(-)-4-<(2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)oxy>acetic acid | 81166-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (-)-4-<(2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)oxy>acetic acid
• 英文别名: R-(+)-DIOA；R(+)-Butylindazone；2-[[(2S)-2-butyl-6,7-dichloro-2-cyclopentyl-1-oxo-3H-inden-5-yl]oxy]acetic acid
• CAS: 81166-48-5
• 化学式: C₂₀H₂₄Cl₂O₄
• 分子量: 399.314
• InChiKey: YAWWQIFONIPBKT-FQEVSTJZSA-N

物化性质

• 熔点：
  172.0-173.5 °C
• 沸点：
  562.2±50.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-4-<(2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)oxy>acetic acid 在 吡啶盐酸盐 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.25h， 生成 ethyl 4-[(2-butyl-6,7-dichloro-2-cyclopentyl-1-oxo-3H-inden-5-yl)oxy]butanoate
  参考文献：
  名称：

  Agents for the treatment of brain injury. 1. (Aryloxy)alkanoic acids

  摘要：

  Blunt and ischemic injuries of the brain have been shown to result in swelling that is predominantly limited to a single cell type, the astrocyte, within the complex cellular mosiac of cerebral gray matter. Evaluation of various diuretic (aryloxy)acetic acids in vitro using incubating cat brain slices and primary astrocyte cultures identified compounds with marked ability to inhibit brain tissue swelling. Some of the compounds significantly reduced the mortality and morbidity following acceleration/deceleration brain injury in anesthesized cats. A variety of (indanyloxy)alkanoic acids were synthesized which were analogous to the dually active (indanyloxy)acetic acids. Some of the 4-(indanyloxy)butanoic acids were found to be devoid of diuretic activity but to possess equal or greater activity than the dually active compounds in the in vitro and in vivo brain assays. Selected examples from both the (indanyloxy)acetic and 4-(indanyloxy)butanoic acid series showed marked chiral effects, with one enantiomer generally exhibiting a much greater activity than the other. A clinical study of severely head-injured patients treated with ethacrynic acid demonstrated a significantly improved outcome when compared to controls. These data suggest a clinical advantage for the nondiuretic (aryloxy)alkanoic acids which possess in vitro and in vivo activities in the cat brain assays that are comparable or superior to dually active compounds.

  DOI：

  10.1021/jm00347a017
• 作为产物：
  描述：

  6,7-dichloro-2-cyclopentyl-5-methoxy-2,3-dihydro-1H-inden-1-one 在 盐酸 、 吡啶盐酸盐 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成 (-)-4-<(2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)oxy>acetic acid
  参考文献：
  名称：

  Agents for the treatment of brain injury. 1. (Aryloxy)alkanoic acids

  摘要：

  Blunt and ischemic injuries of the brain have been shown to result in swelling that is predominantly limited to a single cell type, the astrocyte, within the complex cellular mosiac of cerebral gray matter. Evaluation of various diuretic (aryloxy)acetic acids in vitro using incubating cat brain slices and primary astrocyte cultures identified compounds with marked ability to inhibit brain tissue swelling. Some of the compounds significantly reduced the mortality and morbidity following acceleration/deceleration brain injury in anesthesized cats. A variety of (indanyloxy)alkanoic acids were synthesized which were analogous to the dually active (indanyloxy)acetic acids. Some of the 4-(indanyloxy)butanoic acids were found to be devoid of diuretic activity but to possess equal or greater activity than the dually active compounds in the in vitro and in vivo brain assays. Selected examples from both the (indanyloxy)acetic and 4-(indanyloxy)butanoic acid series showed marked chiral effects, with one enantiomer generally exhibiting a much greater activity than the other. A clinical study of severely head-injured patients treated with ethacrynic acid demonstrated a significantly improved outcome when compared to controls. These data suggest a clinical advantage for the nondiuretic (aryloxy)alkanoic acids which possess in vitro and in vivo activities in the cat brain assays that are comparable or superior to dually active compounds.

  DOI：

  10.1021/jm00347a017

文献信息

• CRAGOE, E. J. ,, JR;GOULD, N. P.;WOLTERSDORF, O. W. ,, JR;ZIEGLER, C., J. MED. CHEM., 1982, 25, N 5, 567-579
  作者：CRAGOE, E. J. ,, JR、GOULD, N. P.、WOLTERSDORF, O. W. ,, JR、ZIEGLER, C.

  DOI：——

  日期：——
• Agents for the treatment of brain injury. 1. (Aryloxy)alkanoic acids
  作者：E. J. Cragoe、N. P. Gould、O. W. Woltersdorf、C. Ziegler、R. S. Bourke、L. R. Nelson、H. K. Kimelberg、J. B. Waldman、A. J. Popp、N. Sedransk

  DOI：10.1021/jm00347a017

  日期：1982.5

  Blunt and ischemic injuries of the brain have been shown to result in swelling that is predominantly limited to a single cell type, the astrocyte, within the complex cellular mosiac of cerebral gray matter. Evaluation of various diuretic (aryloxy)acetic acids in vitro using incubating cat brain slices and primary astrocyte cultures identified compounds with marked ability to inhibit brain tissue swelling. Some of the compounds significantly reduced the mortality and morbidity following acceleration/deceleration brain injury in anesthesized cats. A variety of (indanyloxy)alkanoic acids were synthesized which were analogous to the dually active (indanyloxy)acetic acids. Some of the 4-(indanyloxy)butanoic acids were found to be devoid of diuretic activity but to possess equal or greater activity than the dually active compounds in the in vitro and in vivo brain assays. Selected examples from both the (indanyloxy)acetic and 4-(indanyloxy)butanoic acid series showed marked chiral effects, with one enantiomer generally exhibiting a much greater activity than the other. A clinical study of severely head-injured patients treated with ethacrynic acid demonstrated a significantly improved outcome when compared to controls. These data suggest a clinical advantage for the nondiuretic (aryloxy)alkanoic acids which possess in vitro and in vivo activities in the cat brain assays that are comparable or superior to dually active compounds.