2,6-difluorofluoren-9-one | 2795-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,6-difluorofluoren-9-one
• 英文别名: 2,6-Difluor-9-oxo-fluoren；2,6-Difluor-fluorenon；2,6-Difluorfluorenon；2,6-Difluoro-9h-fluoren-9-one
• CAS: 2795-53-1
• 化学式: C₁₃H₆F₂O
• 分子量: 216.187
• InChiKey: TZVBQDDCBPJEKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-difluorofluoren-9-one 在 盐酸羟胺 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Identification, synthesis and pharmacological evaluation of novel anti-EV71 agents via cyclophilin A inhibition

  摘要：

  In this work, the relationship between cyclophilin A (CypA) and EV71 prompted us to screen a series of small molecular CypA inhibitors which were previously reported by our group. Among them, compounds 1 and 2 were discovered as non-immunosuppressive anti-EV71 agents with an EC50 values of 1.07 +/- 0.17 mu M and 3.36 +/- 0.45 mu M in virus assay, respectively, which were desirably for the further study. The subsequent chemical modifications derived a novel class of molecules, among which compound 11 demonstrated the most potent anti-EV71 activity in virus assay (EC50 = 0.37 +/- 0.17 mu M), and low cytotoxicity (CC50 > 25 mu M). The following CypA enzyme inhibition studies indicated that there was not only the enzyme inhibition activity, undoubtedly important, functioning in the antiviral process, but also some unknown mechanisms worked in combination, and the further study is underway in our laboratory. Nevertheless, to the best of our knowledge, compound 11 was probably the most potent small molecular anti-EV71 agent via CypA inhibitory mechanism to date. Consequently, our study provided a new potential small molecule for curing EV71 infection. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.002
• 作为产物：
  描述：

  4-氟苯甲酸酐 在 Wilkinson's catalyst 作用下， 生成 2,6-difluorofluoren-9-one
  参考文献：
  名称：

  Catalytic transformation of benzoic anhydrides into fluorenones and biphenyls

  摘要：

  DOI：

  10.1021/jo00835a010

文献信息

• [EN] METHOD OF INHIBITING ALDOSE REDUCTASE ACTIVITY, COMPOSITIONS THEREFOR AND PROCESS FOR PREPARING SPIRO-FLUOROFLUOREN AND SPIRO-DIFLUOROFLUOREN COMPOUNDS
  申请人：ALCON LABORATORIES, INC.

  公开号：WO1983003543A1

  公开（公告）日：1983-10-27

  (EN) Accumulation of polyols in diabetic subjects causes and/or is associated with diabetic complications. Aldose reductase inhibition prevents the production of polyols. Aldose reductase activity is inhibited with tetracyclic spiro-hydantoins, which makes these compounds useful in the treatment of complications arising from diabetes mellitus. A process for preparing said tetracyclic spiro-hydantoins by reacting a mono- or di-fluorofluorene with an excess of oxygen and a tetralkyl- or arylalkyl-trialkyl-ammonium hydroxides followed by cyclization of the reaction product with ammonium carbonate and potassium cyanide at elevated temperature is also disclosed. (FR) L'accumulation de polyols dans des sujets diabétiques est à l'origine de complications diabétiques et/ou s'associe à celle-ci. L'inhibition de l'aldose réductase empêche la production de polyols. L'activité d'aldose réductase est inhibée au moyen de spiro-hydantoïnes tétracycliques, ce qui rend ces composés utiles dans le traitement de complication résultant du diabète sucré. On décrit également un procédé de préparation de ces spiro-hydantoïnes tétracycliques en faisant réagir un mono- ou di-fluorofluorène avec un excédent d'oxygène et un hydroxyde de tétralkyl-ammonium ou d'arylalkyl-trialkyl-ammonium suivi par une cyclisation du produit de réaction avec du carbonate d'ammonium et du cyanure de potassium à une température élevée.

  (中文) 糖尿病患者中的多元醇积累导致或与糖尿病并发症有关。醛固酮还原酶抑制剂可以防止多元醇的产生。四环螺噻嗪可以抑制醛固酮还原酶活性，因此这些化合物在治疗糖尿病并发症方面非常有用。本文还介绍了一种制备四环螺噻嗪的方法，即通过将单氟芴或二氟芴与过量的氧和四烷基或芳基烷基三烷基铵氢氧化物反应，然后在高温下将反应产物与碳酸铵和氰化钾环化。
• Derivatives of Fluorene. X. Fluorofluorenes. III¹
  作者：T. LLOYD FLETCHER、MOSES J. NAMKUNG、WILLIAM H. WETZEL、HSI-LUNG PAN

  DOI：10.1021/jo01078a015

  日期：1960.8
• Derivatives of Fluorene. XXIII.¹ New Thiofluorenes Related to Metabolism of the Carcinogen N-2-Fluorenylacetamide
  作者：T. Lloyd. Fletcher、Moses J. Namkung、Hsi-Lung. Pan

  DOI：10.1021/jm00317a041

  日期：1967.9
• Hydantoin derivatives for use in inhibiting aldose reductase activity, compositions therefor and process for preparing spiro-fluoren compounds
  申请人：ALCON LABORATORIES, INC.

  公开号：EP0092385B1

  公开（公告）日：1991-06-12
• US4436745A
  申请人：——

  公开号：US4436745A

  公开（公告）日：1984-03-13