2-(2-aminoethyl)-1,2,4-oxadiazolidine-3,5-dione hydrobromide | 83583-49-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2-aminoethyl)-1,2,4-oxadiazolidine-3,5-dione hydrobromide
• 英文别名: Quisqualamine hydrobromide；2-(2-aminoethyl)-1,2,4-oxadiazolidine-3,5-dione;hydrobromide
• CAS: 83583-49-7
• 化学式: BrH*C₄H₇N₃O₃
• 分子量: 226.03
• InChiKey: PZAQPYHHNBREAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.33
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-aminoethyl)-1,2,4-oxadiazolidine-3,5-dione hydrobromide 在 氢氧化钾 作用下， 反应 0.5h， 以78%的产率得到2-(2-氨基-乙基)-[1,2,4]噁二唑-3,5-二酮
  参考文献：
  名称：

  A Selective and Efficient Synthesis of Quisqualamine, a Novel GABA-Related Depressant Amino Acid

  摘要：

  DOI：

  10.1055/s-1982-29944
• 作为产物：
  描述：

  N-Acetylquisqualamine 在 氢溴酸 作用下， 反应 10.0h， 以45%的产率得到2-(2-aminoethyl)-1,2,4-oxadiazolidine-3,5-dione hydrobromide
  参考文献：
  名称：

  A Selective and Efficient Synthesis of Quisqualamine, a Novel GABA-Related Depressant Amino Acid

  摘要：

  DOI：

  10.1055/s-1982-29944

文献信息

• [[2-(amino-3,4-dioxo-1-cyclobuten-1-yl) amino]alkyl]-acid derivatives
  申请人：American Home Products Corporation

  公开号：US05168103A1

  公开（公告）日：1992-12-01

  A compound of the formula: ##STR1## in which R.sup.1 is hydrogen, alkyl or phenylalkyl; R.sup.2 is hydrogen, alkyl, alkenyl or phenylalkyl; or R.sup.1 and R.sup.2 taken together are --Ch.sub.2 CH.sub.2 --, --CH.sub.2 C(R.sup.6)(R.sup.7)CH.sub.2 --or --CH.sub.2 C(R.sup.8)(R.sup.9)--C(R.sup.10)(R.sup.11)CH.sub.2 --, where R.sup.6, R.sup.8 and R.sup.10 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyl and R.sup.7, R.sup.9 and R.sup.11 are, independently, hydrogen or alkyl of 1 to 6 carbon atoms; A is alkylene or alkenylene; X is CO.sub.2 R.sup.3 in which R.sup.3 is hydrogen or alkyl, P(O)(OR.sup.4)(OR.sup.5) in which R.sup.4 and R.sup.5 are, independently, hydrogen or alkyl, 3,5-dioxo-1,2,4-oxadiazolindin-2-yl or 5-tetrazolyl; or a pharmaceutically acceptable salt thereof are useful as neuroprotectants.

  公式为：##STR1## 其中 R.sup.1 是氢、烷基或苯基烷基；R.sup.2 是氢、烷基、烯基或苯基烷基；或者 R.sup.1 和 R.sup.2 一起是 --Ch.sub.2 CH.sub.2 --，--CH.sub.2 C(R.sup.6)(R.sup.7)CH.sub.2 -- 或 --CH.sub.2 C(R.sup.8)(R.sup.9)--C(R.sup.10)(R.sup.11)CH.sub.2 --，其中 R.sup.6、R.sup.8 和 R.sup.10 独立地是氢、1 到 6 个碳原子的烷基或羟基，而 R.sup.7、R.sup.9 和 R.sup.11 独立地是氢或 1 到 6 个碳原子的烷基；A 是烷基或烯基；X 是 CO.sub.2 R.sup.3，其中 R.sup.3 是氢或烷基，P(O)(OR.sup.4)(OR.sup.5)，其中 R.sup.4 和 R.sup.5 独立地是氢或烷基，3,5-二氧代-1,2,4-噁二唑啉-2-基或 5-四唑基；或其药学上可接受的盐对神经保护剂具有用处。
• ((2-(amino-3,4-dioxo-1-cyclobuten-1-yl)amino)alkyl)-acid derivatives
  申请人：American Home Products Corporation

