α,α'-dibromoglutaric acid methyl, t-butyl ester | 121049-93-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: α,α'-dibromoglutaric acid methyl, t-butyl ester
• 英文别名: t-butyl methyl 2,4-dibromoglutarate；5-O-tert-butyl 1-O-methyl 2,4-dibromopentanedioate
• CAS: 121049-93-2
• 化学式: C₁₀H₁₆Br₂O₄
• 分子量: 360.043
• InChiKey: JGBOVZDMWYUZPH-UHFFFAOYSA-N

物化性质

• 沸点：
  331.6±42.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α,α'-dibromoglutaric acid methyl, t-butyl ester 在 palladium on activated charcoal 、 Wilkinson's catalyst 吡啶 、 sodium tetrahydroborate 、 2,2'-二硫二吡啶 、 二苯基膦酰羟胺 、 氢气 、 二甲基亚砜 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 t-butyl-3-endo-phenoxyacetamido-2-oxo-1-azabicyclo<3.2.0>heptane-7-exo-carboxylate
  参考文献：
  名称：

  碳青霉烯酸的γ-内酰胺类似物

  摘要：

  描述了碳青霉烯酸的双环4,5-γ-内酰胺类似物[（4a，b），（5）]的合成和生物学评估。

  DOI：

  10.1039/c39850000194
• 作为产物：
  描述：

  2,4-二溴戊二酸 在 乙酰氯 作用下， 生成 α,α'-dibromoglutaric acid methyl, t-butyl ester
  参考文献：
  名称：

  碳青霉烯酸的γ-内酰胺类似物

  摘要：

  描述了碳青霉烯酸的双环4,5-γ-内酰胺类似物[（4a，b），（5）]的合成和生物学评估。

  DOI：

  10.1039/c39850000194

文献信息

• γ-Lactam analogues of carbapenicillanic acids
  作者：Jack E. Baldwin、Robert M. Adlington、Richard H. Jones、Christopher J. Schofield、Constantine Zaracostas、Colin W. Greengrass

  DOI：10.1016/s0040-4020(01)82070-6

  日期：1986.1

  biological activities of the γ-lactam analogues (-25), (-25) and (26) of carbapenicillanic acids are described. The strategy employed for the synthesis of effected construction of a γ-lactam onto a preformed azetidine, followed by direct amination of the lactam enolate (20) with diphenylphosphinoyl-hydroxylamine. X-ray crystallographic studies demonstrated that the analogues bore a strong morphological

  描述了碳青霉烯酸的γ-内酰胺类似物（-25），（- 25）和（26）的合成和生物活性。用于将有效的γ-内酰胺结构合成到预先形成的氮杂环丁烷上，然后用二苯基膦酰基-羟胺直接胺化内酰胺烯酸酯（20）的策略。X射线晶体学研究表明，类似物与碳青霉烯酸具有很强的形态相似性。然而，它们被证明没有抗菌和β-内酰胺酶抑制活性。1个
• Azetidine derivatives, compositions and methods of treating
  申请人：Fidia-Georgetown Institute for the Neurosciences

  公开号：US04946839A1

  公开（公告）日：1990-08-07

  This invention relates to novel azetidines and derivative thereof, as well as to pharmaceutical compositions and methods of treating memory and learning disorders. Another aspect of the invention relates to a method of utilizing the compounds and compositions as biological tools and materials for characterizing excitatory amino acid receptor systems. A further aspect of the invention relates to a method of treating PCP toxicity and abuse.

  本发明涉及新型氮杂四元环及其衍生物，以及制备治疗记忆和学习障碍的药物组合物和方法。本发明的另一个方面涉及利用化合物和组合物作为生物工具和材料来表征兴奋性氨基酸受体系统的方法。本发明的另一个方面涉及一种治疗PCP毒性和滥用的方法。
• Azetidine derivatives to treat memory and learning disorders
  申请人：FIDIA-Georgetown Institute for the Neurosciences

  公开号：US04990504A1

  公开（公告）日：1991-02-05

  This invention relates to novel azetidines and derivatives thereof, as well as to pharmaceutical compositions and methods of treating memory and learning disorders. Another aspect of the invention relates to a method of utilizing the compounds and compositions as biological tools and materials for characterizing excitatory amino acid receptor systems. A further aspect of the invention relates to a method of treating PCP toxicity and abuse.

  本发明涉及新型的氮杂四元环及其衍生物，以及制备药物组合物和治疗记忆和学习障碍的方法。本发明的另一个方面涉及将这些化合物和组合物作为生物学工具和材料用于表征兴奋性氨基酸受体系统的方法。本发明的进一步方面涉及一种治疗PCP中毒和滥用的方法。
• Azetidine derivatives, compositions and their use
  申请人：FIDIA-GEORGETOWN INSTITUTE FOR THE NEUROSCIENCES

  公开号：EP0299513A1

  公开（公告）日：1989-01-18

  This invention relates to novel azetidines and derivatives thereof, as well as to pharmaceutical compositions and their use for treating memory and learning disorders. Another aspect of the invention relates to a method of utilizing the compounds and compositions as biological tools and materials for characterizing excitatory amino acid receptor systems. A further aspect of the invention relates to a method of treating PCP toxicity and abuse.

  本发明涉及新型氮杂环丁烷及其衍生物，以及药物组合物及其用于治疗记忆和学习障碍的用途。本发明的另一方面涉及一种利用这些化合物和组合物作为生物工具和材料来表征兴奋性氨基酸受体系统的方法。本发明的另一方面涉及一种治疗五氯苯酚毒性和滥用的方法。
• Synthesis and bioactivity of a new class of rigid glutamate analogs. Modulators of the N-methyl-D-aspartate receptor
  作者：Alan P. Kozikowski、Werner Tuckmantel、Ian J. Reynolds、Jarda T. Wroblewski

  DOI：10.1021/jm00168a007

  日期：1990.6

  A variety of derivatives of azetidine-2,4-dicarboxylic acid were synthesized and examined for their ability to stimulate 45Ca2+ uptake in cultures of cerebellar granule cells. Of the compounds tested, the cis-azetidine-2,4-dicarboxylic acid (10f) was found to be the most potent agent in potentiating glutamate, aspartate, or N-methyl-D-aspartate (NMDA) stimulated 45Ca2+ uptake at the NMDA receptor. The mechanism of action of 10f was further investigated in [3H]MK-801 binding assays and [3H]GABA release from cultured embryonic rat forebrain neurons. All of the results from the functional studies of azetidine 10f are consistent with a selectivity of action at the NMDA receptor. Moreover, azetidine 10f appears to exhibit a dual type of action, behaving as a glutamate-like agonist at higher concentrations and as a positive modulator at concentrations below 50 microM.