α,α'-Dibromoglutaric anhydride | 121049-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: α,α'-Dibromoglutaric anhydride
• 英文别名: 3,5-Dibromo-dihydro-pyran-2,6-dione；3,5-dibromooxane-2,6-dione
• CAS: 121049-89-6
• 化学式: C₅H₄Br₂O₃
• 分子量: 271.893
• InChiKey: SHGKMZHCBCNDKW-UHFFFAOYSA-N

物化性质

• 沸点：
  346.2±42.0 °C(Predicted)
• 密度：
  2.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α,α'-Dibromoglutaric anhydride 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：

  戊二酸酐 生成 α,α'-Dibromoglutaric anhydride
  参考文献：
  名称：

  Synthesis and evaluation of novel azetidine analogs as potent inhibitors of vesicular [3H]dopamine uptake

  摘要：

  Lobelane analogs that incorporate a central piperidine or pyrrolidine moiety have previously been reported by our group as potent inhibitors of VMAT2 function. Further central ring size reduction of the piperidine moiety in lobelane to a four-membered heterocyclic ring has been carried out in the current study to afford novel cis-and trans-azetidine analogs. These azetidine analogs (15a-15c and 22a-22c) potently inhibited [H-3]dopamine (DA) uptake into isolated synaptic vesicles (K-i <= 66 nM). The cis-4-methoxy analog 22b was the most potent inhibitor (K-i = 24 nM), and was twofold more potent that either lobelane (2a, K-i = 45 nM) or norlobelane (2b, K-i = 43 nM). The trans-methylenedioxy analog, 15c (K-i = 31 nM), was equipotent with the cis-analog, 22b, in this assay. Thus, cis-and trans-azetidine analogs 22b and 15c represent potential leads in the discovery of new clinical candidates for the treatment of methamphetamine abuse. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.001

文献信息

• 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.

  本发明涉及新型的氮杂环丙烷及其衍生物，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利用这些化合物和组合物作为生物学工具和材料，以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.

  本发明涉及新型氮杂四环和其衍生物，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利用这些化合物和组合物作为生物工具和材料，用于表征兴奋性氨基酸受体系统的方法。本发明的另一个方面涉及一种治疗PCP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.
• KOZIKOWSKI, ALAN P.;TUCKMANTEL, WERNER;REYNOLDS, IAN J.;WROBLEWSKI, JARDA+, J. MED. CHEM., 33,(1990) N, C. 1561-1571
  作者：KOZIKOWSKI, ALAN P.、TUCKMANTEL, WERNER、REYNOLDS, IAN J.、WROBLEWSKI, JARDA+

  DOI：——

  日期：——
• Synthesis and evaluation of novel azetidine analogs as potent inhibitors of vesicular [3H]dopamine uptake
  作者：Derong Ding、Justin R. Nickell、Agripina G. Deaciuc、Narsimha Reddy Penthala、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.bmc.2013.08.001

  日期：2013.11

  Lobelane analogs that incorporate a central piperidine or pyrrolidine moiety have previously been reported by our group as potent inhibitors of VMAT2 function. Further central ring size reduction of the piperidine moiety in lobelane to a four-membered heterocyclic ring has been carried out in the current study to afford novel cis-and trans-azetidine analogs. These azetidine analogs (15a-15c and 22a-22c) potently inhibited [H-3]dopamine (DA) uptake into isolated synaptic vesicles (K-i <= 66 nM). The cis-4-methoxy analog 22b was the most potent inhibitor (K-i = 24 nM), and was twofold more potent that either lobelane (2a, K-i = 45 nM) or norlobelane (2b, K-i = 43 nM). The trans-methylenedioxy analog, 15c (K-i = 31 nM), was equipotent with the cis-analog, 22b, in this assay. Thus, cis-and trans-azetidine analogs 22b and 15c represent potential leads in the discovery of new clinical candidates for the treatment of methamphetamine abuse. (C) 2013 Elsevier Ltd. All rights reserved.