1-thieno[2,3-b]thiophen-2-yl-ethanone oxime | 1027982-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 1-thieno[2,3-b]thiophen-2-yl-ethanone oxime
• 英文别名: 1-Thieno[2,3-b]thiophen-2-yl-aethanon-oxim；(NE)-N-(1-thieno[2,3-b]thiophen-5-ylethylidene)hydroxylamine
• CAS: 1027982-05-3
• 化学式: C₈H₇NOS₂
• 分子量: 197.282
• InChiKey: LEJDRWDUYXIBQC-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-thieno[2,3-b]thiophen-2-yl-ethanone oxime 在 盐酸 、 吡啶硼烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.17h， 生成 N-hydroxy-N-(1-thieno[2,3-b]thien-2-ylethyl)urea
  参考文献：
  名称：

  Structure−Activity Relationships of N-Hydroxyurea 5-Lipoxygenase Inhibitors

  摘要：

  The discovery of second generation N-hydroxyurea 5-lipoxygenase inhibitors was accomplished through the development of a broad structure-activity relationship (SAR) study. This study identified requirements for improving potency and also extending duration by limiting metabolism. Potency could be maintained by the incorporation of heterocyclic templates substituted with selected lipophilic substituents. Duration of inhibition after oral administration was optimized by identification of structural features in the proximity of the N-hydroxyurea which correlated to low in vitro glucuronidation rates. Furthermore, the rate of in vitro glucuronidation was shown to be stereoselective for certain analogs. (R)-N-[3-[5-(4-Fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]-N-hy- droxyurea (17c) was identified and selected for clinical development.

  DOI：

  10.1021/jm9700474
• 作为产物：
  描述：

  2-(1-oxoethyl)thieno<2,3-b>thiophene 在 乙醇 、 盐酸羟胺 、 barium carbonate 作用下， 生成 1-thieno[2,3-b]thiophen-2-yl-ethanone oxime
  参考文献：
  名称：

  Challenger; Harrison, Journal of the Institute of Petroleum, 1935, vol. 21, p. 135,152

  摘要：

  DOI：

文献信息

• Challenger; Emmott, Journal of the Institute of Petroleum, 1951, vol. 37, p. 396,401
  作者：Challenger、Emmott

  DOI：——

  日期：——
• Structure−Activity Relationships of <i>N</i>-Hydroxyurea 5-Lipoxygenase Inhibitors
  作者：Andrew O. Stewart、Pramila A. Bhatia、Jonathan G. Martin、James B. Summers、Karen E. Rodriques、Michael B. Martin、James H. Holms、Jimmie L. Moore、Richard A. Craig、Teodozyj Kolasa、James D. Ratajczyk、Hormoz Mazdiyasni、Francis A. J. Kerdesky、Shari L. DeNinno、Robert G. Maki、Jennifer B. Bouska、Patrick R. Young、Carmine Lanni、Randy L. Bell、George W. Carter、Clint D. W. Brooks

  DOI：10.1021/jm9700474

  日期：1997.6.1

  The discovery of second generation N-hydroxyurea 5-lipoxygenase inhibitors was accomplished through the development of a broad structure-activity relationship (SAR) study. This study identified requirements for improving potency and also extending duration by limiting metabolism. Potency could be maintained by the incorporation of heterocyclic templates substituted with selected lipophilic substituents. Duration of inhibition after oral administration was optimized by identification of structural features in the proximity of the N-hydroxyurea which correlated to low in vitro glucuronidation rates. Furthermore, the rate of in vitro glucuronidation was shown to be stereoselective for certain analogs. (R)-N-[3-[5-(4-Fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]-N-hy- droxyurea (17c) was identified and selected for clinical development.
• Challenger; Harrison, Journal of the Institute of Petroleum, 1935, vol. 21, p. 135,152
  作者：Challenger、Harrison

  DOI：——

  日期：——