5-[5-(2,5-Dioxoimidazolidin-4-yl)thiophen-2-yl]imidazolidine-2,4-dione | 1318796-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-[5-(2,5-Dioxoimidazolidin-4-yl)thiophen-2-yl]imidazolidine-2,4-dione
• CAS: 1318796-97-2
• 化学式: C₁₀H₈N₄O₄S
• 分子量: 280.264
• InChiKey: GDXBIXFUQNEBQP-UHFFFAOYSA-N

物化性质

• 密度：
  1.592±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  碳酸氢铵 、 potassium cyanide 、 2,5-噻吩二甲醛 以 甲醇 、 水 为溶剂， 反应 3.0h， 以68%的产率得到5-[5-(2,5-Dioxoimidazolidin-4-yl)thiophen-2-yl]imidazolidine-2,4-dione
  参考文献：
  名称：

  Use of the hydantoin isostere to produce inhibitors showing selectivity toward the vesicular glutamate transporter versus the obligate exchange transporter system

  摘要：

  Evidence was acquired prior to suggest that the vesicular glutamate transporter (VGLUT) but not other glutamate transporters were inhibited by structures containing a weakly basic a-amino group. To test this hypothesis, a series of analogs using a hydantoin (pK(a) similar to 9.1) isostere were synthesized and analyzed as inhibitors of VGLUT and the obligate cystine-glutamate transporter (system x(c)(-)). Of the hydantoin analogs tested, a thiophene-5-carboxaldehyde analog 2l and a bis-hydantoin 4b were relatively strong inhibitors of VGLUT reducing uptake to less than 6% of control at 5 mM but few inhibited system x(c)(-) greater than 50% of control. The benzene-2,4-disulfonic acid analog 2b and p-diaminobenzene analog 2e were also good hydantoin-based inhibitors of VGLUT reducing uptake by 11% and 23% of control, respectively, but neither analog was effective as a system x(c)(-) inhibitor. In sum, a hydantoin isostere adds the requisite chemical properties needed to produce selective inhibitors of VGLUT. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.018

文献信息

• Use of the hydantoin isostere to produce inhibitors showing selectivity toward the vesicular glutamate transporter versus the obligate exchange transporter system
  作者：S. Kaleem Ahmed、Jean-Louis G. Etoga、Sarjubhai A. Patel、Richard J. Bridges、Charles M. Thompson

  DOI：10.1016/j.bmcl.2011.05.018

  日期：2011.7

  Evidence was acquired prior to suggest that the vesicular glutamate transporter (VGLUT) but not other glutamate transporters were inhibited by structures containing a weakly basic a-amino group. To test this hypothesis, a series of analogs using a hydantoin (pK(a) similar to 9.1) isostere were synthesized and analyzed as inhibitors of VGLUT and the obligate cystine-glutamate transporter (system x(c)(-)). Of the hydantoin analogs tested, a thiophene-5-carboxaldehyde analog 2l and a bis-hydantoin 4b were relatively strong inhibitors of VGLUT reducing uptake to less than 6% of control at 5 mM but few inhibited system x(c)(-) greater than 50% of control. The benzene-2,4-disulfonic acid analog 2b and p-diaminobenzene analog 2e were also good hydantoin-based inhibitors of VGLUT reducing uptake by 11% and 23% of control, respectively, but neither analog was effective as a system x(c)(-) inhibitor. In sum, a hydantoin isostere adds the requisite chemical properties needed to produce selective inhibitors of VGLUT. (C) 2011 Elsevier Ltd. All rights reserved.