trans-1-benzylazetidine-2,4-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-1-benzylazetidine-2,4-dicarboxylic acid dimethyl ester
• 英文别名: trans-Dimethyl 1-benzylazetidine-2,4-dicarboxylate；dimethyl (2S,4S)-1-benzylazetidine-2,4-dicarboxylate
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: COJVYCMOVXNWAM-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-1-benzylazetidine-2,4-dicarboxylic acid dimethyl ester 在 palladium dihydroxide 甲基锂 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 2.42h， 生成
  参考文献：
  名称：

  新型刚性谷氨酸类似物（+）-和（-）-反式-氮杂环丁烷-2,4-二羧酸及其N-甲基衍生物的合成及代谢型受体活性。

  摘要：

  DOI：

  10.1021/jm00070a016
• 作为产物：
  描述：

  2,4-二溴戊二酸 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 trans-1-benzylazetidine-2,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis and bioactivity of a new class of rigid glutamate analogs. Modulators of the N-methyl-D-aspartate receptor

  摘要：

  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.

  DOI：

  10.1021/jm00168a007

文献信息

• Synthesis of 3,6-diazabicyclo[3.1.1]heptanes as novel ligands for the opioid receptors
  作者：Giovanni Loriga、Ilaria Manca、Gabriele Murineddu、Giorgio Chelucci、Stefania Villa、Stefania Gessi、Lucio Toma、Giorgio Cignarella、Gerard A. Pinna

  DOI：10.1016/j.bmc.2005.09.045

  日期：2006.2

  In an effort to improve diazabicycloalkane-based opioid receptor ligands, N-3(6)-arylpropenyl-N-6(3)-propionyl-3,6-diazabicyclo[3.1.1]heptanes (3A,Ba-i) were synthesized and their affinity and selectivity towards mu-, delta- and kappa-receptors were evaluated. The results of the current study revealed a number of compounds (3Bb, 3Bg and 3Bh) having a high affinity for mu (Ki at mu-receptors ranging

  为了改善基于二氮杂双环烷的阿片受体配体，合成了N-3（6）-芳基丙烯基-N-6（3）-丙酰基-3,6-二氮杂双环[3.1.1]庚烷（3A，Ba-i）并评估了它们对mu，delta和kappa受体的亲和力和选择性。当前研究的结果表明，许多化合物（3Bb，3Bg和3Bh）对mu（mu受体在2.7至7.9 nM范围内的Ki）相对于delta（delta受体> 2000 nM时的Ki）具有很高的亲和力。与Kappa（Ki在kappa受体> 5000 nM时）受体相比。在3Aa / 3Ba对和3Bh对上进行的分子建模与以下假设相符：两个系列的化合物3A和3B与mu受体相互作用的方式非常不同。
• 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：——
• NOVEL CYCLIC LIPID DERIVATIVES AS POTENT PAF ANTAGONISTS
  申请人：POHANG IRON & STEEL CO., LTD.

  公开号：EP0607374A1

  公开（公告）日：1994-07-27
• 3,6-Diazabicyclo[3.1.1]Heptane Derivatives with Analgesic Activity
  申请人：Pinna Aime Gerard

  公开号：US20070225492A1

  公开（公告）日：2007-09-27

  The invention relates to compounds of general formula (I), wherein R and R 1 , different from one another, are: a C 2 -C 8 straight or branched acyl group; and a group of formula (II), wherein B and R 2 are as defined in the description. The compounds (I) have higher central analgesic activity than morphine and are substantially free from the side effects of morphine or other central analgesics. The invention further relates to a process for the preparation of the compounds (I).
• US5610310A
  申请人：——

  公开号：US5610310A

  公开（公告）日：1997-03-11