6,7-dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-2-propyl-1H-inden-1-one | 82749-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6,7-dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-2-propyl-1H-inden-1-one
• 英文别名: 6,7-dichloro-2-cyclopentyl-5-methoxy-2-propyl-3H-inden-1-one
• CAS: 82749-68-6
• 化学式: C₁₈H₂₂Cl₂O₂
• 分子量: 341.277
• InChiKey: AKJGYIHAQUAFQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,7-dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-2-propyl-1H-inden-1-one 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 17.5h， 生成
  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 、 1-碘代丙烷 在 sodium hydride 作用下， 生成 6,7-dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-2-propyl-1H-inden-1-one
  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：——
• Pharmaceutical compositions containing 4-((6,7-Dihalogen-2,3-dihydro-1-oxo-1H-inden-5-yl)-oxy) butanoic acid compounds
  申请人：Merck & Co., Inc.

  公开号：EP0047011B1

  公开（公告）日：1985-06-19
• US4465850A
  申请人：——

  公开号：US4465850A

  公开（公告）日：1984-08-14
• 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.