  公开号：US05240946A1

  公开（公告）日：1993-08-31

  A compound of the formula: ##STR1## in which R.sup.1 is hydrogen, alkyl or phenylalkyl; R.sup.2 is hydrogen, alkyl, alkenyl or phenylalkyl; or R.sup.1 and R.sup.2 taken together are --CH.sub.2 CH.sub.2 --, --CH.sub.2 C(R.sup.6)(R.sup.7)CH.sub.2 -- or --CH.sub.2 C(R.sup.8)(R.sup.9)--C(R.sup.10)(R.sup.11)CH.sub.2 --, where R.sup.6, R.sup.8 and R.sup.10 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyl and R.sup.7, R.sup.9 and R.sup.11 are, independently, hydrogen or alkyl of 1 to 6 carbon atoms; A is alkylene or alkenylene; X is CO.sub.2 R.sup.3 in which R.sup.3 is hydrogen or alkyl, P(O)(OR.sup.4)(OR.sup.5) in which R.sup.4 and R.sup.5 are, independently, hydrogen or alkyl, 3,5-dioxo-1,2,4-oxadiazolidin-2-yl or 5-tetrazolyl; or a pharmaceutically acceptable salt thereof are useful as neuroprotectants.

  该化合物的化学式为：##STR1## 其中R.sup.1为氢、烷基或苯基烷基；R.sup.2为氢、烷基、烯基或苯基烷基；或R.sup.1和R.sup.2在一起为--CH.sub.2 CH.sub.2 --、--CH.sub.2 C(R.sup.6)(R.sup.7)CH.sub.2 --或--CH.sub.2 C(R.sup.8)(R.sup.9)--C(R.sup.10)(R.sup.11)CH.sub.2 --，其中R.sup.6、R.sup.8和R.sup.10独立地为氢、1至6个碳原子的烷基或羟基，而R.sup.7、R.sup.9和R.sup.11独立地为氢或1至6个碳原子的烷基；A为烷基或烯基；X为CO.sub.2R.sup.3，其中R.sup.3为氢或烷基，P(O)(OR.sup.4)(OR.sup.5)，其中R.sup.4和R.sup.5独立地为氢或烷基，3,5-二氧代-1,2,4-噁二唑啉-2-基或5-四唑基；或其药学上可接受的盐对神经保护剂有用。
• Bioisosteric replacement of the .alpha.-amino carboxylic acid functionality in 2-amino-5-phosphonopentanoic acid yields unique 3,4-diamino-3-cyclobutene-1,2-dione containing NMDA antagonists
  作者：William A. Kinney、Nancy E. Lee、Deanna T. Garrison、Edward J. Podlesny、Joanne T. Simmonds、Donna Bramlett、Ronald R. Notvest、Dianne M. Kowal、Rene P. Tasse

  DOI：10.1021/jm00103a010

  日期：1992.12

  In this report, a novel bioisostere of the alpha-amino acid 3,4-diamino-3-cyclobutene-1,2-dione, has been incorporated into a series of compounds which are NMDA antagonists. These compounds, which are achiral and easily prepared, demonstrated good affinity at the NMDA receptor by their ability to displace [H-3]CPP binding in vitro. In particular, the phosphonic acid 24 provided protection against NMDA-induced lethality in mice equivalent to 2-amino-7-phosphonoheptanoic acid (5). This was considered an encouraging result in lieu of the fact that 24, like 5, lacks the conformational rigidity of the more potent NMDA antagonists. In addition, analogs that incorporate the 1,2,4-oxadiazolidine-3,5-dione heterocycle of quisqualic acid and the unsaturation of kainic acid were prepared to explore selectivity at the non-NMDA receptor subtypes.
• A Selective and Efficient Synthesis of Quisqualamine, a Novel GABA-Related Depressant Amino Acid
  作者：Philippe Dugenet、Jean Jacques Yaouanc、Georges Sturtz

  DOI：10.1055/s-1982-29944

  日期：——