3-allyl-5-(quinoxalin-2-ylmethylene)-2-thioxothiazolidin-4-one | 896578-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-allyl-5-(quinoxalin-2-ylmethylene)-2-thioxothiazolidin-4-one
• 英文别名: 3-prop-2-enyl-5-(quinoxalin-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 896578-42-0
• 化学式: C₁₅H₁₁N₃OS₂
• 分子量: 313.404
• InChiKey: XODMZNKPVNIMSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.09
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-喹喔啉甲醛 、 3-丙烯基洛丹宁 以 乙醇 为溶剂， 反应 0.92h， 以60%的产率得到3-allyl-5-(quinoxalin-2-ylmethylene)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  The Rhodadyns, a New Class of Small Molecule Inhibitors of Dynamin GTPase Activity

  摘要：

  Six focused rhodanine-based libraries, 60 compounds in total, were synthesized and evaluated as potential dynamin I GTPase inhibitors. Twenty-six were more potent than the lead compound with 13 returning IC50 values <10 mu M, making the Rhodadyn series among the most active dynamin inhibitors reported. Two analogues were highly effective at blocking receptor-mediated endocytosis: C10 and D10 with IC50(RmE) = 7.0 +/- 2.2 and 5.9 +/- 1.0 mu M, respectively. These compounds are equipotent with the best reported in-cell dynamin inhibitors.

  DOI：

  10.1021/ml200284s

文献信息

• The Rhodadyns, a New Class of Small Molecule Inhibitors of Dynamin GTPase Activity
  作者：Mark J. Robertson、Gordana Hadzic、Joseph Ambrus、D. Yuri Pomè、Emily Hyde、Ainslie Whiting、Anna Mariana、Lisa von Kleist、Ngoc Chau、Volker Haucke、Phillip J. Robinson、Adam McCluskey

  DOI：10.1021/ml200284s

  日期：2012.5.10

  Six focused rhodanine-based libraries, 60 compounds in total, were synthesized and evaluated as potential dynamin I GTPase inhibitors. Twenty-six were more potent than the lead compound with 13 returning IC50 values <10 mu M, making the Rhodadyn series among the most active dynamin inhibitors reported. Two analogues were highly effective at blocking receptor-mediated endocytosis: C10 and D10 with IC50(RmE) = 7.0 +/- 2.2 and 5.9 +/- 1.0 mu M, respectively. These compounds are equipotent with the best reported in-cell dynamin inhibitors.