DIOA | 81166-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: DIOA
• 英文别名: 2-[[(2~{R})-2-butyl-6,7-bis(chloranyl)-2-cyclopentyl-1-oxidanylidene-3~{H}-inden-5-yl]oxy]ethanoic acid；2-[[(2R)-2-butyl-6,7-dichloro-2-cyclopentyl-1-oxo-3H-inden-5-yl]oxy]acetic acid
• CAS: 81166-47-4
• 化学式: C₂₀H₂₄Cl₂O₄
• 分子量: 399.314
• InChiKey: YAWWQIFONIPBKT-HXUWFJFHSA-N

物化性质

• 熔点：
  173-174 °C
• 沸点：
  562.2±50.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)
• 溶解度：
  H2O：不溶物，<0.11mg/mL
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

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：

  DIOA 在 盐酸 、 吡啶盐酸盐 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.25h， 生成 (+)-4-<(2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)oxy>butanoic 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
• 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 DIOA
  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
• 作为试剂：
  描述：

  (S)-3-甲基戊酸 、 (R)-4-异丙基-5,5-二苯基-2-恶唑烷酮 在 三甲基乙酰氯 、 DIOA 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以82%的产率得到(R)-4-isopropyl-3-[(S)-3-methyl-1-oxopentyl]-5,5-diphenyloxazolidin-2-one
  参考文献：
  名称：

  [EN] MASP INHIBITORY COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS INHIBITEURS DE MASP ET LEURS UTILISATIONS

  摘要：

  本发明涉及新型甘霖结合凝集素（MBL）相关丝氨酸蛋白酶（MASP）抑制化合物，以及其类似物和衍生物，以及其制备方法，单独或组合用于治疗和/或预防疾病，以及用于生产药物治疗和/或预防疾病，特别是用于治疗和/或预防肾脏和心血管疾病以及缺血再灌注损伤。

  公开号：

  WO2020225095A1

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：——
• SWELL1-LRRC8 COMPLEX MODULATORS
  申请人：Washington University

  公开号：US20220242812A1

  公开（公告）日：2022-08-04

  The present invention is directed to various polycyclic compounds and methods of using these compounds to treat a variety of diseases including metabolic diseases such as obesity, diabetes, nonalcoholic fatty liver disease; cardiovascular diseases such as hypertension and stroke; neurological diseases, male infertility, muscular disorders, and immune disorders.
• 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.