8-chloro-2,3-dihydro-4H-1,5-naphtho<2,3-b>dioxepin-6,11-dione | 115943-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-chloro-2,3-dihydro-4H-1,5-naphtho<2,3-b>dioxepin-6,11-dione
• 英文别名: 8-chloro-2,3-dihydro-4H-1,5-naphtho[2,3-b]dioxepin-6,11-dione；8-chloro-3,4-dihydro-2H-benzo[h][1,5]benzodioxepine-6,11-dione
• CAS: 115943-50-5
• 化学式: C₁₃H₉ClO₄
• 分子量: 264.665
• InChiKey: QDZAORWYPWEFQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C
• 沸点：
  403.6±45.0 °C(predicted)
• 密度：
  1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-chloro-2,3-dihydro-4H-1,5-naphtho<2,3-b>dioxepin-6,11-dione 生成 (8-chloro-6-propanoyloxy-3,4-dihydro-2H-benzo[h][1,5]benzodioxepin-11-yl) propanoate
  参考文献：
  名称：

  JONES, GORDON H.;VENUTI, MICHAEL C.;YOUNG, JOHN M.

  摘要：

  DOI：
• 作为产物：
  描述：

  9-Amino-3,4-dihydro-2H-benzo[b][1,4]dioxepin-6-ol 在 sodium dichromate 、 硫酸 、 水 作用下， 反应 92.0h， 生成 8-chloro-2,3-dihydro-4H-1,5-naphtho<2,3-b>dioxepin-6,11-dione
  参考文献：
  名称：

  Topical nonsteroidal antipsoriatic agents. 2. 2,3-(Alkylidenedioxy)naphthalene analogs of lonapalene

  摘要：

  A series of 2,3-(alkylidenedioxy)naphthalene (5a-p) analogues of lonapalene (RS-43179, 1), a 5-lipoxygenase inhibitor currently under clinical investigation for the treatment of psoriasis, has been prepared and evaluated for topical inhibitory activity against arachidonic acid induced mouse ear edema. The results of these studies demonstrate that introduction of the fused 2,3-alkylidenedioxy ring, in place of the acyclic 2,3-dialkoxy substituent pattern characteristic of the previous series, caused a modest dimunition in overall potency within the series. These results suggest a potential steric intolerance for these extended planar analogues, in comparison with their 2,3-dialkoxy predecessors.

  DOI：

  10.1021/jm00119a013

文献信息

• JONES, GORDON H.;VENUTI, MICHAEL C.;YOUNG, JOHN M.
  作者：JONES, GORDON H.、VENUTI, MICHAEL C.、YOUNG, JOHN M.

  DOI：——

  日期：——
• VENUTI, MICHAEL C.;LOE, BRAD E.;JONES, GORDON H.;YOUNG, JOHN M., J. MED. CHEM., 31,(1988) N 11, C. 2132-2136
  作者：VENUTI, MICHAEL C.、LOE, BRAD E.、JONES, GORDON H.、YOUNG, JOHN M.

  DOI：——

  日期：——
• Topical nonsteroidal antipsoriatic agents. 2. 2,3-(Alkylidenedioxy)naphthalene analogs of lonapalene
  作者：Michael C. Venuti、Brad E. Loe、Gordon H. Jones、John M. Young

  DOI：10.1021/jm00119a013

  日期：1988.11

  A series of 2,3-(alkylidenedioxy)naphthalene (5a-p) analogues of lonapalene (RS-43179, 1), a 5-lipoxygenase inhibitor currently under clinical investigation for the treatment of psoriasis, has been prepared and evaluated for topical inhibitory activity against arachidonic acid induced mouse ear edema. The results of these studies demonstrate that introduction of the fused 2,3-alkylidenedioxy ring, in place of the acyclic 2,3-dialkoxy substituent pattern characteristic of the previous series, caused a modest dimunition in overall potency within the series. These results suggest a potential steric intolerance for these extended planar analogues, in comparison with their 2,3-dialkoxy predecessors.