9-hydroxy-9-(4-carboxyphenyl)fluorene | 219829-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-hydroxy-9-(4-carboxyphenyl)fluorene
• 英文别名: 4-(9-Hydroxyfluoren-9-yl)benzoic acid
• CAS: 219829-02-4
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: GMUWOSGBPVJGEB-UHFFFAOYSA-N

物化性质

• 沸点：
  531.783±38.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.371±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-hydroxy-9-(4-carboxyphenyl)fluorene 在 palladium dihydroxide 、 甲烷 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 4-(9H-fluoren-9-yl)benzoic acid
  参考文献：
  名称：

  Fluorenylalkanoic and Benzoic Acids as Novel Inhibitors of Cell Adhesion Processes in Leukocytes

  摘要：

  A series of fluoren-9-ylalkanoic and alkylbenzoic acids was prepared as simplified analogues of a previously reported series of antiinflammatory agents which act to inhibit neutrophil recruitment into inflamed tissue. The previous compounds (''leumedins'') contained (alkoxycarbonyl)amino or benzoic acid moieties tethered to a fluorene ring. This functionality was replaced with simple structural elements. The new compounds were, in general, found to be more potent than the earlier series at inhibiting adherence of neutrophils to serum-coated wells or endothelial cells in vitro. Compound 9 was approximately 10-fold more potent than the previously reported FMOC-phenylalanine, of which it is an analogue. Similarly, compound 19 was superior in potency to its first generation progenitor, NPC 16570. The new compounds were shown to inhibit neutrophil adherence under conditions in which adherence is mediated by Mac-1 (CD11b/CD18) and LFA-1 (CD11a/CD18); they thus appear to target beta(2)-integrins in their antiadhesion activity. These compounds provide a departure point for the further development of new cell adhesion inhibitors which should exhibit enhanced potency and a more selective mode of action.

  DOI：

  10.1021/jm00010a009
• 作为产物：
  描述：

  9-(4-甲基苯基)芴-9-醇 在 potassium permanganate 作用下， 以 吡啶 为溶剂， 以75%的产率得到9-hydroxy-9-(4-carboxyphenyl)fluorene
  参考文献：
  名称：

  9-Hydroxy-9-(4-carboxyphenyl)fluorene — a new linker for solid phase synthesis

  摘要：

  The convenient synthesis of 9-hydroxy-9-(4-carboxyphenyl)fluorene and its application as a new linker for solid phase synthesis is reported. The loading of the resin-bound linker with carboxylic acids as well as the cleavage conditions were investigated. The release of the carboxylic acids from this system by treatment with acids is hampered due to the electron-withdrawing effect of the carboxamide group in the para position of the phenyl ring of the resin-bound linker, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02192-3

文献信息

• 9-Hydroxy-9-(4-carboxyphenyl)fluorene — a new linker for solid phase synthesis
  作者：Bernd Henkel、Ernst Bayer

  DOI：10.1016/s0040-4039(98)02192-3

  日期：1998.12

  The convenient synthesis of 9-hydroxy-9-(4-carboxyphenyl)fluorene and its application as a new linker for solid phase synthesis is reported. The loading of the resin-bound linker with carboxylic acids as well as the cleavage conditions were investigated. The release of the carboxylic acids from this system by treatment with acids is hampered due to the electron-withdrawing effect of the carboxamide group in the para position of the phenyl ring of the resin-bound linker, (C) 1998 Elsevier Science Ltd. All rights reserved.
• Fluorenylalkanoic and Benzoic Acids as Novel Inhibitors of Cell Adhesion Processes in Leukocytes
  作者：Gregory S. Hamilton、Richard E. Mewshaw、Carmen M. Bryant、Ying Feng、Gerda Endemann、Kip S. Madden、Jennifer E. Danczak、John Perumattam、Lawrence W. Stanton

  DOI：10.1021/jm00010a009

  日期：1995.5

  A series of fluoren-9-ylalkanoic and alkylbenzoic acids was prepared as simplified analogues of a previously reported series of antiinflammatory agents which act to inhibit neutrophil recruitment into inflamed tissue. The previous compounds (''leumedins'') contained (alkoxycarbonyl)amino or benzoic acid moieties tethered to a fluorene ring. This functionality was replaced with simple structural elements. The new compounds were, in general, found to be more potent than the earlier series at inhibiting adherence of neutrophils to serum-coated wells or endothelial cells in vitro. Compound 9 was approximately 10-fold more potent than the previously reported FMOC-phenylalanine, of which it is an analogue. Similarly, compound 19 was superior in potency to its first generation progenitor, NPC 16570. The new compounds were shown to inhibit neutrophil adherence under conditions in which adherence is mediated by Mac-1 (CD11b/CD18) and LFA-1 (CD11a/CD18); they thus appear to target beta(2)-integrins in their antiadhesion activity. These compounds provide a departure point for the further development of new cell adhesion inhibitors which should exhibit enhanced potency and a more selective mode of action.