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 potassium tert-butylate 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 叔丁醇 为溶剂， 反应 30.0h， 生成 6-(methylamino)hexane-1,2,3,4,5-pentol 4-(((1S,2R)-1-hydroxy-2,3-dihydro-1H,1'H-2,2'-biinden-2-yl)methyl)benzoate
  参考文献：
  名称：

  6-(Methylamino)hexane-1,2,3,4,5-pentanol 4-(((1S,2S)-1-Hydroxy-2,3-dihydro-1H,1′H-[2,2-biinden]-2-yl)methyl)benzoate (PH46A): A Novel Small Molecule With Efficacy In Murine Models Of Colitis

  摘要：

  The indane skeleton is found naturally and in several therapeutic molecules in medicinal chemistry. During our work on the anti-inflammatory activity of naturally occurring and synthetic indanes, we have synthesized a novel indane scaffold that has been optimized for both anti-inflammatory activity and bioavailability. We have evaluated our lead molecule, PH46A, in in vivo models of inflammatory bowel disease (MD), an area of considerable unmet clinical need; current therapies are often unable to control the course of the disease. The compound significantly reduced histological damage and serum amyloid A (SAA) levels in IL-10(-/-) colitis mice, was efficacious in the 5% dextran sulfate sodium (DSS) colitis model, and compared favorably with prednisolone in this model and supports its potential use to treat acute exacerbations of the disease. Further, the graded response to the compound may also lend itself to be used at a lower dose to maintain periods of remission.

  DOI：

  10.1021/jm300390f

文献信息

• 6-(Methylamino)hexane-1,2,3,4,5-pentanol 4-(((1<i>S</i>,2<i>S</i>)-1-Hydroxy-2,3-dihydro-1<i>H</i>,1′<i>H</i>-[2,2-biinden]-2-yl)methyl)benzoate (PH46A): A Novel Small Molecule With Efficacy In Murine Models Of Colitis
  作者：Neil Frankish、Helen Sheridan

  DOI：10.1021/jm300390f

  日期：2012.6.14

  The indane skeleton is found naturally and in several therapeutic molecules in medicinal chemistry. During our work on the anti-inflammatory activity of naturally occurring and synthetic indanes, we have synthesized a novel indane scaffold that has been optimized for both anti-inflammatory activity and bioavailability. We have evaluated our lead molecule, PH46A, in in vivo models of inflammatory bowel disease (MD), an area of considerable unmet clinical need; current therapies are often unable to control the course of the disease. The compound significantly reduced histological damage and serum amyloid A (SAA) levels in IL-10(-/-) colitis mice, was efficacious in the 5% dextran sulfate sodium (DSS) colitis model, and compared favorably with prednisolone in this model and supports its potential use to treat acute exacerbations of the disease. Further, the graded response to the compound may also lend itself to be used at a lower dose to maintain periods of remission.