(1-Oxo-2-n-propyl-6,7-dichloro-5-indanyloxy)-acetic Acid | 55507-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1-Oxo-2-n-propyl-6,7-dichloro-5-indanyloxy)-acetic Acid
• 英文别名: 2-[(6,7-Dichloro-1-oxo-2-propyl-2,3-dihydroinden-5-yl)oxy]acetic acid
• CAS: 55507-82-9
• 化学式: C₁₄H₁₄Cl₂O₄
• 分子量: 317.169
• InChiKey: RSSGTKGXIHKGFE-UHFFFAOYSA-N

物化性质

• 熔点：
  203-205 °C(Solv: acetic acid (64-19-7); water (7732-18-5))
• 沸点：
  511.3±50.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (1-Oxo-2-n-propyl-6,7-dichloro-5-indanyloxy)-acetic Acid 在 四氢吡咯 、 盐酸 、 硫酸 、 1,5-二氮杂双环[4.3.0]壬-5-烯 、 溶剂黄146 作用下， 以 四氢呋喃 、 溶剂黄146 、 甲苯 为溶剂， 反应 20.5h， 生成 [(5,6-dichloro-3-oxo-9a-propyl-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]-acetic acid
  参考文献：
  名称：

  Agents for the treatment of brain edema. 2. [(2,3,9,9a-Tetrahydro-3-oxo-9a-substituted-1H-fluoren-7-yl)oxy]alkanoic acids and some of their analogs

  摘要：

  Our initial paper discussed brain edema resulting from traumatic head injury and the need for specific and effective agents to treat the disorder and disclosed a novel approach for the discovery of a drug of this kind. The current study describes the synthesis of a series of [(2,3,9,9a-tetrahydro-3-oxo-9a-substituted-1H-fluoren-7-yl)oxy]alk anoic acids and their analogues. These compounds were evaluated in an in vitro cerebrocortical tissue slice assay for their relative potencies in inhibiting K+ + HCO3- induced swelling. Structural modification at a number of sites in the "lead" compound revealed that significant biological activity was inherent only within a very narrow range of structural types. The observation that nearly all the biological activity resided in one of the two enantiomers demonstrated the marked stereospecificity of the most active compounds. One of the most potent compounds, (R)-(+)-[(5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren -7-yl) oxy]acetic acid ((+)-5c), exhibited a dose-response relationship in the in vivo acceleration/deceleration brain edema assay, and the data from the two highest doses were statistically significant. Electron microscopic examination demonstrated that the perivascular astroglial swelling that arises from this procedure is abolished in the animals treated with (+)-5c. This compound is currently being evaluated for its clinical efficacy and safety in the treatment of traumatic head injury.

  DOI：

  10.1021/jm00155a038
• 作为产物：
  描述：

  [2,3-dichloro-4-(2-methylene-1-oxopentyl)phenoxy]acetic acid 、 硫酸 以87%的产率得到
  参考文献：
  名称：

  WOLTERSDORF O. W. JR.; SOLMS S. J. DE; SCHULTZ E. M.; CRAGOE E. J. JR., J. MED. CHEM. , 1977, 20, NO 11, 1400-1408

  摘要：

  DOI：

文献信息

• [1-Hydroxy-5-indanyloxy (or thio)]-alkanoic acids
  申请人：Merck & Co., Inc.

  公开号：US04012524A1

  公开（公告）日：1977-03-15

  [1-Hydroxy-5-indanyloxy (or thio)]alkanoic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and hypouricemic activity. The acid products are prepared by several synthetic methods.

  揭示了1-羟基-5-茚氧（或硫）烷酸及其盐、酯和酰胺。这些产品在药用上具有双重作用，表现出利尿、排钠和降尿酸活性。这些酸产品可以通过几种合成方法制备。
• CRAGOE E. J.;WOLTERSDORF O. W.;GOULD N. P.;PIETRUSZKIEWICZ A. M.;ZIEGLER +, J. MED. CHEM., 1986, 29, N 5, 825-841
  作者：CRAGOE E. J.、WOLTERSDORF O. W.、GOULD N. P.、PIETRUSZKIEWICZ A. M.、ZIEGLER +

  DOI：——

  日期：——
• Tetrahydro-fluorene compounds, processes for their preparation and pharmaceutical compositions thereof
  申请人：Merck & Co., Inc.

  公开号：EP0027948B1

  公开（公告）日：1984-03-21
• US4012524A
  申请人：——

  公开号：US4012524A

  公开（公告）日：1977-03-15
• US4070539A
  申请人：——

  公开号：US4070539A

  公开（公告）日：1978-01-24