3-hydroxy-4-phenyl-1-(phenylmethyl)-1H-pyrrole-2,5-dione | 500291-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-hydroxy-4-phenyl-1-(phenylmethyl)-1H-pyrrole-2,5-dione
• 英文别名: 1-Benzyl-3-hydroxy-4-phenylpyrrole-2,5-dione
• CAS: 500291-41-8
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: MOBSIVQURLBUSI-UHFFFAOYSA-N

物化性质

• 沸点：
  472.8±45.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-phenyl-1-(phenylmethyl)-1H-pyrrole-2,5-dione 在 N,N-二甲基苯胺 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 LXRα/β激动剂
  参考文献：
  名称：

  Discovery of Substituted Maleimides as Liver X Receptor Agonists and Determination of a Ligand-Bound Crystal Structure

  摘要：

  Substituted 3-(phenylamino)-1H-pyrrole-2,5-diones were identified from a high throughput screen as inducers of human ATP binding cassette transporter A1 expression. Mechanism of action studies led to the identification of GSK3987 as an LXR ligand. GSK3987 recruits the steroid receptor coactivator-1 to human LXRalpha and LXRbeta with EC(50)s of 40 nM, profiles as an LXR agonist in functional assays, and activates LXR though a mechanism that is similar to first generation LXR agonists.

  DOI：

  10.1021/jm050532w
• 作为产物：
  描述：

  N-苄基苯乙酰胺 、 N,N-二甲基甲酰胺 在 potassium tert-butylate 作用下， 反应 14.5h， 以87%的产率得到3-hydroxy-4-phenyl-1-(phenylmethyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Discovery of Substituted Maleimides as Liver X Receptor Agonists and Determination of a Ligand-Bound Crystal Structure

  摘要：

  Substituted 3-(phenylamino)-1H-pyrrole-2,5-diones were identified from a high throughput screen as inducers of human ATP binding cassette transporter A1 expression. Mechanism of action studies led to the identification of GSK3987 as an LXR ligand. GSK3987 recruits the steroid receptor coactivator-1 to human LXRalpha and LXRbeta with EC(50)s of 40 nM, profiles as an LXR agonist in functional assays, and activates LXR though a mechanism that is similar to first generation LXR agonists.

  DOI：

  10.1021/jm050532w

文献信息

• 一种手性3,4-二取代琥珀酰亚胺及其衍生物的制备方法
  申请人：南方科技大学

  公开号：CN113683549A

  公开（公告）日：2021-11-23

  一种手性3,4‑二取代琥珀酰亚胺及其衍生物的制备方法，手性3,4‑二取代琥珀酰亚胺类化合物的制备方法，包括：在金属催化剂的存在下，使用式(I)所示的化合物反应得到式(II)所示的化合物。本发明提供的手性3,4‑二取代琥珀酰亚胺的制备方法，通过将式(I)所示的化合物在特定的金属催化剂作用下反应，得到式(II)所示的化合物，通过实验发现，该反应通过采用不对称转移氢化反应，不仅具有反应条件温和、收率高、产物的非对映选择性和对映选择性优异等优点，且反应体系中催化剂用量少，催化效率高。
• Discovery of Substituted Maleimides as Liver X Receptor Agonists and Determination of a Ligand-Bound Crystal Structure
  作者：Michael C. Jaye、John A. Krawiec、Nino Campobasso、Angela Smallwood、Chunyan Qiu、Quinn Lu、John J. Kerrigan、Maite De Los Frailes Alvaro、Bryan Laffitte、Wu-Schyong Liu、Joseph P. Marino,、Craig R. Meyer、Jason A. Nichols、Derek J. Parks、Paloma Perez、Lea Sarov-Blat、Sheila D. Seepersaud、Klaudia M. Steplewski、Scott K. Thompson、Ping Wang、Mike A. Watson、Christine L. Webb、David Haigh、Justin A. Caravella、Colin H. Macphee、Timothy M. Willson、Jon L. Collins

  DOI：10.1021/jm050532w

  日期：2005.8.1

  Substituted 3-(phenylamino)-1H-pyrrole-2,5-diones were identified from a high throughput screen as inducers of human ATP binding cassette transporter A1 expression. Mechanism of action studies led to the identification of GSK3987 as an LXR ligand. GSK3987 recruits the steroid receptor coactivator-1 to human LXRalpha and LXRbeta with EC(50)s of 40 nM, profiles as an LXR agonist in functional assays, and activates LXR though a mechanism that is similar to first generation LXR agonists.