3-(2-呋喃基)丙烯醛肟 | 623-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 3-(2-呋喃基)丙烯醛肟
• 英文名称: 3-(2-furyl)propenal oxime
• 英文别名: 3-[2]furyl-acrylaldehyde-oxime；3-[2]Furyl-acrylaldehyd-oxim；3-(2-Furanyl)-2-propenal oxime；(NE)-N-[(E)-3-(furan-2-yl)prop-2-enylidene]hydroxylamine
• CAS: 623-31-4；123665-86-1
• 化学式: C₇H₇NO₂
• 分子量: 137.138
• InChiKey: GCQQNIZGZHEFKI-JOEIGAFWSA-N

物化性质

• 熔点：
  146-148 °C
• 沸点：
  249.1±32.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-呋喃基)丙烯醛肟 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-(3-fur-2-ylprop-2-enyl) 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

文献信息

• Synthesis and antimicrobial activity of O-aroylpyruvoyl- and O-aroylacetyloximes of aldehydes of the furan series
  作者：Yu. S. Andreichikov、D. D. Nekrasov、E. A. Kolevatova、M. A. Trushule

  DOI：10.1007/bf00766585

  日期：1990.12
• PINDUR U.; UNTERHALT B., ARCH. PHARM., 1979, 312, NO 4, 282-288
  作者：PINDUR U.、 UNTERHALT B.

  DOI：——

  日期：——
• ANDREJCHIKOV, YU. S.;NEKRASOV, D. D.;KOLEVATOVA, E. A.;TRUSHULE, M. A., XIM.-FARMATS. ZH., 24,(1990) N2, S. 33-35
  作者：ANDREJCHIKOV, YU. S.、NEKRASOV, D. D.、KOLEVATOVA, E. A.、TRUSHULE, M. A.

  DOI：——

  日期：——
• OSIPOVA M. P.; VOLKOVA R. V.; SPIRIDONOV E. A., ZH. OBSHCH. XIMII, 56,(1986) N 2, 328-330
  作者：OSIPOVA M. P.、 VOLKOVA R. V.、 SPIRIDONOV E. A.

  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.