4-((9H-fluoren-9-yl)methyl)benzoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-((9H-fluoren-9-yl)methyl)benzoic acid
• 英文别名: 4-(9H-fluoren-9-ylmethyl)benzoic acid
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: ZZHUJYGTVYLQLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((9H-fluoren-9-yl)methyl)benzoic acid 在 sodium tetrahydroborate 、 硫酸二甲酯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 以83%的产率得到4-((9H-fluoren-9-yl)methyl)benzaldehyde
  参考文献：
  名称：

  [EN] NOVEL HDAC6 INHIBITORS AND THEIR USES
  [FR] NOUVEAUX INHIBITEURS DE HDAC6 ET LEURS UTILISATIONS

  摘要：

  本发明涉及小分子化合物及其作为HDAC抑制剂的用途以及在治疗各种疾病（如癌症）中的应用。本发明还涉及合成这些化合物的方法和治疗方法。H - L（HA），其中H是从（头基团1）、（头基团2）、（头基团3）、（头基团4）、（头基团5）和（头基团6）中选择的头基团。

  公开号：

  WO2016020369A1
• 作为产物：
  描述：

  (9H-fluoren-9-ylmethylene)-4-benzoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 4-((9H-fluoren-9-yl)methyl)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

文献信息

• HDAC6 inhibitors and their uses
  申请人：Universität Regensburg

  公开号：US10106540B2

  公开（公告）日：2018-10-23

  The present invention relates to small molecule compounds and their use as HDAC inhibitors and in the treatment of various diseases, such as cancer. The present invention further relates to methods of synthesizing the compounds and methods of treatment. H-L(HA), H is a head group selected from (head group 1), (head group 2), (head group 3), (head group 4), (head group 5) and (head group 6).

  本发明涉及小分子化合物及其作为 HDAC 抑制剂和治疗各种疾病（如癌症）的用途。本发明进一步涉及合成化合物的方法和治疗方法。H-L（HA），H 是选自（头组 1）、（头组 2）、（头组 3）、（头组 4）、（头组 5）和（头组 6）的头组。
• NOVEL HDAC6 INHIBITORS AND THEIR USES
  申请人：Universität Regensburg

  公开号：EP3177621A1

  公开（公告）日：2017-06-14
• [EN] NOVEL HDAC6 INHIBITORS AND THEIR USES<br/>[FR] NOUVEAUX INHIBITEURS DE HDAC6 ET LEURS UTILISATIONS
  申请人：UNIVERSITÄT REGENSBURG

  公开号：WO2016020369A1

  公开（公告）日：2016-02-11

  The present invention relates to small molecule compounds and their use as HDAC inhibitors and in the treatment of various diseases, such as cancer. The present invention further relates to methods of synthesizing the compounds and methods of treatment. H − L(HA), H is a head group selected from (head group 1), (head group 2), (head group 3), (head group 4), (head group 5) and (head group 6).

  本发明涉及小分子化合物及其作为HDAC抑制剂的用途以及在治疗各种疾病（如癌症）中的应用。本发明还涉及合成这些化合物的方法和治疗方法。H - L（HA），其中H是从（头基团1）、（头基团2）、（头基团3）、（头基团4）、（头基团5）和（头基团6）中选择的头基团。
• 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.