spiro[9H-fluorene-9,4'-isothiazolidin]-3'-one 1',1'-dioxide | 132606-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: spiro[9H-fluorene-9,4'-isothiazolidin]-3'-one 1',1'-dioxide
• 英文别名: Spiro[9H-fluorene-9,4''-isothiazolidin]-3''-one 1'',1''-Dioxide；1,1-dioxospiro[1,2-thiazolidine-4,9'-fluorene]-3-one
• CAS: 132606-12-3
• 化学式: C₁₅H₁₁NO₃S
• 分子量: 285.323
• InChiKey: KWWKVMDNXVTDAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙基9H-芴-9-羧酸酯 在 sodium methylate 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 spiro[9H-fluorene-9,4'-isothiazolidin]-3'-one 1',1'-dioxide
  参考文献：
  名称：

  Spiro[fluoreneisothiazolidin]one dioxides: new aldose reductase and L-hexonate dehydrogenase inhibitors

  摘要：

  The first examples of spiro[fluorene-9,4'- and -9,5'-isothiazolidin]one dioxides (1 and 2) were synthesized and screened for activity as aldose reductase and L-hexonate dehydrogenase inhibitors. Compared to compounds 1, and 9,5'-compounds 2, synthesized from fluorene-9-sulfonamides by alkylation at C(9) with ethyl bromoacetate followed by cyclization, were more active, but relatively nonselective, inhibitors of aldose reductase and L-hexonate dehydrogenase, with IC50 values for in vitro inhibition of both enzymes on the order of 10(-7)-10(-8) M. However, the isomeric 9,4'-compounds 1, prepared by alkylation of fluorene-9-carboxylic acid esters with bromo- or iodo-methanesulfonamide followed by cyclization, were more selective inhibitors Of L-hexonate dehydrogenase with IC50 values of about 10(-6) M.

  DOI：

  10.1021/jm00115a011

文献信息

• DUPRIEST, MARK T.
  作者：DUPRIEST, MARK T.

  DOI：——

  日期：——
• US4968809A
  申请人：——

  公开号：US4968809A

  公开（公告）日：1990-11-06
• Spiro[fluoreneisothiazolidin]one dioxides: new aldose reductase and L-hexonate dehydrogenase inhibitors
  作者：Mark T. DuPriest、Brenda W. Griffin、Daniel Kuzmich、Loretta G. McNatt

  DOI：10.1021/jm00115a011

  日期：1991.11

  The first examples of spiro[fluorene-9,4'- and -9,5'-isothiazolidin]one dioxides (1 and 2) were synthesized and screened for activity as aldose reductase and L-hexonate dehydrogenase inhibitors. Compared to compounds 1, and 9,5'-compounds 2, synthesized from fluorene-9-sulfonamides by alkylation at C(9) with ethyl bromoacetate followed by cyclization, were more active, but relatively nonselective, inhibitors of aldose reductase and L-hexonate dehydrogenase, with IC50 values for in vitro inhibition of both enzymes on the order of 10(-7)-10(-8) M. However, the isomeric 9,4'-compounds 1, prepared by alkylation of fluorene-9-carboxylic acid esters with bromo- or iodo-methanesulfonamide followed by cyclization, were more selective inhibitors Of L-hexonate dehydrogenase with IC50 values of about 10(-6) M.