3,4-dihydro-1'(3')H-[4,4']biimidazolyl-2,5-dione | 91184-52-0

• 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: 3,4-dihydro-1'(3')H-[4,4']biimidazolyl-2,5-dione
• 英文别名: 5-Imidazolyl-(4)-hydantoin；5-(3H-imidazol-4-yl)imidazolidine-2,4-dione；5-(1H-imidazol-5-yl)imidazolidine-2,4-dione
• CAS: 91184-52-0
• 化学式: C₆H₆N₄O₂
• 分子量: 166.139
• InChiKey: HQZRIVXKNRQZAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  253-262 °C (decomp)
• 密度：
  1.517±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  86.9
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-1'(3')H-[4,4']biimidazolyl-2,5-dione 在 水 、 barium carbonate 作用下， 反应 72.0h， 以55%的产率得到D,L-4-咪唑基甘氨酸
  参考文献：
  名称：

  Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system over the vesicular glutamate transporter

  摘要：

  A panel of amino acid analogs and conformationally-restricted amino acids bearing a sulfonic acid were synthesized and tested for their ability to preferentially inhibit the obligate cysteine-glutamate transporter system x(c)(-) versus the vesicular glutamate transporter (VGLUT). Several promising candidate molecules were identified: R/S-4-[4'-carboxyphenyl]-phenylglycine, a biphenyl substituted analog of 4-carboxyphenylglycine and 2-thiopheneglycine-5-sulfonic acid both of which reduced glutamate uptake at system x(c)(-) by 70-75% while having modest to no effect on glutamate uptake at VGLUT. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.020
• 作为产物：
  描述：

  4-咪唑甲醛 、 碳酸氢铵 在 potassium cyanide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以75%的产率得到3,4-dihydro-1'(3')H-[4,4']biimidazolyl-2,5-dione
  参考文献：
  名称：

  Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system over the vesicular glutamate transporter

  摘要：

  A panel of amino acid analogs and conformationally-restricted amino acids bearing a sulfonic acid were synthesized and tested for their ability to preferentially inhibit the obligate cysteine-glutamate transporter system x(c)(-) versus the vesicular glutamate transporter (VGLUT). Several promising candidate molecules were identified: R/S-4-[4'-carboxyphenyl]-phenylglycine, a biphenyl substituted analog of 4-carboxyphenylglycine and 2-thiopheneglycine-5-sulfonic acid both of which reduced glutamate uptake at system x(c)(-) by 70-75% while having modest to no effect on glutamate uptake at VGLUT. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.020

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.