(+/-)-(1R,2S)-diethyl 1,2-dimethylcyclopropane-1,2-dicarboxylate | 714-79-4

• 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: (+/-)-(1R,2S)-diethyl 1,2-dimethylcyclopropane-1,2-dicarboxylate
• 英文别名: cis-diethyl 1,2-dimethylcyclopropane-1,2-dicarboxylate；1,2-diethyl-1,2-cyclopropanedicarboxylate
• CAS: 714-79-4
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: PWKRQYJTZRQZQD-PHIMTYICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(1R,2S)-diethyl 1,2-dimethylcyclopropane-1,2-dicarboxylate 在 sodium hydroxide 、 氯化亚砜 作用下， 反应 6.0h， 生成 1,5-二甲基-3-氧杂二环[3.1.0]己烷-2,4-二酮
  参考文献：
  名称：

  Design, synthesis and activity of novel derivatives of Oxybutynin and Tolterodine

  摘要：

  Novel derivatives of Tolterodine (1) and Oxybutynin (2) have been designed using conformationally restricted azabicyclics as replacement for open-chain amines. The synthesis and structure-activity relationships are presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.036
• 作为产物：
  描述：

  甲基丙烯酸乙酯 、 2-氯丙酸乙酯 在 sodium hydride 作用下， 以 甲苯 为溶剂， 生成 (+/-)-(1R,2S)-diethyl 1,2-dimethylcyclopropane-1,2-dicarboxylate
  参考文献：
  名称：

  Design, synthesis and activity of novel derivatives of Oxybutynin and Tolterodine

  摘要：

  Novel derivatives of Tolterodine (1) and Oxybutynin (2) have been designed using conformationally restricted azabicyclics as replacement for open-chain amines. The synthesis and structure-activity relationships are presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.036

文献信息

• Asymmetric synthesis of 3,3,5,5-tetrasubstituted 1,2-dioxolanes: total synthesis of epiplakinic acid F
  作者：Xiang-Yin Tian、Jian-Wei Han、Qiong Zhao、Henry N. C. Wong

  DOI：10.1039/c4ob00448e

  日期：——

  The first enantioselective total synthesis of epiplakinic acid F (1) was achieved through a pivotal step involving a radical-mediated asymmetric peroxidation of vinylcyclopropanes with molecular oxygen to construct highly substituted 1,2-dioxolanes. Subsequent conversions of the chiral 1,2-dioxolanes led to total synthesis of epiplakinic acid F (1) and the confirmation of its absolute configuration

  表素酸F（1）的第一个对映选择性全合成是通过一个关键步骤实现的，该关键步骤涉及自由基环介导的乙烯基环丙烷与分子氧的不对称过氧化，以构建高度取代的1,2-二氧戊环。手性1，2-二氧戊环的后续转化导致了表观泛酸F（1）的全合成，并证实了其绝对构型。还制备了表素酸F甲酯（2）的对映体。
• Cyclopropane-1,2-dicarboxylic acids as new tools for the biophysical investigation of<i>O</i>-acetylserine sulfhydrylases by fluorimetric methods and saturation transfer difference (STD) NMR
  作者：Giannamaria Annunziato、Marco Pieroni、Roberto Benoni、Barbara Campanini、Thelma A. Pertinhez、Chiara Pecchini、Agostino Bruno、Joana Magalhães、Stefano Bettati、Nina Franko、Andrea Mozzarelli、Gabriele Costantino

  DOI：10.1080/14756366.2016.1218486

  日期：2016.11.4

  Cysteine is a building block for many biomolecules that are crucial for living organisms. O-Acetylserine sulfhydrylase (OASS), present in bacteria and plants but absent in mammals, catalyzes the last step of cysteine biosynthesis. This enzyme has been deeply investigated because, beside the biosynthesis of cysteine, it exerts a series of "moonlighting" activities in bacteria. We have previously reported a series of molecules capable of inhibiting Salmonella typhimurium (S. typhymurium) OASS isoforms at nanomolar concentrations, using a combination of computational and spectroscopic approaches. The cyclopropane-1,2-dicarboxylic acids presented herein provide further insights into the binding mode of small molecules to OASS enzymes. Saturation transfer difference NMR (STD-NMR) was used to characterize the molecule/ enzyme interactions for both OASS-A and B. Most of the compounds induce a several fold increase in fluorescence emission of the pyridoxal 5'-phosphate (PLP) coenzyme upon binding to either OASS-A or OASS-B, making these compounds excellent tools for the development of competition-binding experiments.
• Cyclopropane derivatives as potential human serine racemase inhibitors: unveiling novel insights into a difficult target
  作者：Claudia Beato、Chiara Pecchini、Chiara Cocconcelli、Barbara Campanini、Marialaura Marchetti、Marco Pieroni、Andrea Mozzarelli、Gabriele Costantino

  DOI：10.3109/14756366.2015.1057720

  日期：2016.7.3

  D-Serine is the co-agonist of NMDA receptors and binds to the so-called glycine site. D-Serine is synthesized by human serine racemase (SR). Over activation of NMDA receptors is involved in many neurodegenerative diseases and, therefore, the inhibition of SR might represent a novel strategy for the treatment of these pathologies. SR is a very difficult target, with only few compounds so far identified exhibiting weak inhibitory activity. This study was aimed at the identification of novel SR inhibitor by mimicking malonic acid, the best-known SR inhibitor, with a cyclopropane scaffold. We developed, synthesized, and tested a series of cyclopropane dicarboxylic acid derivatives, complementing the synthetic effort with molecular docking. We identified few compounds that bind SR in high micromolar range with a lack of significant correlation between experimental and predicted binding affinities. The thorough analysis of the results can be exploited for the development of more potent SR inhibitors.